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Record Information
Version	2.0
Creation Date	2015-06-08 15:28:30 -0600
Update Date	2015-08-05 16:22:05 -0600
Secondary Accession Numbers	ECMDB23870
Identification
Name:	Aromatic amino acid
Description	Amino acids that include an aromatic ring
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa6c8af68> Close
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.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Indoles and derivatives
Sub Class	Tryptamines and derivatives
Direct Parent	Serotonins
Alternative Parents	Indolyl carboxylic acids and derivatives 3-alkylindoles Alpha amino acids Hydroxyindoles 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Substituted pyrroles Heteroaromatic compounds Amino acids Carboxylic acids Azacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Carbonyl compounds Monoalkylamines Organic oxides Hydrocarbon derivatives
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	hydroxytryptophan (CHEBI:28171 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.63 g/L ALOGPS logP -1.6 ALOGPS logP -1.4 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 2.15 ChemAxon pKa (Strongest Basic) 9.18 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 99.34 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 58.18 m³·mol⁻¹ ChemAxon Polarizability 22.03 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-Glutamate
SMPDB Pathways:	Lysine biosynthesis PW000771 Phenylalanine metabolism PW000921
KEGG Pathways:	Cysteine and methionine metabolism ec00270 Isoquinoline alkaloid biosynthesis ec00950 Lysine biosynthesis ec00300 Metabolic pathways eco01100 Novobiocin biosynthesis ec00401 Phenylalanine metabolism ec00360 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Tyrosine metabolism ec00350
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0006-0390000000-3c19ae217ad78448c30f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0097-5920000000-eb294b94875b74adc6f8 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00dl-9067000000-2ab7fbf926f4f1b43002 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-00di-0090000000-823f10e31a9f15588233 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-053r-0900000000-d763102ca4968c158d29 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-053r-0900000000-500716cec2e9f8383df7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - , negative splash10-00rx-2930000000-9e9f041cf524d559b331 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-0udi-0090000000-44c37ec15a5546b1c353 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-03di-0910000000-5e6f9e21dd30ec8c20f3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-001i-0900000000-b656dc85b8aff47fea96 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-001i-3900000000-94c7412dbb7cb04c9f32 View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-0w29-0790000000-233a5164a2a4514e5bb9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0fi0-0980000000-52f402588d34f0e4bf81 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-0910000000-f2841345d00a265d4104 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014j-0900000000-df31c7e703c994b797fe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-2090000000-28b52756bfbd372bccf4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-9460000000-093dd610b11a147c2056 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00e9-9500000000-d567d2ab0b6a5e8a8a22 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 28171 HMDB ID Not Available Pubchem Compound ID 144 Kegg ID C01021 ChemSpider ID Not Available Wikipedia ID 5-Hydroxytryptophan BioCyc ID Not Available