P. aeruginosa Metabolome Database: (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene (PAMDB000853)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000853

Identification

Name:

(1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene

Description:

(1r)-hydroxy-(2r)-glutathionyl-1,2-dihydronaphthalene belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(1R, 2S)-1,2-dihydronaphthalene-1,2-diol
(1R,2S)-1,2-dihydro-1,2-dihyroxynaphthalene
(1R,2S)-1,2-dihydronaphthalene-1,2-diol
(1R,2S)-naphthalene-1,2-dihydrodiol
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-1-Hydroxy-1,2-dihydronaphthalen-2-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-1-hydroxy-1,2-dihydronaphthalen-2-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-1-Hydroxy-1,2-dihydronaphthalen-2-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-1-Hydroxy-1,2-dihydronaphthalen-2-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
3,4-dihydronaphthalene-3,4-diol
cis-1,2-dihydronaphthalene-1,2-diol
cis-1,2-Dihydronaphthalene-1,2-diol
Cis-1,2-dihydroxy-1,2-dihydronaphthalene
L-g-Glutamyl-S-(1R,2R)-1-hydroxy-1,2-dihydro-2-naphthalenyl-L-cysteinylglycine
L-gamma-Glutamyl-S-(1R,2R)-1-hydroxy-1,2-dihydro-2-naphthalenyl-L-cysteinylglycine
L-γ-Glutamyl-S-(1R,2R)-1-hydroxy-1,2-dihydro-2-naphthalenyl-L-cysteinylglycine

Chemical Formula:

C₂₀H₂₅N₃O₇S

Average Molecular Weight:

451.493

Monoisotopic Molecular Weight:

451.141320859

InChI Key:

HBBDHJOSZGOTBV-OIPACUDHSA-N

InChI:

InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(24)23-14(19(28)22-9-17(25)26)10-31-15-7-5-11-3-1-2-4-12(11)18(15)27/h1-5,7,13-15,18,27H,6,8-10,21H2,(H,22,28)(H,23,24)(H,25,26)(H,29,30)/t13-,14-,15+,18+/m0/s1

CAS number:

Not Available

IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

SMILES:

[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C=CC2=CC=CC=C2[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-aliphatic-alpha amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
D-alpha-amino acid
Naphthalene
Alpha-amino acid or derivatives
Alpha-amino acid
Amino fatty acid
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Secondary alcohol
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Thioether
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0576 mg/mL	ALOGPS
logP	-1.6	ALOGPS
logP	-1.7	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.03 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	114.1 m³·mol^-1	ChemAxon
Polarizability	44.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene

Pathways:

Glutathione metabolism pae00480

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00e9-2126900000-1b7006b87834305a79f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9226100000-d8fd93086d00e09aaedc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9321000000-9198956786ba979c68f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zir-0513900000-b60008cc9c9ba81f90a2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-0910000000-16406d930e33b85c278c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-1900000000-66a973bc3e3243bef84a	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB60300
Pubchem Compound ID	11954044
Kegg ID	C14791
ChemSpider ID	10128339
Wikipedia ID	Not Available
BioCyc ID	CIS-12-DIHYDRONAPHTHALENE-12-DIOL
EcoCyc ID	CIS-12-DIHYDRONAPHTHALENE-12-DIOL

Enzymes

Protein Details

• GSH-dependent disulfide bond oxidoreductase

General function:: Not Available
Specific function:: Not Available
Gene Name:: yfcG
Locus Tag:: PA1033
Molecular weight:: 24.5 kDa

(1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene (PAMDB000853)

Structure for (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene (PAMDB000853)

Enzymes