3-Indolebutyric Acid

Identification

Generic Name
3-Indolebutyric Acid
DrugBank Accession Number
DB02740
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 203.2371
Monoisotopic: 203.094628665
Chemical Formula
C12H13NO2
Synonyms
Not Available
External IDs
  • NSC-3130

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAromatic-amino-acid aminotransferaseNot AvailableParacoccus denitrificans
UBeta-2-microglobulinNot AvailableHumans
UT-cell receptor alpha chain C regionNot AvailableHumans
UT-cell receptor beta-1 chain C regionNot AvailableHumans
UHLA class I histocompatibility antigen, A-2 alpha chainNot AvailableHumans
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

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indol-3-yl carboxylic acid (CHEBI:33070)
Affected organisms
Not Available

Chemical Identifiers

UNII
061SKE27JP
CAS number
133-32-4
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

References

General References
Not Available
Human Metabolome Database
HMDB0002096
KEGG Compound
C11284
PubChem Compound
8617
PubChem Substance
46505244
ChemSpider
8298
BindingDB
50129081
ChEBI
33070
ChEMBL
CHEMBL582878
ZINC
ZINC000000057378
PDBe Ligand
3IB
PDB Entries
2ay6 / 2gj6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

Drugtargets
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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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
5. HLA class I histocompatibility antigen, A-2 alpha chain
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. [Article]

Drug created on June 13, 2005 13:24 / Updated on August 01, 2020 13:46