NP-MRD: Showing NP-Card for benzo(e)pyrene (NP0173153)

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Record Information

Version

2.0

Created at

2022-09-03 10:14:39 UTC

Updated at

2022-09-03 10:14:39 UTC

NP-MRD ID

NP0173153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

benzo(e)pyrene

Description

Benzo[e]pyrene, also known as 1,2-benzpyrene or b(e)p, belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Benzo[e]pyrene is possibly neutral. Benzopyrene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). Benzo[e]pyrene is a potentially toxic compound. They are usually found as a mixture containing two or more of these compounds. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. These enzymes metabolize PAH's into their toxic intermediates. benzo(e)pyrene is found in Nicotiana tabacum. benzo(e)pyrene was first documented in 2014 (PMID: 24812998). The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis (PMID: 25903191).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272019092D          

 20 24  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  2  0  0  0  0
  8 16  2  0  0  0  0
  9 17  2  0  0  0  0
 10 18  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 19  2  0  0  0  0
 14 20  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H12/c1-2-8-16-15(7-1)17-9-3-5-13-11-12-14-6-4-10-18(16)20(14)19(13)17/h1-12H

> <INCHI_KEY>
TXVHTIQJNYSSKO-UHFFFAOYSA-N

> <FORMULA>
C20H12

> <MOLECULAR_WEIGHT>
252.3093

> <EXACT_MASS>
252.093900384

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.882541022374802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

> <ALOGPS_LOGP>
6.33

> <JCHEM_LOGP>
5.273404237333333

> <ALOGPS_LOGS>
-8.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
83.1728

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.080   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.160   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.160   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.850   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    5    9                                                       
CONECT    4    6   10                                                       
CONECT    5    3   13                                                       
CONECT    6    4   14                                                       
CONECT    7    1   15                                                       
CONECT    8    2   16                                                       
CONECT    9    3   17                                                       
CONECT   10    4   18                                                       
CONECT   11   12   13                                                       
CONECT   12   11   14                                                       
CONECT   13    5   11   19                                                  
CONECT   14    6   12   20                                                  
CONECT   15    7   16   17                                                  
CONECT   16    8   15   18                                                  
CONECT   17    9   15   19                                                  
CONECT   18   10   16   20                                                  
CONECT   19   13   17   20                                                  
CONECT   20   14   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Value	Source
1,2-Benzopyrene	ChEBI
1,2-Benzpyrene	ChEBI
4,5-Benzopyrene	ChEBI
4,5-Benzpyrene	ChEBI
9,10-Benzpyrene	ChEBI
b(e)p	ChEBI
Benzo(e)pyrene	ChEBI
Benzo(L)pyrene	ChEBI
1,2-benzo(e)Pyrene	MeSH

Chemical Formula

C₂₀H₁₂

Average Mass

252.3093 Da

Monoisotopic Mass

252.09390 Da

IUPAC Name

pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

Traditional Name

pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

CAS Registry Number

Not Available

SMILES

C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3

InChI Identifier

InChI=1S/C20H12/c1-2-8-16-15(7-1)17-9-3-5-13-11-12-14-6-4-10-18(16)20(14)19(13)17/h1-12H

InChI Key

TXVHTIQJNYSSKO-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nicotiana tabacum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzo-e-pyrene
Triphenylene
Phenanthrene
Anthracene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ortho- and peri-fused polycyclic arene (CHEBI:34567 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.33	ALOGPS
logP	5.27	ChemAxon
logS	-8.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.17 m³·mol⁻¹	ChemAxon
Polarizability	28.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14435

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzo(e)pyrene

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

34567

Good Scents ID

Not Available

References

General References

Arulazhagan P, Sivaraman C, Kumar SA, Aslam M, Banu JR: Co-metabolic degradation of benzo(e)pyrene by halophilic bacterial consortium at different saline conditions. J Environ Biol. 2014 May;35(3):445-52. [PubMed:24812998 ]
Shang J, Chen J, Shen Z, Xiao X, Yang H, Wang Y, Ruan A: Photochemical degradation of PAHs in estuarine surface water: effects of DOM, salinity, and suspended particulate matter. Environ Sci Pollut Res Int. 2015 Aug;22(16):12374-83. doi: 10.1007/s11356-015-4543-2. Epub 2015 Apr 23. [PubMed:25903191 ]
LOTUS database [Link]

Showing NP-Card for benzo(e)pyrene (NP0173153)

MOL for NP0173153 (benzo(e)pyrene)

3D MOL for NP0173153 (benzo(e)pyrene)

3D SDF for NP0173153 (benzo(e)pyrene)

3D-SDF for NP0173153 (benzo(e)pyrene)

PDB for NP0173153 (benzo(e)pyrene)

3D PDB for NP0173153 (benzo(e)pyrene)

SMILES for NP0173153 (benzo(e)pyrene)

INCHI for NP0173153 (benzo(e)pyrene)

Structure for NP0173153 (benzo(e)pyrene)

3D Structure for NP0173153 (benzo(e)pyrene)