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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:20:51 UTC

Update Date

2022-03-07 03:17:54 UTC

HMDB ID

HMDB0062438

Secondary Accession Numbers

HMDB62438

Metabolite Identification

Common Name

9-Hydroxybenzo[a]pyrene

Description

pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,5,7,9(19),10,12(20),13,15,17-decaen-4-ol 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. pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,5,7,9(19),10,12(20),13,15,17-decaen-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0062438
     RDKit          3D
9-Hydroxybenzo[a]pyrene
 33 37  0  0  0  0  0  0  0  0999 V2000
    5.0162   -2.0902   -0.0313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.0828   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5129    0.2148   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5588    1.2052   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077    0.9182   -0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    1.9122   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849    1.6713   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    2.6627   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930    2.4064    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279    1.1042    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1859    0.7897    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5954   -0.5187    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -1.5312    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -1.2134    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -2.2307    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0143   -1.9897    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -0.6817    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7475   -0.4066   -0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -1.3965    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098    0.3630    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    0.1004    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699   -2.5145   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676    0.4505   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    2.2274   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    2.9469   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797    3.7017   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094    3.2043   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8981    1.6078    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -0.7421    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -2.5570    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -3.2510    0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214   -2.8489    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362   -2.4319    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  2  0
 19  2  1  0
 18  5  1  0
 20  7  1  0
 21 10  1  0
 21 14  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
M  END


  Mrv1652303211707202D          

 21 25  0  0  0  0            999 V2000
   -1.7946    1.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    2.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758    3.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    4.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    4.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    4.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062438

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C=C1

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

> <INCHI_KEY>
OBBBXCAFTKLFGZ-UHFFFAOYSA-N

> <FORMULA>
C20H12O

> <MOLECULAR_WEIGHT>
268.315

> <EXACT_MASS>
268.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
30.143296567107974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,3,5,7,9(19),10,12(20),13,15,17-decaen-4-ol

> <ALOGPS_LOGP>
6.03

> <JCHEM_LOGP>
4.969838915666667

> <ALOGPS_LOGS>
-7.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.74660660469866

> <JCHEM_PKA_STRONGEST_BASIC>
-5.498706319928567

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
85.15370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,3,5,7,9(19),10,12(20),13,15,17-decaen-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0062438
     RDKit          3D
9-Hydroxybenzo[a]pyrene
 33 37  0  0  0  0  0  0  0  0999 V2000
    5.0162   -2.0902   -0.0313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.0828   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5129    0.2148   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5588    1.2052   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077    0.9182   -0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    1.9122   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849    1.6713   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    2.6627   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930    2.4064    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279    1.1042    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1859    0.7897    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5954   -0.5187    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -1.5312    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -1.2134    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -2.2307    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0143   -1.9897    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -0.6817    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7475   -0.4066   -0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -1.3965    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098    0.3630    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    0.1004    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699   -2.5145   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676    0.4505   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    2.2274   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    2.9469   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797    3.7017   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094    3.2043   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8981    1.6078    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -0.7421    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -2.5570    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -3.2510    0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214   -2.8489    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362   -2.4319    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  2  0
 19  2  1  0
 18  5  1  0
 20  7  1  0
 21 10  1  0
 21 14  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 21-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-17         0                                  
HETATM    1  O   UNK     0      -3.350   3.062   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.342   4.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.830   3.935   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.179   5.099   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.691   4.808   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.195   3.353   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.707   3.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.715   4.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.228   3.935   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.236   5.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.732   6.554   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.219   6.845   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.211   5.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.699   5.972   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.195   7.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.203   8.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.715   8.300   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.683   7.718   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.326   6.554   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.838   6.845   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.846   5.681   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0062438
HETATM    1  O1  UNL     1       5.016  -2.090  -0.031  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.066  -1.083  -0.041  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.513   0.215  -0.095  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.559   1.205  -0.103  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.208   0.918  -0.060  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.254   1.912  -0.069  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.085   1.671  -0.028  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.042   2.663  -0.037  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.393   2.406   0.006  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.828   1.104   0.059  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.186   0.790   0.104  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.595  -0.519   0.157  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.667  -1.531   0.167  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.302  -1.213   0.123  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.371  -2.231   0.133  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.014  -1.990   0.091  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.405  -0.682   0.038  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.747  -0.407  -0.005  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.701  -1.397   0.004  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.510   0.363   0.026  1.00  0.00           C  
HETATM   21  C20 UNL     1      -1.883   0.100   0.069  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.370  -2.514  -0.856  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.568   0.451  -0.129  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.917   2.227  -0.146  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.576   2.947  -0.111  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.680   3.702  -0.080  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.109   3.204  -0.003  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.898   1.608   0.094  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.639  -0.742   0.190  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.988  -2.557   0.209  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.767  -3.251   0.176  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.621  -2.849   0.104  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.436  -2.432   0.044  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3    3   19
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   18
CONECT    6    7    7   25
CONECT    7    8   20
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   11   21
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   21
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18   20
CONECT   18   19   19
CONECT   19   33
CONECT   20   21   21
END

HMDB0062438
     RDKit          3D
9-Hydroxybenzo[a]pyrene
 33 37  0  0  0  0  0  0  0  0999 V2000
    5.0162   -2.0902   -0.0313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.0828   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5129    0.2148   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5588    1.2052   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077    0.9182   -0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    1.9122   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849    1.6713   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    2.6627   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930    2.4064    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279    1.1042    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1859    0.7897    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5954   -0.5187    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -1.5312    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -1.2134    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -2.2307    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0143   -1.9897    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -0.6817    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7475   -0.4066   -0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -1.3965    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098    0.3630    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    0.1004    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699   -2.5145   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676    0.4505   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    2.2274   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    2.9469   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797    3.7017   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094    3.2043   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8981    1.6078    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -0.7421    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -2.5570    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -3.2510    0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214   -2.8489    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362   -2.4319    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  2  0
 19  2  1  0
 18  5  1  0
 20  7  1  0
 21 10  1  0
 21 14  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
benzo[Def]chrysen-9-ol	ChEMBL, HMDB
9-hydroxybenzo(a)Pyrene, 3H-labeled	HMDB

Chemical Formula

C₂₀H₁₂O

Average Molecular Weight

268.315

Monoisotopic Molecular Weight

268.088815006

IUPAC Name

pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,3,5,7,9(19),10,12(20),13,15,17-decaen-4-ol

Traditional Name

pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1,3,5,7,9(19),10,12(20),13,15,17-decaen-4-ol

CAS Registry Number

17573-21-6

SMILES

OC1=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C=C1

InChI Identifier

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

InChI Key

OBBBXCAFTKLFGZ-UHFFFAOYSA-N

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-a-pyrene
Chrysene
Phenanthrol
Phenanthrene
Anthracene
2-naphthol
1-hydroxy-2-unsubstituted benzenoid
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ortho- and peri-fused polycyclic arene (CHEBI:34512 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.9e-05 g/l	ALOGPS
LogP	6.03	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.03	ALOGPS
logP	4.97	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.15 m³·mol⁻¹	ChemAxon
Polarizability	30.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.496	31661259
DarkChem	[M-H]-	161.48	31661259
DeepCCS	[M+H]+	177.038	30932474
DeepCCS	[M-H]-	174.68	30932474
DeepCCS	[M-2H]-	208.36	30932474
DeepCCS	[M+Na]+	183.587	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	167.9	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxybenzo[a]pyrene	OC1=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C=C1	4384.7	Standard polar	33892256
9-Hydroxybenzo[a]pyrene	OC1=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C=C1	3064.7	Standard non polar	33892256
9-Hydroxybenzo[a]pyrene	OC1=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C=C1	3308.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxybenzo[a]pyrene,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=C3C=CC4=CC=CC5=CC=C(C2=C1)C3=C45	3222.0	Semi standard non polar	33892256
9-Hydroxybenzo[a]pyrene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=C3C=CC4=CC=CC5=CC=C(C2=C1)C3=C45	3367.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxybenzo[a]pyrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0090000000-9220f112be577f77e05a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxybenzo[a]pyrene GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9076000000-dac4a2b652c42f3bfbb7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxybenzo[a]pyrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 10V, Positive-QTOF	splash10-014i-0090000000-0cf12d92bb15b8d16f01	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 20V, Positive-QTOF	splash10-014i-0090000000-c29c2450f7dfa49ed2b8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 40V, Positive-QTOF	splash10-00p3-0090000000-1aedbcc7561b9de5055a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 10V, Negative-QTOF	splash10-014i-0090000000-277a3dc3bfbdd0da4e77	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 20V, Negative-QTOF	splash10-014i-0090000000-a6338779f141ca32d279	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 40V, Negative-QTOF	splash10-014i-0090000000-040d50e7e32b9f8202a9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 10V, Negative-QTOF	splash10-014i-0090000000-15826f0c2063c7e25e62	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 20V, Negative-QTOF	splash10-014i-0090000000-15826f0c2063c7e25e62	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 40V, Negative-QTOF	splash10-014i-0090000000-92d898667315fc950eab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 10V, Positive-QTOF	splash10-014i-0090000000-d6caa442c8b0b02a8eb5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 20V, Positive-QTOF	splash10-014i-0090000000-d6caa442c8b0b02a8eb5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene 40V, Positive-QTOF	splash10-014i-0090000000-c1b5888e2742a325a90e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14556

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

28598

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

M01241

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 9-Hydroxybenzo[a]pyrene (HMDB0062438)

MOL for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

3D MOL for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

3D SDF for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

3D-SDF for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

PDB for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

3D PDB for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

SMILES for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

INCHI for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

Structure for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

3D Structure for HMDB0062438 (9-Hydroxybenzo[a]pyrene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra