4-Hydroxybenzo[a]pyrene

ID: ALA1908016

Cas Number: 37574-48-4

PubChem CID: 37787

Max Phase: Preclinical

Molecular Formula: C20H12O

Molecular Weight: 268.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-Hydroxybenzo[A]Pyrene | 4-Hydroxybenzo(a)pyrene|4-Hydroxybenzo[a]pyrene|37574-48-4|Benzo(a)pyren-4-ol|37IFC8W3E4|CHEBI:34420|Benz(a)pyrene, 4-hydroxy-|BENZO(a)PYRENE, 4-HYDROXY-|BRN 2464087|UNII-37IFC8W3E4|CHEMBL1908016|BENZO(PQR)TETRAPHEN-4-OL|DTXSID00191008|HYDROXYBENZO(A)PYRENE, 4-|Q27116054

Canonical SMILES:  Oc1cc2cc3ccccc3c3ccc4cccc1c4c23

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

Standard InChI Key:  URKORCVBWWKYKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 25  0  0  0  0  0  0  0  0999 V2000
  -11.8569    2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8570    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5714    3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2859    2.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2859    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5714    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1425    3.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4280    2.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4280    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1425    1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7135    3.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9990    2.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9990    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7135    1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1425    4.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4281    4.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7136    4.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9991    4.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2846    4.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2846    3.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2845    1.6698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  1  2  2  0
 10  1  1  0
  9 10  2  0
  9  8  1  0
 14  9  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
 20 12  2  0
 12 11  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 13 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1908016

   4-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: 9.33

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.96

Aromatic Rings: 5

Heavy Atoms: 21

QED Weighted: 0.29

Np Likeness Score: 0.47

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