Aromatic amino acid (ECMDB23870) (M2MDB005520)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version2.0
Creation Date2015-06-08 15:28:30 -0600
Update Date2015-08-05 16:22:05 -0600
Secondary Accession Numbers
  • ECMDB23870
Identification
Name:Aromatic amino acid
DescriptionAmino acids that include an aromatic ring
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (+-)-5-Hydroxytryptophan
  • (S)-5-Hydroxytryptophan
  • 5-HTP
  • 5-Hydroxy-DL-tryptophan
  • 5-Hydroxy-tryptophan
  • 5-Hydroxyl-L-tryptophan
  • 5-Hydroxytryptophan
  • 5-Hydroxytryptophan DL-form
  • 5-Hydroxytryptophan L form
  • 5-Hydroxytryptophan L-form
  • Cincofarm
  • DL-5-HTP
  • DL-5-Hydroxytryptophan
  • Hydroxytryptophan
  • L-5-Hydroxytryptophan
  • Levothym
  • Levotinine
  • Oxitriptan
  • Oxyfan
  • Oxytryptophan
  • Pretonine
  • Quietim
  • Serotonyl
  • Telesol
  • Triptene
Chemical Formula:C11H12N2O3
Weight:Average: 220.2246
Monoisotopic: 220.08479226
InChI Key:LDCYZAJDBXYCGN-UHFFFAOYSA-N
InChI:InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)
CAS number:Not Available
IUPAC Name:2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Traditional IUPAC Name:DL-5-hydroxytryptophan
SMILES:NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.63 g/LALOGPS
logP-1.6ALOGPS
logP-1.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.18 m³·mol⁻¹ChemAxon
Polarizability22.03 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-Glutamate
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0390000000-3c19ae217ad78448c30fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0097-5920000000-eb294b94875b74adc6f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9067000000-2ab7fbf926f4f1b43002View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0090000000-823f10e31a9f15588233View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-0900000000-d763102ca4968c158d29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053r-0900000000-500716cec2e9f8383df7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00rx-2930000000-9e9f041cf524d559b331View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-44c37ec15a5546b1c353View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0910000000-5e6f9e21dd30ec8c20f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-b656dc85b8aff47fea96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-3900000000-94c7412dbb7cb04c9f32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0w29-0790000000-233a5164a2a4514e5bb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-0980000000-52f402588d34f0e4bf81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0910000000-f2841345d00a265d4104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900000000-df31c7e703c994b797feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2090000000-28b52756bfbd372bccf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9460000000-093dd610b11a147c2056View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9500000000-d567d2ab0b6a5e8a8a22View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28171
HMDB IDNot Available
Pubchem Compound ID144
Kegg IDC01021
ChemSpider IDNot Available
Wikipedia ID5-Hydroxytryptophan
BioCyc IDNot Available