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153-94-6 molecular structure
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(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

ChemBase ID: 36
Molecular Formular: C11H12N2O2
Molecular Mass: 204.22518
Monoisotopic Mass: 204.08987763
SMILES and InChIs

SMILES:
OC(=O)[C@@H](N)Cc1c2c([nH]c1)cccc2
Canonical SMILES:
OC(=O)[C@H](Cc1c[nH]c2c1cccc2)N
InChI:
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
InChIKey:
QIVBCDIJIAJPQS-VIFPVBQESA-N

Cite this record

CBID:36 http://www.chembase.cn/molecule-36.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
IUPAC Traditional name
L-tryptophan
L-tryptophan(.)
Brand Name
Alti-Tryptophan
Lyphan
Synonyms
(-)-Tryptophan
L-(-)-Tryptophan
L-Tryptophane
Tryptophan
Tryptophane
alpha-Amino-beta-(3-indolyl)-propionic acid
l-a-Aminoindole-3-propionic acid
l-b-3-Indolylalanine
(S)-a-Amino-1H-indole-3-propanoic acid
(S)-a-Amino-b-indolepropionic acid
(S)-a-Aminoindole-3-propionic acid
(S)-Tryptophan
2-Amino-3-indolylpropanoic acid
3-Indol-3-ylalanine
L-Tryptophan
2-Amino-3-(1H-indol-3-yl)propanoic acid
D-2-Amino-3-indolepropionic acid
D-TRYPTOPHAN
L-Trytophane
Indole-3-Alanine
alpha-Amino-3-Indoleproprionic Acid
(S)-2-amino-3-(1H-indol-3-yl)propanoic acid
2-Amino-3-(1H-indol-3-yl)propanoic acid
Tryptophan
L-TRYPTOPHAN, U.S.P.
L-Tryptophan
(S)-2-Amino-3-(3-indolyl)propionic acid
L-α-Amino-3-indolepropionic acid
(+/-)-Tryptophan
(-)-1H-Indole-3-alanine
NSC 13119
l-α-Aminoindole-3-propionic Acid
H-Trp-OH
L-2-Amino-3-indolepropionic acid
(S)-2-氨基-3-(3-吲哚基)丙酸
L-α-氨基-3-吲哚丙酸
L-色氨酸
L-色胺酸
CAS Number
153-94-6
73-22-3
EC Number
200-795-6
205-819-9
MDL Number
MFCD00064340
Beilstein Number
86197
Merck Index
149797
PubChem SID
24889916
24278135
24900575
160963499
24900200
46508329
PubChem CID
6305
CHEBI ID
27897
ATC CODE
N06AX02
CHEMBL
54976
Chemspider ID
6066
DrugBank ID
DB00150
IUPHAR ligand ID
717
KEGG ID
D00020
Unique Ingredient Identifier
8DUH1N11BX
Wikipedia Title
Tryptophan

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.5439286  H Acceptors
H Donor LogD (pH = 5.5) -1.0856168 
LogD (pH = 7.4) -1.0892947  Log P -1.085457 
Molar Refractivity 56.2028 cm3 Polarizability 23.092001 Å3
Polar Surface Area 79.11 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.1  LOG S -2.18 
Solubility (Water) 1.36e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.5 M HCl: soluble0.1 g/mL at 20 °C, clear, colorless to faintly yellow expand Show data source
1 M HCl: soluble10 mg/mL expand Show data source
Soluble expand Show data source
Soluble in hot alcohol, alkali hydroxides; insoluble in chloroform. expand Show data source
Soluble: 0.23 g/L at 0 °C,
11.4 g/L at 25 °C,
17.1 g/L at 50 °C,
27.95 g/L at 75 °C in water
expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
>246°C (dec.) expand Show data source
280°C 285°C expand Show data source
280-285 °C (dec.)(lit.) expand Show data source
289°C expand Show data source
Optical Rotation
[α]20/D -31.5±1°, c = 1% in H2O expand Show data source
[α]20/D -31.5°, c = 1 in H2O expand Show data source
-31 (c=1 in water) expand Show data source
Hydrophobicity(logP)
-1.3 expand Show data source
pKa
2.38 (carboxyl), 9.39 (amino) expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
Room Temperature (15-30°C), Protect from light expand Show data source
RTECS
YN6129000 expand Show data source
YN6130000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Gene Information
human ... TDO2(6999), TPH1(7166), TPH2(121278) expand Show data source
Purity
≥99% expand Show data source
≥98% (TLC) expand Show data source
≥98.5% expand Show data source
≥99.5% (NT) expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
99.0-101.0% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
JP expand Show data source
reagent grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Optical Purity
ee: 99% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP, JP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% expand Show data source
Impurities
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤50 mg/kg expand Show data source
sulfate (SO42-): ≤50 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.1% loss on drying, 20 °C (HV) expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
Product Line
BioUltra expand Show data source
abs.
absorption0.5M/326 nm, 0.5 M HCl cut-off expand Show data source
Empirical Formula (Hill Notation)
C11H12N2O2 expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia TRC TRC
DrugBank - DB00150 external link
Item Information
Drug Groups approved; nutraceutical
Description An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem]
Indication Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
Pharmacology Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).
Toxicity Oral rat LD50: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
MP Biomedicals - 02194758 external link
Cell Culture Reagent
Purity: 99+%
Crystalline
MP Biomedicals - 02199561 external link
White powder
MP Biomedicals - 02103144 external link
Crystalline
Purity: 99%
MP Biomedicals - 02103151 external link
Purity: 99+%
Crystalline
Sigma Aldrich - 93659 external link
Other Notes
Amino acid precursor of serotonin and melatonin
In tryptophan-substituted Sephadex® and Sepharose® for the improved chromatographic separation of cellulases1; As spacer in isotachophoresis of serum proteins2; Growth requirement of various microorganisms3.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 93659.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Legal Information
Sephadex is a registered trademark of GE Healthcare
Sepharose is a registered trademark of GE Healthcare
Sigma Aldrich - T4196 external link
Other Notes
Amino acid precursor of serotonin and melatonin
Packaging
Manufactured and packaged under cGMP
Sigma Aldrich - T8941 external link
Other Notes
血清素和褪黑激素的氨基酸前体
包装
10 mg in autosmp vl
Sigma Aldrich - T0254 external link
Other Notes
血清素和褪黑激素的氨基酸前体
包装
1 kg in poly bottle
1, 5, 25, 100, 500 g in poly bottle
Sigma Aldrich - T90204 external link
Other Notes
Amino acid precursor of serotonin and melatonin
Application
Employed in the synthesis of bridged indole alkaloids.1
Sigma Aldrich - 51145 external link
Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Other Notes
Amino acid precursor of serotonin and melatonin
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - T947210 external link
Essential amino acid.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Goze, C., et al.: Eur. J. Pharmacol., 643, 153 (2010)
  • • Bhandare, P., et al.: J. Chem. Pharm. Res., 2, 372 (2010)
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PATENTS

PATENTS

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