D-Tryptophan (YMDB00998)

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Identification

YMDB ID

YMDB00998

Name

D-Tryptophan

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Tryptophan, also known as DTR, 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. D-Tryptophan exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on D-Tryptophan.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-tryptophan
(2R)-2-amino-3-(1H-indol-3-yl)propanoate
(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
(R)-(+)-2-Amino-3-(3-indolyl)propionic acid
(R)-2-Amino-3-(3-indolyl)propionic acid
(r)-tryptophan
D-(+)-tryptophan
D-alpha-Amino-3-indolepropionic acid
D-Tryptophan
D-tryptophane
D-trytophane
delta-(+)-tryptophan
delta-alpha-Amino-3-indolepropionic acid
delta-tryptophane
delta-trytophane
DL-tryptophan
DTR
H-d-TRP-oh
H-delta-TRP-oh
Tryptophan
Tryptophan, D-

CAS number

153-94-6

Weight

Average: 204.2252
Monoisotopic: 204.089877638

InChI Key

QIVBCDIJIAJPQS-SECBINFHSA-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-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

D-tryptophan

Chemical Formula

C₁₁H₁₂N₂O₂

SMILES

N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O

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 )

Physical Properties

State

Solid

Charge

Melting point

230 °C

Experimental Properties

Property	Value	Reference
Water Solubility	13.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-1.06 [HANSCH,C ET AL. (1995)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-4900000000-fa932bc4cffed0ca66b7	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gl-7490000000-c8150f8039963f4eb7f7	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0gi0-4940000000-00a5a8140b79080185e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0gi0-3940000000-321dc703abd716322faa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0uxr-1960000000-3944aa089c0be5dbd57a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0900000000-94061fd1f6b08445cdf3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-0930000000-da94834297fcc5b3d3c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 25V, Negative	splash10-0zfr-0890000000-0d359faeb8858c021feb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-e78172f4f27df232466e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0790000000-b95264f9ab4278178457	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0900000000-e13b1ada6628c7f81fad	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-014i-0900000000-93406e2cdb79770abc7d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-c73c9b49139319c80b18	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 65V, Negative	splash10-0udi-0690000000-4bf908b56440e171f545	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-0udi-0190000000-dfe53dc7eb1d8480b67d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 95V, Negative	splash10-014i-1910000000-d9efdaa0c5d83afa0a30	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090000000-3f6a5d549dc480992733	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-d8162407bfd6d77329dd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0udi-0390000000-99187dba9accfe70a9d7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 80V, Negative	splash10-0gb9-1940000000-6731b16a7a3f99824a8f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-71ce6030cb0ece21c187	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 70V, Negative	splash10-0uxr-1980000000-f81e0966edca14970bcd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0890000000-8d614cd4a32f54f5f42b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 55V, Negative	splash10-0udi-0290000000-f509dc2b1981bd74e940	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-0900000000-ad4c64ffc9170a5bae1e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0udi-0190000000-4aff7b2f76290f449a84	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-014i-0920000000-a9d3f1ce81f54000d79c	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2004). "D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids." Arch Microbiol 182:396-403.15375647

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16296
HMDB ID	HMDB13609
Pubchem Compound ID	9060
Kegg ID	C00525
ChemSpider ID	8707
FOODB ID	FDB029595
Wikipedia	Tryptophan
BioCyc ID	D-TRYPTOPHAN

Enzymes

Protein Details

1. N-acetyltransferase HPA3

General function:: Involved in N-acetyltransferase activity
Specific function:: N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:: HPA3
Uniprot ID:: P39979
Molecular weight:: 20698.5

Reactions

acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid

Structure for #<Compound:0xafa595ec>

Enzymes

Reactions