Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:07 UTC

HMDB ID

HMDB0000734

Secondary Accession Numbers

HMDB00734

Metabolite Identification

Common Name

Indoleacrylic acid

Description

Indoleacrylic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304202022142D          

 14 15  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0468 9999.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3323 9998.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000734

> <DATABASE_NAME>
hmdb

> <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_KEY>
PLVPPLCLBIEYEA-AATRIKPKSA-N

> <FORMULA>
C11H9NO2

> <MOLECULAR_WEIGHT>
187.198

> <EXACT_MASS>
187.063328534

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.34464224554396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(1H-indol-3-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.234848253

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.393868468603337

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650101023193603

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
54.146400000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(1H-indol-3-yl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8670.4878665.395   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8669.1548663.085   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8669.1548664.625   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8    5                                                       
CONECT   10   12                                                            
CONECT   11   12                                                            
CONECT   12   10   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(3-Indolyl)acrylic acid	ChEBI
3-Indoleacrylic acid	ChEBI
3-Indolylacrylic acid	ChEBI
Indole-3-acrylic acid	ChEBI
Indole-3beta-acrylic acid	ChEBI
trans-3-Indoleacrylic acid	ChEBI
trans-beta-Indoleacrylic acid	ChEBI
3-(3-Indolyl)acrylate	Generator
3-Indoleacrylate	Generator
3-Indolylacrylate	Generator
Indole-3-acrylate	Generator
Indole-3b-acrylate	Generator
Indole-3b-acrylic acid	Generator
Indole-3beta-acrylate	Generator
Indole-3β-acrylate	Generator
Indole-3β-acrylic acid	Generator
trans-3-Indoleacrylate	Generator
trans-b-Indoleacrylate	Generator
trans-b-Indoleacrylic acid	Generator
trans-beta-Indoleacrylate	Generator
trans-Β-indoleacrylate	Generator
trans-Β-indoleacrylic acid	Generator
Indoleacrylate	Generator
(e)-3-(indol-3-yl)Acrylate	HMDB
Indoleacrylic acid, (e)-isomer	HMDB
Indoleacrylic acid, sodium salt	HMDB
Indole acrylic acid	HMDB
(2E)-3-(1H-indol-3-yl)-2-Propenoic acid	HMDB
(e)-3-(1H-indol-3-yl)-2-Propenoic acid	HMDB
(e)-3-(1H-indol-3-yl)Prop-2-enoic acid	HMDB
(e)-Indole-3-acrylic acid	HMDB
3-(1H-indol-3-yl)-2-Propenoic acid	HMDB
3-(1H-indol-3-yl)Acrylic acid	HMDB
3-(indol-3-yl)Prop-2-enoic acid	HMDB
3-beta-Indoleacrylic acid	HMDB
3-Β-indoleacrylic acid	HMDB
IA	HMDB
IAcrA	HMDB
Indoleacrylic acid	ChEBI

Chemical Formula

C₁₁H₉NO₂

Average Molecular Weight

187.198

Monoisotopic Molecular Weight

187.063328534

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 Number

29953-71-7

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 Key

PLVPPLCLBIEYEA-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0000734)

Source

Exogenous

Exogenous (HMDB: HMDB0000734)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000734)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 - 186 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	134.534	30932474
[M-H]-	Not Available	134.534	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000329

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.23	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.15 m³·mol⁻¹	ChemAxon
Polarizability	19.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	137.085	30932474
DeepCCS	[M-H]-	134.689	30932474
DeepCCS	[M-2H]-	169.536	30932474
DeepCCS	[M+Na]+	143.995	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	144.4	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	140.5	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	140.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indoleacrylic acid	OC(=O)\C=C\C1=CNC2=C1C=CC=C2	3270.3	Standard polar	33892256
Indoleacrylic acid	OC(=O)\C=C\C1=CNC2=C1C=CC=C2	2105.2	Standard non polar	33892256
Indoleacrylic acid	OC(=O)\C=C\C1=CNC2=C1C=CC=C2	2194.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indoleacrylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=C[NH]C2=CC=CC=C12	2232.4	Semi standard non polar	33892256
Indoleacrylic acid,1TMS,isomer #2	C[Si](C)(C)N1C=C(/C=C/C(=O)O)C2=CC=CC=C21	2350.6	Semi standard non polar	33892256
Indoleacrylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12	2410.3	Semi standard non polar	33892256
Indoleacrylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12	2298.3	Standard non polar	33892256
Indoleacrylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12	2288.4	Standard polar	33892256
Indoleacrylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=C[NH]C2=CC=CC=C12	2506.1	Semi standard non polar	33892256
Indoleacrylic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(/C=C/C(=O)O)C2=CC=CC=C21	2599.5	Semi standard non polar	33892256
Indoleacrylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2812.7	Semi standard non polar	33892256
Indoleacrylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2673.4	Standard non polar	33892256
Indoleacrylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2502.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indoleacrylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoleacrylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoleacrylic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoleacrylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoleacrylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 20V, Positive-QTOF	splash10-00xu-1900000000-b9703e40501d9e8edb5e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 30V, Positive-QTOF	splash10-014i-1900000000-b61bd7aa8af6bfffb9fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 40V, Positive-QTOF	splash10-014i-2900000000-4f6e782714d62002ea7d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 30V, Positive-QTOF	splash10-014i-3900000000-7d161a840c2433ba3cc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 10V, Positive-QTOF	splash10-00di-1900000000-f0c356eafe61b0cff315	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 10V, Positive-QTOF	splash10-00di-0900000000-60502017fa96aaf92805	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indoleacrylic acid 0V, Positive-QTOF	splash10-00dr-0900000000-1a63e095eac9d096de2f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoleacrylic acid 10V, Negative-QTOF	splash10-000f-0900000000-63452d36e3479aca369b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoleacrylic acid 20V, Negative-QTOF	splash10-0006-0900000000-23c0ffcf30e93321ff26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoleacrylic acid 40V, Negative-QTOF	splash10-0006-0900000000-bd668265f9ca314a1b22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoleacrylic acid 10V, Positive-QTOF	splash10-0079-0900000000-ea25947744f2eae98bd0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoleacrylic acid 20V, Positive-QTOF	splash10-002f-0900000000-1d783e0bac13d081e15b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoleacrylic acid 40V, Positive-QTOF	splash10-00mo-3900000000-e7f6eb25881f509bdd0b	2021-09-22	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

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112378

KNApSAcK ID

Not Available

Chemspider ID

4524636

KEGG Compound ID

Not Available

BioCyc ID

CPD-11578

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5375048

PDB ID

Not Available

ChEBI ID

132244

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Moffatt, 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)

Not Available

General References

Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13. [PubMed:10707769 ]
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 ]
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 ]

Showing metabocard for Indoleacrylic acid (HMDB0000734)

MOL for HMDB0000734 (Indoleacrylic acid)

3D MOL for HMDB0000734 (Indoleacrylic acid)

3D SDF for HMDB0000734 (Indoleacrylic acid)

3D-SDF for HMDB0000734 (Indoleacrylic acid)

PDB for HMDB0000734 (Indoleacrylic acid)

3D PDB for HMDB0000734 (Indoleacrylic acid)

SMILES for HMDB0000734 (Indoleacrylic acid)

INCHI for HMDB0000734 (Indoleacrylic acid)

Structure for HMDB0000734 (Indoleacrylic acid)

3D Structure for HMDB0000734 (Indoleacrylic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra