Indoleacetic acid

Identification

Name
Indoleacetic acid
Accession Number
DB07950
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (Indol-3-yl)acetate
  • (indol-3-yl)acetic acid
  • 2-(indol-3-yl)ethanoic acid
  • 3-Indolylessigsäure
  • heteroauxin
  • IAA
  • IES
  • Indole-3-acetic acid
Categories
UNII
6U1S09C61L
CAS number
87-51-4
Weight
Average: 175.184
Monoisotopic: 175.063328537
Chemical Formula
C10H9NO2
InChI Key
SEOVTRFCIGRIMH-UHFFFAOYSA-N
InChI
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
IUPAC Name
2-(1H-indol-3-yl)acetic acid
SMILES
OC(=O)CC1=CNC2=CC=CC=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGroup IIE secretory phospholipase A2Not AvailableHuman
US-phase kinase-associated protein 1Not AvailableHuman
UKynurenine--oxoglutarate transaminase 1Not 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
PathwayCategory
Tryptophan MetabolismMetabolic
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000197
KEGG Compound
C00954
PubChem Compound
802
PubChem Substance
99444421
ChemSpider
780
BindingDB
50201883
ChEBI
16411
ChEMBL
CHEMBL82411
HET
IAC
Wikipedia
Indole-3-acetic_acid
PDB Entries
2oyf / 2p1p / 2p1q / 3fvu / 3o97 / 3snm / 4hm0 / 4pgp / 5aog / 5iuw
show 2 more

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.38 mg/mLALOGPS
logP1.87ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.45 m3·mol-1ChemAxon
Polarizability17.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.9852
Caco-2 permeable-0.513
P-glycoprotein substrateNon-substrate0.722
P-glycoprotein inhibitor INon-inhibitor0.9876
P-glycoprotein inhibitor IINon-inhibitor0.9699
Renal organic cation transporterNon-inhibitor0.8884
CYP450 2C9 substrateNon-substrate0.8233
CYP450 2D6 substrateNon-substrate0.8064
CYP450 3A4 substrateNon-substrate0.7535
CYP450 1A2 substrateNon-inhibitor0.8579
CYP450 2C9 inhibitorNon-inhibitor0.912
CYP450 2D6 inhibitorNon-inhibitor0.9426
CYP450 2C19 inhibitorNon-inhibitor0.8916
CYP450 3A4 inhibitorNon-inhibitor0.9593
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9374
Ames testNon AMES toxic0.9519
CarcinogenicityNon-carcinogens0.9318
BiodegradationNot ready biodegradable0.5445
Rat acute toxicity1.9929 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9762
hERG inhibition (predictor II)Non-inhibitor0.9541
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0udi-0391000000-7581f14fe5be5b2b2954
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0udi-0691000000-de9ac4f748d50db109ea
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0udi-0591000000-9687f83d1372abe23c3c
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0udi-1793100000-7c78003038436ec5a902
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-00ai-7910000000-4aa7b8244f32048c76bc
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0fk9-9250000000-a5f931fc3292056dba65
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-001i-1920000000-f0ecee61454a589493af
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0udi-1692000000-ce863a1ca2a657cb41d5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-003r-0900000000-1edcb4977a52155bc130
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0391000000-7581f14fe5be5b2b2954
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0691000000-de9ac4f748d50db109ea
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0591000000-9687f83d1372abe23c3c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-1793100000-7c78003038436ec5a902
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ai-7910000000-4aa7b8244f32048c76bc
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fk9-9250000000-a5f931fc3292056dba65
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-1920000000-f0ecee61454a589493af
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-1692000000-ce863a1ca2a657cb41d5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0691000000-f6073f8f35a6930b5aac
Mass Spectrum (Electron Ionization)MSsplash10-001i-1900000000-3ffc47eb6c977956ad93
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-004i-0900000000-f6dbb01a35af3042d126
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-0900000000-2ae231b7d0e2cd50aed8
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-6900000000-9eae14faa16b8f8259da
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-003r-0900000000-1edcb4977a52155bc130
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-00e9-0900000000-187b48f2258823cbc6a2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-001i-0900000000-30b7a73fa446d0e3c8d3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004i-0900000000-bbe0fb5a48f89ea6e383
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-004i-0900000000-97850f400d80de278334
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-004i-0900000000-600545759ef108827b9e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0kxr-5900000000-ba2eed29832f9ee48921
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-004l-5900000000-a0b30710f83e53b6f3db
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-001i-9500000000-146ac0a20f9d53e76291
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-053r-9600000000-d9258b3c6b5c6f748f6e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004i-9300000000-b59628beb41b424daf4a
LC-MS/MS Spectrum - LC-ESI-QQ (UPLC Waters, Quattro Ultima Pt Micromass) , PositiveLC-MS/MSsplash10-004i-0900000000-755373c9248cfb6425fc
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-004i-0900000000-2b3df7a1dd85faea6705
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-003r-0900000000-9522ab089ab89b64f96a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-b735e95cb23091491c2e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-2a3dd24f136523e6ce1e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0900000000-77436493836245345cb8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-1900000000-4e0b6f24d03c0b25800f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-0900000000-1d045a56f3669a1c9391
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05ai-0900000000-518778c36bacbf77b901
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a5c-3900000000-323fc64084836756be30
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-2a3dd24f136523e6ce1e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0900000000-77436493836245345cb8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-1900000000-4e0b6f24d03c0b25800f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-2a3dd24f136523e6ce1e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0900000000-77436493836245345cb8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-1900000000-4e0b6f24d03c0b25800f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-0900000000-1d045a56f3669a1c9391
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05ai-0900000000-518778c36bacbf77b901
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a5c-3900000000-323fc64084836756be30
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-0900000000-1d045a56f3669a1c9391
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05ai-0900000000-518778c36bacbf77b901
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a5c-3900000000-323fc64084836756be30
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00e9-0900000000-187b48f2258823cbc6a2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-7dd685d97c3fa897c28f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-5e0acffe0e3e18677dbe
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-97850f400d80de278334
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-600545759ef108827b9e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-b735e95cb23091491c2e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-85d7071f8c5d5256e548
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-fbf9b9f81195fcec794d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-8b6d017f531bd8d99040
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fsi-2900000000-be6e948ec5c1c4c29ce3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ufr-8900000000-e75b551fddf1fe5a8a97
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0kxr-5900000000-ba2eed29832f9ee48921
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004l-5900000000-5794fbea4ecd216eeeb8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9600000000-146ac0a20f9d53e76291
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-053r-9600000000-d9258b3c6b5c6f748f6e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-9300000000-b59628beb41b424daf4a
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-001i-0900000000-8f8efcaf5d2147faaa3f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0900000000-c266bea243c4a6a83ca5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-abd6ffb9975b465cf0a3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-003r-0900000000-9522ab089ab89b64f96a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0900000000-45eab4ddd1395448f757
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00or-1900000000-e9cd861052076a748962
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indole-3-acetic acid derivatives
Alternative Parents
3-alkylindoles / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Indole-3-acetic acid derivative / 3-alkylindole / Indole / Substituted pyrrole / Benzenoid / Heteroaromatic compound / Pyrrole / Azacycle / Monocarboxylic acid or derivatives / Carboxylic acid
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid, indole-3-acetic acids (CHEBI:16411) / Indole alkaloids, Auxins (C00954)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name
PLA2G2E
Uniprot ID
Q9NZK7
Uniprot Name
Group IIE secretory phospholipase A2
Molecular Weight
15988.525 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
Ubiquitin-protein transferase activity
Specific Function
Essential component of the SCF (SKP1-CUL1-F-box protein) ubiquitin ligase complex, which mediates the ubiquitination of proteins involved in cell cycle progression, signal transduction and transcri...
Gene Name
SKP1
Uniprot ID
P63208
Uniprot Name
S-phase kinase-associated protein 1
Molecular Weight
18657.86 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
Transaminase activity
Specific Function
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to ...
Gene Name
CCBL1
Uniprot ID
Q16773
Uniprot Name
Kynurenine--oxoglutarate transaminase 1
Molecular Weight
47874.765 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 September 15, 2010 15:27 / Updated on October 01, 2018 14:30