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Record Information

Version

2.0

Creation Date

2012-05-31 14:28:00 -0600

Update Date

2015-06-03 17:19:20 -0600

Secondary Accession Numbers

ECMDB20110

Identification

Name:

7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene

Description

7,8-dihydro-7-hydroxy-8-s-glutathionyl-benzo[a]pyrene 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 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(7-Hydroxy-7,8-dihydrobenzoapyren-8-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(7-hydroxy-7,8-dihydrobenzoapyren-8-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(7-Hydroxy-7,8-dihydrobenzoapyren-8-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(7-Hydroxy-7,8-dihydrobenzoapyren-8-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzoapyrene

Chemical Formula:

C₃₀H₂₉N₃O₇S

Weight:

Average: 575.632
Monoisotopic: 575.172620987

InChI Key:

GODDWIDSELPRPA-QMIJOYDGSA-N

InChI:

InChI=1S/C30H29N3O7S/c31-21(30(39)40)9-11-24(34)33-22(29(38)32-13-25(35)36)14-41-23-10-8-18-19-7-6-16-3-1-2-15-4-5-17(27(19)26(15)16)12-20(18)28(23)37/h1-8,10,12,21-23,28,37H,9,11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,23?,28?/m0/s1

CAS number:

Not Available

IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({6-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaen-5-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-({6-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaen-5-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

SMILES:

[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1([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
Pyrene
Phenanthrol
Glutamine or derivatives
Phenanthrene
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Naphthalene
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid
L-alpha-amino acid
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Amino acid
Amino acid or derivatives
Dialkylthioether
Carboxylic acid
Sulfenyl compound
Thioether
Primary amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Primary aliphatic amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

glutathione derivative (CHEBI:34479 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	0.06	ALOGPS
logP	0.65	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	2	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	154.77 m³·mol⁻¹	ChemAxon
Polarizability	59.38 Å³	ChemAxon
Number of Rings	5	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:

Benzo[a]pyrene-7,8-diol + Glutathione <> 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Water

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3090080000-8519d7cf79a00a63518e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-5091037000-e136a14541d7a630c317	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ac1-2011390000-c17170d5dab2882630a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9013520000-f614b00b9f7be9b2dff8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9032100000-788866d98b35d7db56e0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kn9-0023090000-8d4f41ebf042a44dbbb3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f89-0196020000-280209a3923d7422853d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-2942000000-61ab057e31d6584c15b3	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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	34479
HMDB ID	HMDB0060423
Pubchem Compound ID	11954069
Kegg ID	C14856
ChemSpider ID	10128364
Wikipedia ID	Not Available
BioCyc ID	Not Available

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

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene (M2MDB000958)

Structure for #<Compound:0xaa27bba4>

Enzymes

Reactions