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Showing metabocard for Isobutyric acid (HMDB0001873)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 12:29:19 UTC
Update Date2023-02-21 17:15:53 UTC
HMDB IDHMDB0001873
Secondary Accession Numbers
  • HMDB0003151
  • HMDB01873
  • HMDB03151
Metabolite Identification
Common NameIsobutyric acid
DescriptionIsobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000 ). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001873 (Isobutyric acid)

  Mrv1652303262019152D          

  6  5  0  0  0  0            999 V2000
   -4.4864    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008    0.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719   -0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
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3D MOL for HMDB0001873 (Isobutyric acid)

HMDB0001873
     RDKit          3D
Isobutyric acid
 14 13  0  0  0  0  0  0  0  0999 V2000
   -0.2790    1.2326    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.2385   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.8103   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -0.3754   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -0.2231   -1.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.1073    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.7974    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    2.1877    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.3541    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    0.7661   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.0172    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -1.7558   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -0.3619   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.9254    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
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3D SDF for HMDB0001873 (Isobutyric acid)

  Mrv1652303262019152D          

  6  5  0  0  0  0            999 V2000
   -4.4864    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008    0.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719   -0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001873

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)

> <INCHI_KEY>
KQNPFQTWMSNSAP-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.116588155592677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropanoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
1.020176411

> <ALOGPS_LOGS>
0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.866878196732949

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
21.845100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyric acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001873 (Isobutyric acid)

HMDB0001873
     RDKit          3D
Isobutyric acid
 14 13  0  0  0  0  0  0  0  0999 V2000
   -0.2790    1.2326    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.2385   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.8103   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -0.3754   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -0.2231   -1.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.1073    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.7974    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    2.1877    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.3541    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    0.7661   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.0172    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -1.7558   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -0.3619   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.9254    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
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PDB for HMDB0001873 (Isobutyric acid)

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      -8.375   1.603   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.708   0.833   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -8.375   3.143   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.041   0.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.041  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.707   1.603   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0001873 (Isobutyric acid)

COMPND    HMDB0001873
HETATM    1  C1  UNL     1      -0.279   1.233   0.663  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.144   0.239  -0.467  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.222  -0.810  -0.272  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.202  -0.375  -0.516  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.892  -0.223  -1.555  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.719  -1.107   0.541  1.00  0.00           O  
HETATM    7  H1  UNL     1       0.257   0.797   1.536  1.00  0.00           H  
HETATM    8  H2  UNL     1       0.173   2.188   0.354  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.333   1.354   0.897  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.375   0.766  -1.399  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.406  -1.017   0.812  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.988  -1.756  -0.802  1.00  0.00           H  
HETATM   13  H7  UNL     1      -2.179  -0.362  -0.655  1.00  0.00           H  
HETATM   14  H8  UNL     1       2.683  -0.925   0.861  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11   12   13
CONECT    4    5    5    6
CONECT    6   14
END
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SMILES for HMDB0001873 (Isobutyric acid)

CC(C)C(O)=O
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INCHI for HMDB0001873 (Isobutyric acid)

InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
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Synonyms
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name2-methylpropanoic acid
Traditional Nameisobutyric acid
CAS Registry Number79-31-2
SMILES
CC(C)C(O)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
InChI KeyKQNPFQTWMSNSAP-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
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mL at 20 °CNot Available
LogP0.94SANGSTER (1993)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
  3. Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
  4. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
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 ]
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. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  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 ]
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 ]
Colorectal cancer
  1. 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 ]
  2. 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 ]
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. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  2. 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 ]
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 IDDB02531
Phenol Explorer Compound IDNot Available
FooDB IDFDB003277
KNApSAcK IDC00029462
Chemspider ID6341
KEGG Compound IDC02632
BioCyc IDISOBUTYRATE
BiGG IDNot Available
Wikipedia LinkIsobutyric_acid
METLIN ID106
PubChem Compound6590
PDB IDNot Available
ChEBI ID16135
Food Biomarker OntologyNot Available
VMH IDISOBUT
MarkerDB IDMDB00000349
Good Scents IDNot Available
References
Synthesis ReferenceWang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  2. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. [PubMed:6740214 ]
  3. Mix KS, Coon CI, Rosen ED, Suh N, Sporn MB, Brinckerhoff CE: Peroxisome proliferator-activated receptor-gamma-independent repression of collagenase gene expression by 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and prostaglandin 15-deoxy-delta(12,14) J2: a role for Smad signaling. Mol Pharmacol. 2004 Feb;65(2):309-18. [PubMed:14742672 ]
  4. Faed EM, McQueen EG: Separation of two conjugates of clofibric acid (CPIB) found in the urine of subjects taking clofibrate. Clin Exp Pharmacol Physiol. 1978 Mar-Apr;5(2):195-8. [PubMed:648038 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Isobutyric acid → 3,4,5-trihydroxy-6-[(2-methylpropanoyl)oxy]oxane-2-carboxylic aciddetails