(2S)-2-amino-3-[5-hydroxy(2,4,6,7-2H4)-1H-indol-3-yl]propanoic acid

• ChemBase ID: 171419
• Molecular Formular: C11H12N2O3
• Molecular Mass: 220.22458
• Monoisotopic Mass: 220.08479225
• SMILES: c1(ccc2c(c1)c(c[nH]2)C[C@H](N)C(=O)O)O
• Canonical SMILES: OC(=O)[C@H](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)/t9-/m0/s1
• InChIKey: LDCYZAJDBXYCGN-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[5-hydroxy(2,4,6,7-^2H₄)-1H-indol-3-yl]propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-[5-hydroxy(2,4,6,7-^2H₄)-1H-indol-3-yl]propanoic acid
• Synonyms: (S)-5-Hydroxytryptophan-d4; 5-Hydroxyl-L-tryptophan-d4; 5-Hydroxytryptophan-d4; Cincofarm-d4; L-5-HTP-d4; L-5-Hydroxytryptophan-d4; Levothym-d4; Levotinine-d4; Oxitriptan-d4; Oxyfan-d4; Pretonine-d4; Quietim-d4; Serotonyl-d4; Telesol-d4; Tript-Oh-d4; Triptene-d4; 5-Hydroxy L-Tryptophan-d4 (Major)

Database IDs

• CAS Number: 1246818-91-6
• PubChem SID: 164227329
• PubChem CID: 71749398

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: 23.710655 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: Dark Grey Solid
• Melting Point: >215°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H975712

A labelled metabolite of Tryptophan.

REFERENCES

• 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)