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 | 2021-09-14 15:45:02 UTC |
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HMDB ID | HMDB0001036 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Angiotensin III |
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Description | Angiotensin III (AngIII) is one of the N-terminal angiotensin degradation products of angiotensin II. AngIII shares some of its properties with Ang II, including chemotaxis and production of growth factors and chemokines. AngIII generated within the brain acts within neural circuits of the central nervous system to regulate body fluid balance. The stimulation of vasopressin release by AngIII is thought to be one of the mechanisms by which AngIII controls volume homeostasis under conditions of hypovolemia, by reducing renal water loss and increasing blood pressure. Brain aminopeptidase A, the enzyme forming central AngIII, could constitute a putative central therapeutic target for the treatment of hypertension. (PMID: 17210474 , 11751722 , 11295571 ). |
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Structure | CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCN=C(N)N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O InChI=1S/C46H66N12O9/c1-5-27(4)38(57-40(61)33(21-29-15-17-31(59)18-16-29)53-42(63)37(26(2)3)56-39(60)32(47)13-9-19-51-46(48)49)43(64)54-34(23-30-24-50-25-52-30)44(65)58-20-10-14-36(58)41(62)55-35(45(66)67)22-28-11-7-6-8-12-28/h6-8,11-12,15-18,24-27,32-38,59H,5,9-10,13-14,19-23,47H2,1-4H3,(H,50,52)(H,53,63)(H,54,64)(H,55,62)(H,56,60)(H,57,61)(H,66,67)(H4,48,49,51)/t27-,32-,33-,34-,35-,36-,37-,38-/m0/s1 |
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Synonyms | Value | Source |
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Des-asp-1-angiotensin II | HMDB | Angiotensin II, des-asp | MeSH, HMDB | Des asp angiotensin II | MeSH, HMDB | Des aspartyl angiotensin II | MeSH, HMDB | Des-asp angiotensin II | MeSH, HMDB | Des-aspartyl-angiotensin II | MeSH, HMDB | (2S)-2-({[(2S)-1-[(2S)-2-{[(2S,3S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoate | Generator, HMDB | Angiotensin III | MeSH |
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Chemical Formula | C46H66N12O9 |
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Average Molecular Weight | 931.0912 |
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Monoisotopic Molecular Weight | 930.50757177 |
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IUPAC Name | (2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid |
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Traditional Name | (2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(3H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid |
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CAS Registry Number | 12687-51-3 |
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SMILES | CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCN=C(N)N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C46H66N12O9/c1-5-27(4)38(57-40(61)33(21-29-15-17-31(59)18-16-29)53-42(63)37(26(2)3)56-39(60)32(47)13-9-19-51-46(48)49)43(64)54-34(23-30-24-50-25-52-30)44(65)58-20-10-14-36(58)41(62)55-35(45(66)67)22-28-11-7-6-8-12-28/h6-8,11-12,15-18,24-27,32-38,59H,5,9-10,13-14,19-23,47H2,1-4H3,(H,50,52)(H,53,63)(H,54,64)(H,55,62)(H,56,60)(H,57,61)(H,66,67)(H4,48,49,51)/t27-,32-,33-,34-,35-,36-,37-,38-/m0/s1 |
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InChI Key | QMMRCKSBBNJCMR-KMZPNFOHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Oligopeptides |
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Alternative Parents | |
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Substituents | - Alpha-oligopeptide
- Tyrosine or derivatives
- Phenylalanine or derivatives
- Histidine or derivatives
- Isoleucine or derivatives
- N-acyl-alpha-amino acid
- Valine or derivatives
- Proline or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- Alpha-amino acid amide
- 3-phenylpropanoic-acid
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Amphetamine or derivatives
- Imidazolyl carboxylic acid derivative
- N-acylpyrrolidine
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine-2-carboxamide
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Fatty amide
- N-acyl-amine
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Heteroaromatic compound
- Tertiary carboxylic acid amide
- Pyrrolidine
- Imidazole
- Azole
- Carboxamide group
- Secondary carboxylic acid amide
- Guanidine
- Amino acid
- Amino acid or derivatives
- Azacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Carboximidamide
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboxylic acid
- Amine
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organic oxide
- Organonitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Primary amine
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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Spectra |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 10V, Positive-QTOF | splash10-06vi-5961232228-ea4adf55f419bbf3e0a8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 20V, Positive-QTOF | splash10-0200-6921010000-78b0faf8ce8050666bf0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 40V, Positive-QTOF | splash10-0209-9410000000-bbebe48db6281a886339 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 10V, Negative-QTOF | splash10-000i-1000000092-4a7a50dd8f3ff61c013e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 20V, Negative-QTOF | splash10-08fr-7312022291-47ca9d35823f8d125113 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 40V, Negative-QTOF | splash10-08fu-9232011110-c5464e972b484b1210fe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 10V, Negative-QTOF | splash10-004i-0000100009-cb682999fd045f9fc4d9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 20V, Negative-QTOF | splash10-03kc-5295211253-96684706f7b52c76d77e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 40V, Negative-QTOF | splash10-03kd-6648180390-5726793f99bc63ef5611 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 10V, Positive-QTOF | splash10-001i-0223330329-7bdcba8cf45b54090ccb | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 20V, Positive-QTOF | splash10-06tr-3922011002-e608edceb9299f7d9e64 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Angiotensin III 40V, Positive-QTOF | splash10-00dr-9500012201-3a78900784d621a6a389 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.0000215 +/- 0.0000022 uM | Adult (>18 years old) | Both | Hypertension | | details |
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Associated Disorders and Diseases |
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Disease References | Hypertension |
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- Sim MK, Qui XS: Angiotensins in plasma of hypertensive rats and human. Regul Pept. 2003 Mar 28;111(1-3):179-82. [PubMed:12609766 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022384 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2339529 |
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KEGG Compound ID | C15848 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Angiotensin |
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METLIN ID | Not Available |
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PubChem Compound | 3082042 |
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PDB ID | Not Available |
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ChEBI ID | 1183270 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Arita M, Wanaka Y: [Angiotensin I, angiotensin II, angiotensin III]. Nihon Rinsho. 1999 Dec;57 Suppl:382-5. [PubMed:10778144 ]
- Ruiz-Ortega M, Lorenzo O, Ruperez M, Esteban V, Suzuki Y, Mezzano S, Plaza JJ, Egido J: Role of the renin-angiotensin system in vascular diseases: expanding the field. Hypertension. 2001 Dec 1;38(6):1382-7. [PubMed:11751722 ]
- Llorens-Cortes C, Mendelsohn FA: Organisation and functional role of the brain angiotensin system. J Renin Angiotensin Aldosterone Syst. 2002 Sep;3 Suppl 1:S39-48. [PubMed:12428219 ]
- Vauquelin G, Michotte Y, Smolders I, Sarre S, Ebinger G, Dupont A, Vanderheyden P: Cellular targets for angiotensin II fragments: pharmacological and molecular evidence. J Renin Angiotensin Aldosterone Syst. 2002 Dec;3(4):195-204. [PubMed:12584663 ]
- Haulica I, Petrescu G, Slatineanu SM, Bild W, Mihaila CN, Ionita T: New bioactive angiotensins formation pathways and functional involvements. Rom J Intern Med. 2004;42(1):27-40. [PubMed:15529593 ]
- Reaux-Le Goazigo A, Iturrioz X, Fassot C, Claperon C, Roques BP, Llorens-Cortes C: Role of angiotensin III in hypertension. Curr Hypertens Rep. 2005 Apr;7(2):128-34. [PubMed:15748538 ]
- Nomura S, Ito T, Yamamoto E, Sumigama S, Iwase A, Okada M, Shibata K, Ando H, Ino K, Kikkawa F, Mizutani S: Gene regulation and physiological function of placental leucine aminopeptidase/oxytocinase during pregnancy. Biochim Biophys Acta. 2005 Aug 1;1751(1):19-25. [PubMed:15894523 ]
- Martinez-Martos JM, Ramirez-Exposito MJ: Dietary fat and hypertension: a novel approach through the proteolytic regulatory enzymes of the renin-angiotensin-system. Cardiovasc Hematol Agents Med Chem. 2006 Jul;4(3):263-76. [PubMed:16842210 ]
- Banegas I, Prieto I, Vives F, Alba F, de Gasparo M, Segarra AB, Hermoso F, Duran R, Ramirez M: Brain aminopeptidases and hypertension. J Renin Angiotensin Aldosterone Syst. 2006 Sep;7(3):129-34. [PubMed:17094048 ]
- Skeggs LT, Dorer FE, Kahn JR, Lentz KE, Levine M: The biochemistry of the renin-angiotensin system and its role in hypertension. Am J Med. 1976 May 31;60(6):737-48. [PubMed:190880 ]
- Hanley MR, Cheung WT, Hawkins P, Poyner D, Benton HP, Blair L, Jackson TR, Goedert M: The mas oncogene as a neural peptide receptor: expression, regulation and mechanism of action. Ciba Found Symp. 1990;150:23-38; discussion 38-46. [PubMed:2197067 ]
- Symonds EM: Renin and reproduction. Am J Obstet Gynecol. 1988 Apr;158(4):754-61. [PubMed:3284361 ]
- Levens NR: Control of intestinal absorption by the renin-angiotensin system. Am J Physiol. 1985 Jul;249(1 Pt 1):G3-15. [PubMed:3893156 ]
- Dimitrov T: [Renin-angiotensin system blockers]. Eksp Med Morfol. 1982;21(2):49-54. [PubMed:6183092 ]
- Stokes GS: The renin angiotensin system--its physiology and role in disease states. Anaesth Intensive Care. 1983 Nov;11(4):369-76. [PubMed:6316802 ]
- Ganong WF: The brain renin-angiotensin system. Annu Rev Physiol. 1984;46:17-31. [PubMed:6324655 ]
- Smith RD, Timmermans PB: Human angiotensin receptor subtypes. Curr Opin Nephrol Hypertens. 1994 Jan;3(1):112-22. [PubMed:7850406 ]
- Wright JW, Harding JW: Brain angiotensin receptor subtypes in the control of physiological and behavioral responses. Neurosci Biobehav Rev. 1994 Spring;18(1):21-53. [PubMed:8170622 ]
- Wada N, Kubo M, Kijima H, Yamane Y, Nishikawa T, Sasano H, Koike T: A case of deoxycorticosterone-producing adrenal adenoma. Endocr J. 1995 Oct;42(5):637-42. [PubMed:8574286 ]
- Mosimann R, Imboden H, Felix D: The neuronal role of angiotensin II in thirst, sodium appetite, cognition and memory. Biol Rev Camb Philos Soc. 1996 Nov;71(4):545-59. [PubMed:8923799 ]
- Wright JW, Harding JW: Important role for angiotensin III and IV in the brain renin-angiotensin system. Brain Res Brain Res Rev. 1997 Sep 30;25(1):96-124. [PubMed:9370053 ]
- Dimitrov Y, Muller S, Hannedouche T: [Renal effects of AT1 angiotensin receptor antagonists (AT1ra)]. Presse Med. 1997 Dec 20;26(40):1981-6. [PubMed:9537002 ]
- Moeller I, Allen AM, Chai SY, Zhuo J, Mendelsohn FA: Bioactive angiotensin peptides. J Hum Hypertens. 1998 May;12(5):289-93. [PubMed:9655649 ]
- Chansel D, Ardaillou R: [Active metabolites derived from angiotensin II]. Nephrologie. 1998;19(7):427-32. [PubMed:9857379 ]
- Gard PR: Angiotensin as a target for the treatment of Alzheimer's disease, anxiety and depression. Expert Opin Ther Targets. 2004 Feb;8(1):7-14. [PubMed:14996614 ]
- Arita M: [Angiotensin I, angiotensin II, angiotensin III]. Nihon Rinsho. 2005 Aug;63 Suppl 8:564-7. [PubMed:16149578 ]
- Kono T: [Diagnostic tests for endocrine hypertension]. Rinsho Byori. 1984 Jan;Spec No 58:144-55. [PubMed:6088844 ]
- Ruiz-Ortega M, Esteban V, Egido J: The regulation of the inflammatory response through nuclear factor-kappab pathway by angiotensin IV extends the role of the renin angiotensin system in cardiovascular diseases. Trends Cardiovasc Med. 2007 Jan;17(1):19-25. [PubMed:17210474 ]
- Reaux A, Fournie-Zaluski MC, Llorens-Cortes C: Angiotensin III: a central regulator of vasopressin release and blood pressure. Trends Endocrinol Metab. 2001 May-Jun;12(4):157-62. [PubMed:11295571 ]
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