2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

• ChemBase ID: 72998
• Molecular Formular: C11H12N2O3
• Molecular Mass: 220.22458
• Monoisotopic Mass: 220.08479225
• SMILES: c1(ccc2c(c1)c(c[nH]2)CC(C(=O)O)N)O
• Canonical SMILES: OC(=O)C(Cc1c[nH]c2c1cc(O)cc2)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)
• InChIKey: LDCYZAJDBXYCGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: (+-)-5-hydroxytryptophan; tryptophan, 5-hydroxy-, DL-
• Synonyms: 5-HTP; 5-hydroxytryptophan; DL-5-HYDROXYTRYPTOPHANE; (+/-)-5-Hydroxytryptophan; 5-Hydroxy-DL-tryptophan; DL-Hydroxytryptophan; NSC 92523; 5-Hydroxy Tryptophan; DL-5-Hydroxytryptophan; DL-2-Amino-3-[3-(5-hydroxyindole)]propionic acid; 2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid; DL-5-羟基色氨酸

Database IDs

• CAS Number: 114-03-4; 56-69-9
• EC Number: 200-284-8
• MDL Number: MFCD00005651
• Beilstein Number: 88199
• Merck Index: 144847
• PubChem SID: 162037918
• PubChem CID: 144

CALCULATED PROPERTIES

• Acid pKa: 2.152664
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.3896201
• LogD (pH = 7.4): -1.3962954
• Log P: -1.3896985
• Molar Refractivity: 58.1837 cm^3
• Polarizability: 23.689636 Å^3
• Polar Surface Area: 99.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 254-259°C (dec.); ca 298°C dec.

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: YN7100000
• TSCA Listed: 是

Product Information

• Purity: 95+%; 99%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 05211575

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2374

Biological Activity:
5-Hydroxytryptophan(5-HTP) is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase with the help of Vitamin B6.This reaction occurs both in nervous tissue and in the liver. 5-HTP crosses the blood-brain barrier，while 5-HT does not. Excess 5-HTP, especially when administered with Vitamin B6, is thought to be metabolized and excreted. The psychoactive action of 5-HTP is derived from its effect on the production of serotonin in central nervous system tissue. More specifically, 5-HTP increases the production of serotonin. Thus, it has been used to treat diseases, e.g. depression, for which the lack of serotonin is thought to be a contributing factor. [1]

Toronto Research Chemicals - H975700

A metabolite of Tryptophan. 5-Hydroxytryptophan (5-HTP) is a direct 5-hydroxytryptamine (5-HT) precursor used to assess central serotonergic function.

REFERENCES

• http://en.wikipedia.org/wiki/5-HTP
• Gartside, S., et al.: Eur. J. Pharmacol., 179, 103 (1990)
• Gijsman, H., et al.: J. Clin. Psychopharmacol., 22, 183 (1990)
• Schruers, K., et al.: Psychiatry Res., 113, 237 (1990)