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56-69-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:72998 http://www.chembase.cn/molecule-72998.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.152664  H Acceptors
H Donor LogD (pH = 5.5) -1.3896201 
LogD (pH = 7.4) -1.3962954  Log P -1.3896985 
Molar Refractivity 58.1837 cm3 Polarizability 23.689636 Å3
Polar Surface Area 99.34 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off-White to Pale Beige Solid expand Show data source
Melting Point
254-259°C (dec.) expand Show data source
ca 298°C dec. expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
YN7100000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
TSCA Listed
expand Show data source
Purity
95+% expand Show data source
99% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals TRC TRC
MP Biomedicals - 05211575 external link
MP Biomedicals Rare Chemical collection
Selleck Chemicals - S2374 external link
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 external link
A metabolite of Tryptophan. 5-Hydroxytryptophan (5-HTP) is a direct 5-hydroxytryptamine (5-HT) precursor used to assess central serotonergic function.

REFERENCES

REFERENCES

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  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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