L-Tryptophanamide
Basic information
- CAS
20696-57-5- Standard SMILES
NC(=O)[C@@H](N)Cc1c[nH]c2ccccc12- InChIKey
JLSKPBDKNIXMBS-VIFPVBQESA-N- Molecular formula
- C11H13N3O
- Average molar mass
- 203.24 g/mol
- Monoisotopic mass
- 203.10586205
Overview
L-tryptophanamide is an amino acid amide that is the carboxamide of L-tryptophan. It has a role as a human metabolite. It is an amino acid amide and a tryptophan derivative. It is a conjugate base of a L-tryptophanamide(1+).
Names & identifiers
- Preferred name
- L-Tryptophanamide
- IUPAC
- (2S)-2-amino-3-(1H-indol-3-yl)propanamide
- English name
- (S)-alpha-amino-1H-indole-3-propionamide
- Molecular formula
- C11H13N3O
- Molecular weight
- 203.24
Names & synonyms
L-TryptophanamideTryptophanamide20696-57-5S-TryptophanamideTryptophanamide, L-(2S)-2-amino-3-(1H-indol-3-yl)propanamideL-tryptophan amide0K2B9SB26HCHEBI:16533DTXSID8013165071H-Indole-3-propanamide, alpha-amino-, (S)-(2S)-2-azanyl-3-(1H-indol-3-yl)propanamide
Show more names
C00977H-Trp-NH2(S)--amino-1H-indole-3-propionamide(S)-α-Amino-1H-indole-3-propanamide(aS)-a-amino-1H-Indole-3-propanamide1H-Indole-3-propanamide, α-amino-, (αS)-
RefChem:900690DTXCID001746352243-977-0alpha-Amino-1H-indole-3-propanamide(S)-2-Amino-3-(1H-indol-3-yl)propanamide(S)-alpha-Amino-1H-indole-3-propionamideCHEMBL227123MFCD11111547
Database identifiers
- CAS
20696-57-5- PubChem CID
- 439356
- DTXSID
DTXSID801316507- ChEMBL
CHEMBL227123- ChEBI
CHEBI:16533
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 84.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 244
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section
150.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
143.5 Ų [M-H]-
Physicochemical properties
- Melting point
- 254 · 254-255 °C (decomp)(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
- Boiling point
- 498.7 · 498.7±40.0 °C(Predicted)
- Density
- 1.302 · 1.302±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 15.99 · 15.99±0.50(Predicted)
- FDA UNII
- 0 K2B9SB26H · 0K2B9SB26H
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 264 · P264-P270-P301+P310+P330-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301
- Precautionary statements
- P264-P270-P301+P310+P330-P405-P501
Chemistry & industry
Applications
UsesL-Tryptophanamide is a compound discovered in wet age-related macular degeneration research, which has activities related to affecting retinal cell proliferation, apoptosis, necrosis and angiogenesis. In in vitro experiments, L-Tryptophanamide affects the proliferation, apoptosis and necrosis of human retinal pigment epithelial cells, and promotes tube formation and migration of human retinal endothelial cells.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: An amino acid amide that is the carboxamide of L-tryptophan.
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