ECMDB: 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene (ECMDB20078) (M2MDB000927)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (887)

Record Information

Version

2.0

Creation Date

2012-05-31 14:26:19 -0600

Update Date

2015-06-03 17:19:16 -0600

Secondary Accession Numbers

ECMDB20078

Identification

Name:

3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene

Description

3,4-dihydro-3-hydroxy-4-s-glutathionyl bromobenzene 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

Synonyms:

(2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-3-(4-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
(2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
L-g-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
L-gamma-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
L-γ-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine

Chemical Formula:

C₁₆H₂₂BrN₃O₇S

Weight:

Average: 480.331
Monoisotopic: 479.03618341

InChI Key:

WIPMNDWTVDZAHE-JYBOHDQNSA-N

InChI:

InChI=1S/C16H22BrN3O7S/c17-8-1-3-12(11(21)5-8)28-7-10(15(25)19-6-14(23)24)20-13(22)4-2-9(18)16(26)27/h1,3,5,9-12,21H,2,4,6-7,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t9-,10-,11?,12?/m0/s1

CAS number:

Not Available

IUPAC Name:

(2S)-2-amino-4-{[(1R)-2-[(4-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional IUPAC Name:

C16H22brN3O7S

SMILES:

[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC(Br)=CC1([H])O)C(O)=NCC(O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Hydroxy fatty acid
Halogenated fatty acid
Fatty amide
Fatty acyl
N-acyl-amine
Dicarboxylic acid or derivatives
Amino acid or derivatives
Amino acid
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Bromoalkene
Carboxylic acid
Haloalkene
Dialkylthioether
Sulfenyl compound
Vinyl halide
Vinyl bromide
Thioether
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Primary aliphatic amine
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

peptide (CHEBI:34324 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.4	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.86	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	106.82 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	1	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:

Bromobenzene-3,4-oxide + Glutathione <> 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene
Bromobenzene-3,4-oxide + Glutathione < 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene

SMPDB Pathways:

glutathione metabolism III

PW002018

KEGG Pathways:

Not Available

EcoCyc Pathways:

2,3-dihydroxybenzoate biosynthesis PWY-5901

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5922800000-c40ed874d9c5502a4d1a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-000y-5190108000-4782944b55c20ef6d12a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene,2TBDMS,#4" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02ha-2023900000-a99b2d602d251ac08e3b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9145100000-5e3af90d25319ad465d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9241000000-6ee8399683c139ed4a2c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0h00-0231900000-5c894a3884a1afaf36ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-0971100000-009d5316a5746058cd36	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-1920000000-d4ea4fbd0aa6eae7ab02	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	34324
HMDB ID	HMDB0060381
Pubchem Compound ID	11954066
Kegg ID	C14847
ChemSpider ID	10128361
Wikipedia ID	Not Available
BioCyc ID	DIHYDRO-DIOH-BENZOATE
EcoCyc ID	DIHYDRO-DIOH-BENZOATE

Enzymes

Protein Details

1. Glutathione S-transferase

General function:: Involved in protein binding
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:: gst
Uniprot ID:: P0A9D2
Molecular weight:: 22868

Reactions

RX + glutathione = HX + R-S-glutathione.

Protein Details

2. GSH-dependent disulfide bond oxidoreductase

General function:: Not Available
Specific function:: Not Available
Gene Name:: yfcG
Uniprot ID:: P77526
Molecular weight:: Not Available

3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene (ECMDB20078) (M2MDB000927)

Structure for #<Compound:0xac16a830>

Enzymes

Reactions