| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2023-05-30 20:55:51 UTC |
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| HMDB ID | HMDB0000132 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Guanine |
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| Description | Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Guanine nucleotide-binding regulatory proteins may be involved in the activation of phospholipases C and A2 by hormones and other ligands. The binding of hormones to receptors that activate phospholipase C is decreased by guanine nucleotides and these hormones also stimulate a high-affinity GTPase activity in cell membranes. Effects of hormones on phospholipase C activity in cell-free preparations are dependent on the presence of guanine nucleotides. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Partial deficiency of this enzyme can result in the overproduction of uric acid leading to a severe form of gout, whilst a virtual absence of HPRT activity causes the Lesch-Nyhan syndrome, an inborn error of metabolism, which is characterised by hyperuricaemia, mental retardation, choreoathetosis and compulsive self-mutilation. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin (PMID: 16352449 , 2435586 , 2838362 , 1487231 ). | Read more...
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| Structure | InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) |
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| Synonyms | | Value | Source |
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| 2-Amino-6-hydroxypurine | ChEBI | | 2-Amino-6-oxopurine | ChEBI | | G | ChEBI | | Gua | ChEBI | | 2-Amino-1,7-dihydro-6H-purin-6-one | HMDB | | 2-Amino-1,9-dihydro-6H-purin-6-one | HMDB | | 2-Amino-1,9-dihydro-purin-6-one | HMDB | | 2-Amino-3,7-dihydro-6H-purin-6-one | HMDB | | 2-Amino-6-hydroxy-1H-purine | HMDB | | 2-Amino-6-purinol | HMDB | | 2-Amino-hypoxanthine | HMDB | | 2-Aminohypoxanthine | HMDB | | 6-Hydroxy-2-aminopurine | HMDB | | C.I. natural white 1 | HMDB | | CI natural white 1 | HMDB | | Dew pearl | HMDB | | Guanin | HMDB | | Guanine enol | HMDB | | GUN | HMDB | | Mearlmaid | HMDB | | Mearlmaid aa | HMDB | | Natural pearl essence | HMDB | | Natural white 1 | HMDB | | Naturon | HMDB | | Pathocidin | HMDB | | Pearl essence | HMDB | | Stella polaris | HMDB |
| Show more...
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| Chemical Formula | C5H5N5O |
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| Average Molecular Weight | 151.1261 |
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| Monoisotopic Molecular Weight | 151.049409807 |
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| IUPAC Name | 2-amino-6,7-dihydro-3H-purin-6-one |
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| Traditional Name | 2-aminohypoxanthine |
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| CAS Registry Number | 73-40-5 |
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| SMILES | NC1=NC(=O)C2=C(N1)N=CN2 |
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| InChI Identifier | InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) |
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| InChI Key | UYTPUPDQBNUYGX-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Imidazopyrimidines |
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| Sub Class | Purines and purine derivatives |
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| Direct Parent | Purines and purine derivatives |
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| Alternative Parents | |
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| Substituents | - Purine
- Hydroxypyrimidine
- Pyrimidine
- Heteroaromatic compound
- Imidazole
- Azole
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | |
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| Disposition | |
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| Process | |
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| Role | |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | 360 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 2.08 mg/mL at 37 °C | Not Available | | LogP | -0.91 | HANSCH,C ET AL. (1995) |
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| Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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| Predicted Molecular Properties | | Show more...
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Guanine,1TMS,isomer #1 | C[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)[NH]1 | 2071.3 | Semi standard non polar | 33892256 | | Guanine,1TMS,isomer #1 | C[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)[NH]1 | 2205.1 | Standard non polar | 33892256 | | Guanine,1TMS,isomer #1 | C[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)[NH]1 | 3244.3 | Standard polar | 33892256 | | Guanine,1TMS,isomer #2 | C[Si](C)(C)N1C(N)=NC(=O)C2=C1N=C[NH]2 | 2010.5 | Semi standard non polar | 33892256 | | Guanine,1TMS,isomer #2 | C[Si](C)(C)N1C(N)=NC(=O)C2=C1N=C[NH]2 | 2100.7 | Standard non polar | 33892256 | | Guanine,1TMS,isomer #2 | C[Si](C)(C)N1C(N)=NC(=O)C2=C1N=C[NH]2 | 3127.8 | Standard polar | 33892256 | | Guanine,1TMS,isomer #3 | C[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)[NH]2 | 2032.3 | Semi standard non polar | 33892256 | | Guanine,1TMS,isomer #3 | C[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)[NH]2 | 2153.7 | Standard non polar | 33892256 | | Guanine,1TMS,isomer #3 | C[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)[NH]2 | 3011.0 | Standard polar | 33892256 | | Guanine,2TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C | 1959.8 | Semi standard non polar | 33892256 | | Guanine,2TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C | 2187.3 | Standard non polar | 33892256 | | Guanine,2TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C | 2981.5 | Standard polar | 33892256 | | Guanine,2TMS,isomer #2 | C[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1 | 2081.3 | Semi standard non polar | 33892256 | | Guanine,2TMS,isomer #2 | C[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1 | 2099.9 | Standard non polar | 33892256 | | Guanine,2TMS,isomer #2 | C[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1 | 2851.8 | Standard polar | 33892256 | | Guanine,2TMS,isomer #3 | C[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C | 1975.7 | Semi standard non polar | 33892256 | | Guanine,2TMS,isomer #3 | C[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C | 2205.9 | Standard non polar | 33892256 | | Guanine,2TMS,isomer #3 | C[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C | 2877.4 | Standard polar | 33892256 | | Guanine,2TMS,isomer #4 | C[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)N2[Si](C)(C)C | 2024.6 | Semi standard non polar | 33892256 | | Guanine,2TMS,isomer #4 | C[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)N2[Si](C)(C)C | 2089.9 | Standard non polar | 33892256 | | Guanine,2TMS,isomer #4 | C[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)N2[Si](C)(C)C | 2809.0 | Standard polar | 33892256 | | Guanine,3TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C | 2045.7 | Semi standard non polar | 33892256 | | Guanine,3TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C | 2145.8 | Standard non polar | 33892256 | | Guanine,3TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C | 2519.8 | Standard polar | 33892256 | | Guanine,3TMS,isomer #2 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C | 2019.1 | Semi standard non polar | 33892256 | | Guanine,3TMS,isomer #2 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C | 2222.9 | Standard non polar | 33892256 | | Guanine,3TMS,isomer #2 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C | 2570.3 | Standard polar | 33892256 | | Guanine,3TMS,isomer #3 | C[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C | 2037.8 | Semi standard non polar | 33892256 | | Guanine,3TMS,isomer #3 | C[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C | 2068.0 | Standard non polar | 33892256 | | Guanine,3TMS,isomer #3 | C[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C | 2592.4 | Standard polar | 33892256 | | Guanine,4TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C | 2092.5 | Semi standard non polar | 33892256 | | Guanine,4TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C | 2175.8 | Standard non polar | 33892256 | | Guanine,4TMS,isomer #1 | C[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C | 2331.7 | Standard polar | 33892256 | | Guanine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)[NH]1 | 2275.7 | Semi standard non polar | 33892256 | | Guanine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)[NH]1 | 2382.2 | Standard non polar | 33892256 | | Guanine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)[NH]1 | 3275.9 | Standard polar | 33892256 | | Guanine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N=C[NH]2 | 2228.9 | Semi standard non polar | 33892256 | | Guanine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N=C[NH]2 | 2299.2 | Standard non polar | 33892256 | | Guanine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N=C[NH]2 | 3127.5 | Standard polar | 33892256 | | Guanine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)[NH]2 | 2292.3 | Semi standard non polar | 33892256 | | Guanine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)[NH]2 | 2338.5 | Standard non polar | 33892256 | | Guanine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)[NH]2 | 3081.3 | Standard polar | 33892256 | | Guanine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C | 2359.4 | Semi standard non polar | 33892256 | | Guanine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C | 2591.4 | Standard non polar | 33892256 | | Guanine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C | 2963.9 | Standard polar | 33892256 | | Guanine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1 | 2477.0 | Semi standard non polar | 33892256 | | Guanine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1 | 2477.7 | Standard non polar | 33892256 | | Guanine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1 | 2903.6 | Standard polar | 33892256 | | Guanine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C | 2398.2 | Semi standard non polar | 33892256 | | Guanine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C | 2576.2 | Standard non polar | 33892256 | | Guanine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C | 2869.6 | Standard polar | 33892256 | | Guanine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C | 2463.5 | Semi standard non polar | 33892256 | | Guanine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C | 2491.7 | Standard non polar | 33892256 | | Guanine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C | 2861.4 | Standard polar | 33892256 | | Guanine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C | 2598.1 | Semi standard non polar | 33892256 | | Guanine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C | 2782.5 | Standard non polar | 33892256 | | Guanine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C | 2701.0 | Standard polar | 33892256 | | Guanine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2555.1 | Semi standard non polar | 33892256 | | Guanine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2813.7 | Standard non polar | 33892256 | | Guanine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2706.5 | Standard polar | 33892256 | | Guanine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C | 2646.2 | Semi standard non polar | 33892256 | | Guanine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C | 2733.0 | Standard non polar | 33892256 | | Guanine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C | 2746.5 | Standard polar | 33892256 | | Guanine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2829.3 | Semi standard non polar | 33892256 | | Guanine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3020.7 | Standard non polar | 33892256 | | Guanine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2673.1 | Standard polar | 33892256 |
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| Spectra |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental GC-MS | GC-MS Spectrum - Guanine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0udi-1938000000-e15e09f2007f35659bb9 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Guanine GC-MS (3 TMS) | splash10-0udi-3739000000-66a080b08ba9b9f82e20 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Guanine EI-B (Non-derivatized) | splash10-0udi-5900000000-0a63148e3a8dc8d026df | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Guanine GC-EI-TOF (Non-derivatized) | splash10-0udi-1938000000-e15e09f2007f35659bb9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Guanine GC-MS (Non-derivatized) | splash10-0udi-3739000000-66a080b08ba9b9f82e20 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Guanine GC-EI-TOF (Non-derivatized) | splash10-0udi-2928000000-073bf70794fe99ce737f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Guanine GC-EI-TOF (Non-derivatized) | splash10-000t-2790000000-77e6b5b71c9ff6ad2b23 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Guanine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ff0-5900000000-f103c75addeafe7ac6f0 | 2016-09-22 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Guanine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0udi-8900000000-699c510cfaf838ab1922 | 2015-03-01 | Not Available | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0udi-0901000000-2864e73c83444d566e9a | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0a4i-2900000000-4229d3d01623054b4ceb | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-000i-0900000000-d5ae84fefadd84f988b4 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-001i-0900000000-7d48b2e8db6967e98407 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0uxr-0900000000-67a7784963ec75cecaa0 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-00di-9000000000-4569516f23d8a712b434 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-001i-0900000000-d928cac1226f19b8edc3 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0udi-0900000000-34059351f2cbd94a8acc | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-0udj-0903100000-deb9c022884d7c98782e | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-001i-0900000000-45d9db80ce4657ef1773 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-004i-1900000000-86b7ee5755cbb8236f5b | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-0udi-0900000000-ba534850b64f39d81fa0 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-0udi-0900000000-422f992621ab9626d1b2 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-0f89-0900000000-64e388178db73f06cb20 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT , negative-QTOF | splash10-0udi-0900000000-f0a95c55947ca990359c | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT , negative-QTOF | splash10-001i-0900000000-45d9db80ce4657ef1773 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-ITFT , negative-QTOF | splash10-0udi-0900000000-ba534850b64f39d81fa0 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine LC-ESI-QTOF , negative-QTOF | splash10-0f89-0900000000-64e388178db73f06cb20 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Guanine , negative-QTOF | splash10-0udi-0900000000-c2e1c1e8841cc741dac1 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Guanine 10V, Positive-QTOF | splash10-0udi-0900000000-e74c005384d71f4787e5 | 2015-05-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Guanine 20V, Positive-QTOF | splash10-0udi-0900000000-de4a4c4479ea93d742b5 | 2015-05-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Guanine 40V, Positive-QTOF | splash10-0a5i-9800000000-da506476184e5c2313a4 | 2015-05-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Guanine 10V, Negative-QTOF | splash10-0udi-0900000000-03d17084c3cb072c0237 | 2015-05-27 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Guanine 20V, Negative-QTOF | splash10-0udi-2900000000-c372e3ba919cba4f561f | 2015-05-27 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Guanine 40V, Negative-QTOF | splash10-00kf-9200000000-8ac435f998deda6437e1 | 2015-05-27 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
|---|
| Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum |
IR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
|---|
| Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Biospecimen Locations | - Blood
- Cellular Cytoplasm
- Feces
- Saliva
- Urine
|
|---|
| Tissue Locations | - Epidermis
- Fibroblasts
- Intestine
- Neuron
- Placenta
- Prostate
- Skeletal Muscle
- Spleen
- Testis
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Cellular Cytoplasm | Detected and Quantified | 97 uM | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Available | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 1.29 +/- 0.68 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected and Quantified | 0.769 +/- 0.404 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected and Quantified | 1.51 +/- 1.37 uM | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 0.20 (0.085-0.26) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | | Urine | Detected and Quantified | 0-4 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.28 (0.17-0.41) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.200 (0.0867-0.267) umol/mmol creatinine | Not Specified | Not Specified | Normal | | details | | Urine | Detected and Quantified | 0.37 (0.18-0.57) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
|---|
| |
| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | | Saliva | Detected and Quantified | 1.36 +/- 0.14 uM | Adult (>18 years old) | Male | Alzheimer's disease | | details | | Saliva | Detected and Quantified | 1.20 +/- 0.33 uM | Adult (>18 years old) | Male | Frontotemporal lobe dementia | | details | | Saliva | Detected and Quantified | 0.93 +/- 0.35 uM | Adult (>18 years old) | Both | Lewy body disease | | details | | Urine | Detected and Quantified | 1.92 (0.99-2.86) umol/mmol creatinine | Not Specified | Both | Lesch-Nyhan syndrome | | details |
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| Associated Disorders and Diseases |
|---|
| Disease References | | Colorectal cancer |
|---|
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| | Alzheimer's disease |
|---|
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| | Frontotemporal dementia |
|---|
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| | Lewy body disease |
|---|
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| | Lesch-Nyhan syndrome |
|---|
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
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| Associated OMIM IDs | |
|---|
| External Links |
|---|
| DrugBank ID | DB02377 |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB004222 |
|---|
| KNApSAcK ID | C00001501 |
|---|
| Chemspider ID | 744 |
|---|
| KEGG Compound ID | C00242 |
|---|
| BioCyc ID | GUANINE |
|---|
| BiGG ID | 34363 |
|---|
| Wikipedia Link | Guanine |
|---|
| METLIN ID | 315 |
|---|
| PubChem Compound | 764 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 16235 |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | GUA |
|---|
| MarkerDB ID | MDB00000063 |
|---|
| Good Scents ID | Not Available |
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| References |
|---|
| Synthesis Reference | Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - Sculley DG, Dawson PA, Emmerson BT, Gordon RB: A review of the molecular basis of hypoxanthine-guanine phosphoribosyltransferase (HPRT) deficiency. Hum Genet. 1992 Nov;90(3):195-207. [PubMed:1487231 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Boulias C, Moscarello MA: Guanine nucleotides stimulate hydrolysis of phosphatidyl inositol bis phosphate in human myelin membranes. Biochem Biophys Res Commun. 1989 Jul 14;162(1):282-7. [PubMed:2546548 ]
- Harkness RA: Hypoxanthine, xanthine and uridine in body fluids, indicators of ATP depletion. J Chromatogr. 1988 Jul 29;429:255-78. [PubMed:3062020 ]
- Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4. [PubMed:7614924 ]
- Steyn LM, Harley EH: Intracellular activity of HPRT Cape Town: purine uptake and growth of cultured cells in selective media. J Inherit Metab Dis. 1985;8(4):198-203. [PubMed:3939543 ]
- Yafe A, Etzioni S, Weisman-Shomer P, Fry M: Formation and properties of hairpin and tetraplex structures of guanine-rich regulatory sequences of muscle-specific genes. Nucleic Acids Res. 2005 May 20;33(9):2887-900. Print 2005. [PubMed:15908587 ]
- Russo TA, Jodush ST, Brown JJ, Johnson JR: Identification of two previously unrecognized genes (guaA and argC) important for uropathogenesis. Mol Microbiol. 1996 Oct;22(2):217-29. [PubMed:8930907 ]
- Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4. [PubMed:7677251 ]
- Parkinson SJ, Waldman SA: An intracellular adenine nucleotide binding site inhibits guanyly cyclase C by a guanine nucleotide-dependent mechanism. Biochemistry. 1996 Mar 12;35(10):3213-21. [PubMed:8605156 ]
- Rodriguez-Nunez A, Camina F, Lojo S, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases and urate in cerebrospinal fluid of children with meningitis. Acta Paediatr. 1993 Oct;82(10):849-52. [PubMed:8241644 ]
- Groopman JD, Zhu JQ, Donahue PR, Pikul A, Zhang LS, Chen JS, Wogan GN: Molecular dosimetry of urinary aflatoxin-DNA adducts in people living in Guangxi Autonomous Region, People's Republic of China. Cancer Res. 1992 Jan 1;52(1):45-52. [PubMed:1727385 ]
- Shioya M, Wakabayashi K, Yamashita K, Nagao M, Sugimura T: Formation of 8-hydroxydeoxyguanosine in DNA treated with fecapentaene-12 and -14. Mutat Res. 1989 Mar;225(3):91-4. [PubMed:2927433 ]
- Allgayer H, Kolb M, Stuber V, Kruis W: Effects of bile acids on base hydroxylation in a model of human colonic mucosal DNA. Cancer Detect Prev. 2002;26(1):85-9. [PubMed:12088208 ]
- Schei MA, Hessen JO, Lund E: House-dust mites and mattresses. Allergy. 2002 Jun;57(6):538-42. [PubMed:12028120 ]
- Weimann A, Belling D, Poulsen HE: Quantification of 8-oxo-guanine and guanine as the nucleobase, nucleoside and deoxynucleoside forms in human urine by high-performance liquid chromatography-electrospray tandem mass spectrometry. Nucleic Acids Res. 2002 Jan 15;30(2):E7. [PubMed:11788733 ]
- Niles JC, Wishnok JS, Tannenbaum SR: Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation. Nitric Oxide. 2006 Mar;14(2):109-21. Epub 2005 Dec 13. [PubMed:16352449 ]
- Spiegel AM: Signal transduction by guanine nucleotide binding proteins. Mol Cell Endocrinol. 1987 Jan;49(1):1-16. [PubMed:2435586 ]
- Fain JN, Wallace MA, Wojcikiewicz RJ: Evidence for involvement of guanine nucleotide-binding regulatory proteins in the activation of phospholipases by hormones. FASEB J. 1988 Jul;2(10):2569-74. [PubMed:2838362 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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