3-Indolebutyric Acid

Identification

Name
3-Indolebutyric Acid
Accession Number
DB02740  (EXPT00173)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-3130
Categories
Not Available
UNII
061SKE27JP
CAS number
133-32-4
Weight
Average: 203.2371
Monoisotopic: 203.094628665
Chemical Formula
C12H13NO2
InChI Key
JTEDVYBZBROSJT-UHFFFAOYSA-N
InChI
InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)
IUPAC Name
4-(1H-indol-3-yl)butanoic acid
SMILES
OC(=O)CCCC1=CNC2=C1C=CC=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAromatic-amino-acid aminotransferaseNot AvailableParacoccus denitrificans
UBeta-2-microglobulinNot AvailableHuman
UT-cell receptor alpha chain C regionNot AvailableHuman
UT-cell receptor beta-1 chain C regionNot AvailableHuman
UHLA class I histocompatibility antigen, A-2 alpha chainNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB02096
KEGG Compound
C11284
PubChem Compound
8617
PubChem Substance
46505244
ChemSpider
8298
BindingDB
50129081
ChEBI
33070
ChEMBL
CHEMBL582878
HET
3IB
PDB Entries
2ay6 / 2gj6

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)124.5 °CPhysProp
water solubility250 mg/L (at 20 °C)TOMLIN,C (1994)
logP2.30HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.356 mg/mLALOGPS
logP2.38ALOGPS
logP2.6ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.65 m3·mol-1ChemAxon
Polarizability22.03 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9934
Blood Brain Barrier+0.9789
Caco-2 permeable-0.5427
P-glycoprotein substrateNon-substrate0.7023
P-glycoprotein inhibitor INon-inhibitor0.9863
P-glycoprotein inhibitor IINon-inhibitor0.9534
Renal organic cation transporterNon-inhibitor0.8472
CYP450 2C9 substrateNon-substrate0.8162
CYP450 2D6 substrateNon-substrate0.8075
CYP450 3A4 substrateNon-substrate0.7305
CYP450 1A2 substrateNon-inhibitor0.7261
CYP450 2C9 inhibitorNon-inhibitor0.8397
CYP450 2D6 inhibitorNon-inhibitor0.947
CYP450 2C19 inhibitorNon-inhibitor0.8916
CYP450 3A4 inhibitorNon-inhibitor0.9402
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9181
Ames testNon AMES toxic0.9559
CarcinogenicityNon-carcinogens0.9566
BiodegradationReady biodegradable0.5241
Rat acute toxicity2.0347 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9491
hERG inhibition (predictor II)Non-inhibitor0.9446
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-000x-0910000000-7c2b4d74ecedb117caf3
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0udi-0391000000-c62444bc1faa5f67d652
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-0920000000-a53e6a97ea38d50751b7
GC-MS Spectrum - GC-MSGC-MSsplash10-000x-0910000000-7c2b4d74ecedb117caf3
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-0391000000-c62444bc1faa5f67d652
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0f79-0970000000-7543d99fe8a1f2b0de25
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00lu-0900000000-b46d8f64c372b7348dbd
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00lu-2900000000-ccb02800c683b0a921ee
MS/MS Spectrum - EI-B (HITACHI M-68) , PositiveLC-MS/MSsplash10-001i-0920000000-a53e6a97ea38d50751b7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0udi-0090000000-d6f784c6fec287fbd7c4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0udi-0590000000-22d2baa6bbf6262cb3cf
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014i-1900000000-21352951c1447c77df39
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014i-2900000000-184013bb3b879000bdf1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-014i-2900000000-cd1951f573aa0d883a8c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0f79-1930000000-d04d53f6788d45ef881f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-002u-2900000000-e52b6e60b86d650a9c2e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0032-8900000000-f17437c2c96f7f7f4ed2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-017j-9500000000-8e79159a3b4ebf3488d8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-5900000000-afb8479ad9268699e823
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0090000000-d6f784c6fec287fbd7c4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0590000000-22d2baa6bbf6262cb3cf
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-1900000000-21352951c1447c77df39
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-2900000000-184013bb3b879000bdf1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-2900000000-cd1951f573aa0d883a8c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0f79-1930000000-d04d53f6788d45ef881f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-002u-2900000000-e52b6e60b86d650a9c2e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0032-8900000000-f17437c2c96f7f7f4ed2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-017j-9500000000-8e79159a3b4ebf3488d8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-5900000000-afb8479ad9268699e823
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
3-alkylindole / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Azacycle / Organic oxygen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indol-3-yl carboxylic acid (CHEBI:33070)

Targets

Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Shows activities toward both dicarboxylic and aromatic substrates.
Gene Name
tyrB
Uniprot ID
P95468
Uniprot Name
Aromatic-amino-acid aminotransferase
Molecular Weight
42731.635 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Component of the class I major histocompatibility complex (MHC). Involved in the presentation of peptide antigens to the immune system.
Gene Name
B2M
Uniprot ID
P61769
Uniprot Name
Beta-2-microglobulin
Molecular Weight
13714.43 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
TRAC
Uniprot ID
P01848
Uniprot Name
T-cell receptor alpha chain C region
Molecular Weight
15927.645 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
TRBC1
Uniprot ID
P01850
Uniprot Name
T-cell receptor beta-1 chain C region
Molecular Weight
19898.43 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tap binding
Specific Function
Involved in the presentation of foreign antigens to the immune system.
Gene Name
HLA-A
Uniprot ID
P01892
Uniprot Name
HLA class I histocompatibility antigen, A-2 alpha chain
Molecular Weight
40921.59 Da
References
  1. 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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:18