ChemFOnt: Showing chemical card for D-Tryptophan (CFc000008509)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:19 UTC

Chemfont ID

CFc000008509

Molecule Identification

Common Name

D-Tryptophan

Definition

Tryptophan (Trp or W) (sold for medical use as Tryptan) is one of the 20 standard amino acids. Its distinguishing structural characteristic is its indole functional group. The D-stereoisomer is occasionally found in naturally produced peptides (e.g. contryphan, the marine venom peptide).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Amino-3-(1H-indol-3-yl)propanoic acid	ChEBI
(R)-Tryptophan	ChEBI
DTR	ChEBI
(2R)-2-Amino-3-(1H-indol-3-yl)propanoate	Generator
(+)-Tryptophan	HMDB
(R)-(+)-2-amino-3-(3-Indolyl)propionic acid	HMDB
(R)-2-amino-3-(3-Indolyl)propionic acid	HMDB
D-(+)-Tryptophan	HMDB
D-alpha-amino-3-Indolepropionic acid	HMDB
D-Tryptophane	HMDB
D-Trytophane	HMDB
delta-(+)-Tryptophan	HMDB
delta-alpha-amino-3-Indolepropionic acid	HMDB
delta-Tryptophane	HMDB
delta-Trytophane	HMDB
DL-Tryptophan	HMDB
H-D-TRP-OH	HMDB
H-delta-TRP-OH	HMDB
Tryptophan	HMDB

Chemical Formula

C₁₁H₁₂N₂O₂

Average Molecular Weight

204.2252

Monoisotopic Molecular Weight

204.089877638

IUPAC Name

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

Traditional Name

D-tryptophan

CAS Registry Number

153-94-6

SMILES

N[C@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

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-/m1/s1

InChI Key

QIVBCDIJIAJPQS-SECBINFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:16296 )
tryptophan (CHEBI:16296 )
Other amino acids (C00525 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 26847922)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (PMID: 28157703)

Source

Exogenous

Exogenous (HMDB: HMDB0013609)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0013609)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0013609)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.2 m³·mol⁻¹	ChemAxon
Polarizability	21.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon