8-Hydroxybenzo[a]pyrene

ID: ALA1908057

Cas Number: 13345-26-1

PubChem CID: 25893

Max Phase: Preclinical

Molecular Formula: C20H12O

Molecular Weight: 268.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 8-Hydroxybenzo[A]Pyrene | benzo[a]pyren-8-ol|13345-26-1|8-Hydroxybenzo[a]pyrene|Benzo(a)pyren-8-ol|BENZO(a)PYRENE, 8-HYDROXY-|8-Hydroxy-3,4-benzopyrene|Benzo[pqr]tetraphen-8-ol|CHEBI:34493|8-HYDROXYBENZO(A)PYRENE|8-Hydroxy-benzo(a)pyrene|BRN 2379758|8-Hydroxy benzo[a]pyrene|BIDD:ER0355|CHEMBL1908057|DTXSID00158116|AKOS015905883|CS-0098958|NS00124225|Q27116106|pentacyclo[10.6.2.0?,?.0?,??.0??,??]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-5-ol

Canonical SMILES:  Oc1ccc2c(c1)cc1ccc3cccc4ccc2c1c34

Standard InChI:  InChI=1S/C20H12O/c21-16-7-9-17-15(11-16)10-14-5-4-12-2-1-3-13-6-8-18(17)20(14)19(12)13/h1-11,21H

Standard InChI Key:  OWEZWMDNHHTXJU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 25  0  0  0  0  0  0  0  0999 V2000
  -12.9250    1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2105    1.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2105    2.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9250    2.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6395    2.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6395    1.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4961    2.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7816    2.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7816    1.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4961    1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0671    2.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3526    2.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3526    1.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0671    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4961    3.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7816    3.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0672    3.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3527    3.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6382    3.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6381    2.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3540    1.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
 10  2  1  0
  2  3  2  0
  3  7  1  0
  9 10  2  0
 14  9  1  0
  9  8  1  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
  8  7  2  0
 11  8  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 11 17  2  0
 12 11  1  0
 20 12  2  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1908057

   8-Hydroxybenzo[a]pyrene

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 268.31

Molecular Weight (Monoisotopic): 268.0888

AlogP: 5.44

#Rotatable Bonds: ┄

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.77

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 5

Heavy Atoms: 21

QED Weighted: 0.29

Np Likeness Score: 0.54

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

Source

Source(1):

• Scientific Literature