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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 09:24:25 UTC
Update Date2021-09-24 09:24:25 UTC
HMDB IDHMDB0304388
Secondary Accession NumbersNone
Metabolite Identification
Common Nameindole-3-acetyl-tyrosine
Description4-(2-carboxy-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}ethyl)benzen-1-olate belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on 4-(2-carboxy-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}ethyl)benzen-1-olate.
Structure
Thumb
Synonyms
ValueSource
4-(2-Carboxy-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}ethyl)benzen-1-olic acidGenerator
Indole-3-acetyl-tyrMetaCyc
IAA-tyrMetaCyc
Chemical FormulaC19H17N2O4
Average Molecular Weight337.356
Monoisotopic Molecular Weight337.119380615
IUPAC Name3-(4-hydroxyphenyl)-2-[2-(1H-indol-3-yl)acetamido]propanoate
Traditional Name3-(4-hydroxyphenyl)-2-[2-(1H-indol-3-yl)acetamido]propanoate
CAS Registry NumberNot Available
SMILES
OC1=CC=C(CC(NC(=O)CC2=CNC3=C2C=CC=C3)C([O-])=O)C=C1
InChI Identifier
InChI=1S/C19H18N2O4/c22-14-7-5-12(6-8-14)9-17(19(24)25)21-18(23)10-13-11-20-16-4-2-1-3-15(13)16/h1-8,11,17,20,22H,9-10H2,(H,21,23)(H,24,25)/p-1
InChI KeyHLBLLQMXYYYBLN-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.23ALOGPS
logP2.53ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.25 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.19 m³·mol⁻¹ChemAxon
Polarizability34.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+180.34832859911
AllCCS[M+H-H2O]+177.28632859911
AllCCS[M+Na]+183.99132859911
AllCCS[M+NH4]+183.17932859911
AllCCS[M-H]-179.46832859911
AllCCS[M+Na-2H]-179.132859911
AllCCS[M+HCOO]-178.83332859911
DeepCCS[M+H]+179.76330932474
DeepCCS[M-H]-177.18430932474
DeepCCS[M-2H]-212.20530932474
DeepCCS[M+Na]+188.49530932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
indole-3-acetyl-tyrosine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=C[NH]C3=CC=CC=C23)[Si](C)(C)C)C=C13204.3Semi standard non polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=C[NH]C3=CC=CC=C23)[Si](C)(C)C)C=C13115.9Standard non polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=C[NH]C3=CC=CC=C23)[Si](C)(C)C)C=C13793.1Standard polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(NC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C(=O)[O-])C=C13235.6Semi standard non polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(NC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C(=O)[O-])C=C13071.4Standard non polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(NC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C(=O)[O-])C=C13772.0Standard polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(CC1=CC=C(O)C=C1)C(=O)[O-]3190.0Semi standard non polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(CC1=CC=C(O)C=C1)C(=O)[O-]3178.1Standard non polar33892256
indole-3-acetyl-tyrosine,2TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(CC1=CC=C(O)C=C1)C(=O)[O-]3877.9Standard polar33892256
indole-3-acetyl-tyrosine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[Si](C)(C)C)C=C13186.9Semi standard non polar33892256
indole-3-acetyl-tyrosine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[Si](C)(C)C)C=C13083.5Standard non polar33892256
indole-3-acetyl-tyrosine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[Si](C)(C)C)C=C13556.5Standard polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=C[NH]C3=CC=CC=C23)[Si](C)(C)C(C)(C)C)C=C13767.1Semi standard non polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=C[NH]C3=CC=CC=C23)[Si](C)(C)C(C)(C)C)C=C13531.2Standard non polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=C[NH]C3=CC=CC=C23)[Si](C)(C)C(C)(C)C)C=C13863.2Standard polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(NC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C(=O)[O-])C=C13718.3Semi standard non polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(NC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C(=O)[O-])C=C13462.5Standard non polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(NC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C(=O)[O-])C=C13852.3Standard polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(CC1=CC=C(O)C=C1)C(=O)[O-]3677.7Semi standard non polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(CC1=CC=C(O)C=C1)C(=O)[O-]3552.4Standard non polar33892256
indole-3-acetyl-tyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(CC1=CC=C(O)C=C1)C(=O)[O-]3926.2Standard polar33892256
indole-3-acetyl-tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[Si](C)(C)C(C)(C)C)C=C13907.9Semi standard non polar33892256
indole-3-acetyl-tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[Si](C)(C)C(C)(C)C)C=C13635.5Standard non polar33892256
indole-3-acetyl-tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)[O-])N(C(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[Si](C)(C)C(C)(C)C)C=C13708.0Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - indole-3-acetyl-tyrosine 10V, Negative-QTOFsplash10-000i-0129000000-bdff2f3ab613cd6505ff2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - indole-3-acetyl-tyrosine 20V, Negative-QTOFsplash10-0apu-0943000000-1f996c0da3b5df584b532019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - indole-3-acetyl-tyrosine 40V, Negative-QTOFsplash10-01b9-5900000000-6f43ec79d6f2276a09e92019-02-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030933
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44123409
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available