ECMDB: Benzo[a]pyrene-7,8-diol (ECMDB20119) (M2MDB000967)

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

Proteins (892)

Record Information

Version

2.0

Creation Date

2012-05-31 14:28:29 -0600

Update Date

2015-06-03 17:19:21 -0600

Secondary Accession Numbers

ECMDB20119

Identification

Name:

Benzo[a]pyrene-7,8-diol

Description

Benzo[a]pyrene-7,8-diol is a member of the chemical class known as Pyrenes. These are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system. Benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide (BPDE), a metabolite of the widespread environmental pollutant benzo[a]pyrene, is a mutagenic in both bacterial and mammalian systems. (PMID 7890605)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(E)-3,7-dimethylocta-1,6-dien-3,8-diol
(E)-Benzo(a)pyrene-7,8-dihydrodiol
7,8-Dihydro 7,8-dihydroxybenzo(a)pyrene
7,8-Dihydro-7,8-dihydroxy-(E)-Benzo(a)pyrene
7,8-Dihydro-7,8-dihydroxy-Benzo(a)pyrene
7,8-Dihydro-7,8-dihydroxybenzopyrene
7,8-Dihydrobenzo(a)pyrene-7,8-diol
7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene
7,8-Diol-benzo(a)pyrene
Benzo(a)pyrene 7,8-dihydrodiol
Benzo(a)pyrene 7,8-dihydrodiol, (7R-trans)-isomer
Benzo(a)pyrene 7,8-dihydrodiol, (7S-trans)-isomer
Benzo(a)pyrene 7,8-dihydrodiol, (cis)-isomer
Benzo(a)pyrene 7,8-dihydrodiol, (trans)-(+-)-isomer
Benzo(a)pyrene 7,8-dihydrodiol, (trans)-isomer
Benzo(a)pyrene 7,8-diol
Benzo(a)pyrene-7,8-dihydrodiol
Benzo(a)pyrene-7,8-diol
Benzopyrene-7,8-dihydrodiol
Benzo[a]pyrene-7,8-dihydrodiol
BP-7,8 diol
BP-7,8-dihydrodiol
Cis-7,8-Dihydrobenzo[a]pyrendiol
Trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene
Trans-Benzopyrene 7,8-dihydrodiol

Chemical Formula:

C₂₀H₁₄O₂

Weight:

Average: 286.324
Monoisotopic: 286.099379692

InChI Key:

YDXRLMMGARHIIC-UHFFFAOYSA-N

InChI:

InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H

CAS number:

13345-25-0

IUPAC Name:

pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol

Traditional IUPAC Name:

benzo(a)pyrene 7,8-diol

SMILES:

OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Pyrenes

Sub Class

Not Available

Direct Parent

Pyrenes

Alternative Parents

Substituents

Pyrene
Phenanthrol
Phenanthrene
Naphthalene
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

pyrenes (CHEBI:34562 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	3.61	ALOGPS
logP	3.31	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.04 m³·mol⁻¹	ChemAxon
Polarizability	31.45 Å³	ChemAxon
Number of Rings	5	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:

Membrane

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	splash10-056r-0090000000-d0f9942584aaf480d999	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0103-8009100000-fe801e46e710eea32e4f	View in MoNA
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 (Non-derivatized) - 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 (TMS_1_1) - 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 (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-e746f506858cf64c915a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9i-1090000000-fcf1f10a896618157892	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-1290000000-d88f3784dd0a513870f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7c6172f7110a47ae0a1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-40d4296cbb4974e7d7c7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a70-1090000000-35194879c01560da4ee1	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:

Chary, P., Latham, G. J., Robberson, D. L., Kim, S. J., Han, S., Harris, C. M., Harris, T. M., Lloyd, R. S. (1995). "In vivo and in vitro replication consequences of stereoisomeric benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide adducts on adenine N6 at the second position of N-ras codon 61." J Biol Chem 270:4990-5000. Pubmed: 7890605
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	34562
HMDB ID	HMDB0060438
Pubchem Compound ID	25892
Kegg ID	C14852
ChemSpider ID	24123
Wikipedia ID	Not Available
BioCyc ID	E-37-DIMETHYLOCTA-16-DIEN-38-DIOL
EcoCyc ID	E-37-DIMETHYLOCTA-16-DIEN-38-DIOL

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

Benzo[a]pyrene-7,8-diol (ECMDB20119) (M2MDB000967)

Structure for #<Compound:0xa83613cc>

Enzymes

Reactions