12-Hydroxybenzo[a]pyrene

ID: ALA1908002

Cas Number: 56892-33-2

PubChem CID: 42030

Max Phase: Preclinical

Molecular Formula: C20H12O

Molecular Weight: 268.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 12-Hydroxybenzo[A]Pyrene | 12-Hydroxybenzo[a]pyrene|12-Hydroxybenzo(a)pyrene|benzo[a]pyren-12-ol|56892-33-2|BENZO(a)PYREN-12-OL|CHEBI:34149|Benzo(a)pyrene, 12-hydroxy-|BRN 2464086|12-Hydroxy benzo[a]pyrene|QEW2PN472R|Hydroxybenzo[a]pyrene, 12-|BIDD:ER0544|CHEMBL1908002|DTXSID60205418|NS00073982|Q27115846

Canonical SMILES:  Oc1cc2c3ccccc3cc3ccc4cccc1c4c32

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

Standard InChI Key:  XWSLTTWKRKWHAT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 25  0  0  0  0  0  0  0  0999 V2000
   -7.2875   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5730    0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5730    1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2875    1.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0020    1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0020    0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7164    1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4309    1.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4309    0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7164   -0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1454    1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8599    1.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8599    0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1454   -0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7164    2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0020    2.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2875    2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5730    2.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8585    2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8585    1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0020    3.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  6  1  1  0
  6  5  1  0
 10  6  2  0
  7  8  1  0
  9 10  1  0
  8 11  1  0
  9  8  2  0
 14  9  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  5  7  2  0
  7 15  1  0
  4  5  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  4 17  2  0
  3  4  1  0
 20  3  2  0
 18 19  2  0
 19 20  1  0
 16 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1908002

   12-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: 9.30

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.96

Aromatic Rings: 5

Heavy Atoms: 21

QED Weighted: 0.29

Np Likeness Score: 0.43

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