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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:51 UTC
HMDB IDHMDB0000734
Secondary Accession Numbers
  • HMDB00734
Metabolite Identification
Common NameIndoleacrylic acid
DescriptionIndoleacrylic acid (CAS: 1204-06-4), also known as indoleacrylate, IA, and IAcrA, is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indoleacrylic acid is practically insoluble (in water) and a weak acidic compound (based on its pKa). Within the cell, indoleacrylic acid is primarily located in the membrane (predicted from logP). Indoleacrylic acid is best known as a plant growth hormone (a natural auxin), whereas its biological role in animals is still unknown. A two-stage production of this compound is likely: intestinal microorganisms catabolize tryptophan to indole derivatives which are then absorbed and converted into indoleacrylic acid and its glycine conjugate, indolylacryloylglycine (IAcrGly). Indolylacryloylglycine excretion in urine is especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy (PMID: 10707769 ). It has been recently found that indoleacrylic acid promotes intestinal epithelial barrier function and mitigates inflammatory responses. Stimulating indoleacrylic acid production could promote anti-inflammatory responses and have therapeutic benefits (PMID: 28704649 ). Urinary Indole-3-acrylate is produced by Clostridium sporogenes (PMID: 29168502 ). Indoleacrylic acid is also a metabolite of Peptostreptococcus (PMID: 28704649 , 29168502 ).
Structure
Data?1582752153
Synonyms
ValueSource
3-(3-Indolyl)acrylic acidChEBI
3-Indoleacrylic acidChEBI
3-Indolylacrylic acidChEBI
Indole-3-acrylic acidChEBI
Indole-3beta-acrylic acidChEBI
Indoleacrylic acidChEBI
trans-3-Indoleacrylic acidChEBI
trans-beta-Indoleacrylic acidChEBI
3-(3-Indolyl)acrylateGenerator
3-IndoleacrylateGenerator
3-IndolylacrylateGenerator
Indole-3-acrylateGenerator
Indole-3b-acrylateGenerator
Indole-3b-acrylic acidGenerator
Indole-3beta-acrylateGenerator
Indole-3β-acrylateGenerator
Indole-3β-acrylic acidGenerator
IndoleacrylateGenerator
trans-3-IndoleacrylateGenerator
trans-b-IndoleacrylateGenerator
trans-b-Indoleacrylic acidGenerator
trans-beta-IndoleacrylateGenerator
trans-Β-indoleacrylateGenerator
trans-Β-indoleacrylic acidGenerator
(e)-3-(indol-3-yl)AcrylateGenerator
Indoleacrylic acid, (e)-isomerMeSH
Indoleacrylic acid, sodium saltMeSH
Indole acrylic acidMeSH
(2E)-3-(1H-Indol-3-yl)-2-propenoic acidHMDB
(E)-3-(1H-Indol-3-yl)-2-propenoic acidHMDB
(E)-3-(1H-Indol-3-yl)prop-2-enoic acidHMDB
(E)-Indole-3-acrylic acidHMDB
3-(1H-Indol-3-yl)-2-propenoic acidHMDB
3-(1H-Indol-3-yl)acrylic acidHMDB
3-(Indol-3-yl)prop-2-enoic acidHMDB
3-beta-Indoleacrylic acidHMDB
3-β-Indoleacrylic acidHMDB
IAHMDB
IAcrAHMDB
Chemical FormulaC11H9NO2
Average Molecular Weight187.198
Monoisotopic Molecular Weight187.063328534
IUPAC Name(2E)-3-(1H-indol-3-yl)prop-2-enoic acid
Traditional Name(2E)-3-(1H-indol-3-yl)prop-2-enoic acid
CAS Registry Number29953-71-7
SMILES
OC(=O)\C=C\C1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
InChI KeyPLVPPLCLBIEYEA-AATRIKPKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 - 186 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.29ALOGPS
logP2.23ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.15 m³·mol⁻¹ChemAxon
Polarizability19.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000938
KNApSAcK IDNot Available
Chemspider ID4524636
KEGG Compound IDNot Available
BioCyc IDCPD-11578
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5375048
PDB IDNot Available
ChEBI ID132244
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMoffatt, J. S. Preparation of b-3-indolylacrylic acid. Journal of the Chemical Society (1957), 1442-3.; Bauguess, Lyle C.; Berg, Clarence P. The availability of indole derivatives for supplementing diets deficient in tryptophan. Proceedings of the Iowa Academy of Science (1933), 40 110-11.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13. [PubMed:10707769 ]
  2. Wlodarska M, Luo C, Kolde R, d'Hennezel E, Annand JW, Heim CE, Krastel P, Schmitt EK, Omar AS, Creasey EA, Garner AL, Mohammadi S, O'Connell DJ, Abubucker S, Arthur TD, Franzosa EA, Huttenhower C, Murphy LO, Haiser HJ, Vlamakis H, Porter JA, Xavier RJ: Indoleacrylic Acid Produced by Commensal Peptostreptococcus Species Suppresses Inflammation. Cell Host Microbe. 2017 Jul 12;22(1):25-37.e6. doi: 10.1016/j.chom.2017.06.007. [PubMed:28704649 ]
  3. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]