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Showing metabocard for Propionic acid (HMDB0000237)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:03 UTC
HMDB IDHMDB0000237
Secondary Accession Numbers
  • HMDB00237
Metabolite Identification
Common NamePropionic acid
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000237 (Propionic acid)

  Mrv1652305012020142D          

  5  4  0  0  0  0            999 V2000
    1.0718   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
M  END
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3D MOL for HMDB0000237 (Propionic acid)

HMDB0000237
     RDKit          3D
Propionic acid
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.2061    0.4416    0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.4295   -0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -0.5157    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -1.5750    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7435    0.6312    0.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205   -0.2615    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    1.0762   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    1.0658    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582   -1.4426   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -0.0061   -1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060    1.0158   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  5 11  1  0
M  END
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3D SDF for HMDB0000237 (Propionic acid)

  Mrv1652305012020142D          

  5  4  0  0  0  0            999 V2000
    1.0718   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000237

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)

> <INCHI_KEY>
XBDQKXXYIPTUBI-UHFFFAOYSA-N

> <FORMULA>
C3H6O2

> <MOLECULAR_WEIGHT>
74.0785

> <EXACT_MASS>
74.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.24434341571555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propanoic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.47719013266666654

> <ALOGPS_LOGS>
0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7546711681673255

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.2706

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.52e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000237 (Propionic acid)

HMDB0000237
     RDKit          3D
Propionic acid
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.2061    0.4416    0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.4295   -0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -0.5157    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -1.5750    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7435    0.6312    0.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205   -0.2615    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    1.0762   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    1.0658    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582   -1.4426   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -0.0061   -1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060    1.0158   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  5 11  1  0
M  END
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PDB for HMDB0000237 (Propionic acid)

HEADER    PROTEIN                                 01-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-20         0                                  
HETATM    1  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.000  -1.155   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.667   1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0000237 (Propionic acid)

COMPND    HMDB0000237
HETATM    1  C1  UNL     1      -1.206   0.442   0.152  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.164  -0.430  -0.550  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.979  -0.516   0.415  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.192  -1.575   1.013  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.743   0.631   0.577  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.920  -0.262   0.597  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.641   1.076  -0.614  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.761   1.066   0.928  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.558  -1.443  -0.768  1.00  0.00           H  
HETATM   10  H5  UNL     1       0.130  -0.006  -1.528  1.00  0.00           H  
HETATM   11  H6  UNL     1       2.206   1.016  -0.221  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4    4    5
CONECT    5   11
END
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SMILES for HMDB0000237 (Propionic acid)

CCC(O)=O
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INCHI for HMDB0000237 (Propionic acid)

InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Namepropanoic acid
Traditional Namepropanoic acid
CAS Registry Number79-09-4
SMILES
CCC(O)=O
InChI Identifier
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
InChI KeyXBDQKXXYIPTUBI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-20.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.33HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Neuron
  • Platelet
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Propionic acidemia
  1. Thompson GN, Chalmers RA, Walter JH, Bresson JL, Lyonnet SL, Reed PJ, Saudubray JM, Leonard JV, Halliday D: The use of metronidazole in management of methylmalonic and propionic acidaemias. Eur J Pediatr. 1990 Aug;149(11):792-6. [PubMed:2226555 ]
Methylmalonic acidemia
  1. Thompson GN, Chalmers RA, Walter JH, Bresson JL, Lyonnet SL, Reed PJ, Saudubray JM, Leonard JV, Halliday D: The use of metronidazole in management of methylmalonic and propionic acidaemias. Eur J Pediatr. 1990 Aug;149(11):792-6. [PubMed:2226555 ]
Colorectal cancer
  1. Monleon D, Morales JM, Barrasa A, Lopez JA, Vazquez C, Celda B: Metabolite profiling of fecal water extracts from human colorectal cancer. NMR Biomed. 2009 Apr;22(3):342-8. doi: 10.1002/nbm.1345. [PubMed:19006102 ]
  2. Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
  3. Lin Y, Ma C, Liu C, Wang Z, Yang J, Liu X, Shen Z, Wu R: NMR-based fecal metabolomics fingerprinting as predictors of earlier diagnosis in patients with colorectal cancer. Oncotarget. 2016 May 17;7(20):29454-64. doi: 10.18632/oncotarget.8762. [PubMed:27107423 ]
  4. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
  3. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  4. Bjerrum JT, Wang Y, Hao F, Coskun M, Ludwig C, Gunther U, Nielsen OH: Metabonomics of human fecal extracts characterize ulcerative colitis, Crohn's disease and healthy individuals. Metabolomics. 2015;11:122-133. Epub 2014 Jun 1. [PubMed:25598765 ]
  5. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. Bjerrum JT, Wang Y, Hao F, Coskun M, Ludwig C, Gunther U, Nielsen OH: Metabonomics of human fecal extracts characterize ulcerative colitis, Crohn's disease and healthy individuals. Metabolomics. 2015;11:122-133. Epub 2014 Jun 1. [PubMed:25598765 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Rheumatoid arthritis
  1. Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB03766
Phenol Explorer Compound IDNot Available
FooDB IDFDB031132
KNApSAcK IDC00044287
Chemspider ID1005
KEGG Compound IDC00163
BioCyc IDPROPIONATE
BiGG ID34098
Wikipedia LinkPropionic acid
METLIN ID3215
PubChem Compound1032
PDB IDNot Available
ChEBI ID30768
Food Biomarker OntologyNot Available
VMH IDPPA
MarkerDB IDMDB00000115
Good Scents IDNot Available
References
Synthesis ReferenceZhan, Jianghong; Meng, Wei; Gong, Tao; Huang, Fen-sheng. Preparation of propionic acid by propionaldehyde oxidation. Shihua Jishu Yu Yingyong (2005), 23(6), 421-423.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Acetyl-coenzyme A synthetase, cytoplasmic
General function:
Involved in acetate-CoA ligase activity
Specific function:
Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name:
ACSS2
Uniprot ID:
Q9NR19
Molecular weight:
78579.11
Reactions
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylatedetails
Enzyme Details
2. Acetyl-coenzyme A synthetase 2-like, mitochondrial
General function:
Involved in acetate-CoA ligase activity
Specific function:
Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:
ACSS1
Uniprot ID:
Q9NUB1
Molecular weight:
74625.88
Reactions
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylatedetails
Enzyme Details
3. Gephyrin
General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Microtubule-associated protein involved in membrane protein-cytoskeleton interactions. It is thought to anchor the inhibitory glycine receptor (GLYR) to subsynaptic microtubules (By similarity). Catalyzes two steps in the biosynthesis of the molybdenum cofactor. In the first step, molybdopterin is adenylated. Subsequently, molybdate is inserted into adenylated molybdopterin and AMP is released.
Gene Name:
GPHN
Uniprot ID:
Q9NQX3
Molecular weight:
79747.635
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
4. ACSS2 protein
General function:
Involved in acetate-CoA ligase activity
Specific function:
Not Available
Gene Name:
ACSS2
Uniprot ID:
Q96FY7
Molecular weight:
59346.4
Enzyme Details
5. Acyl-CoA synthetase short-chain family member 3, mitochondrial
General function:
Not Available
Specific function:
Activates acetate so that it can be used for lipid synthesis or for energy generation (By similarity).
Gene Name:
ACSS3
Uniprot ID:
Q9H6R3
Molecular weight:
74777.655
Reactions
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylatedetails