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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:20:56 UTC

Update Date

2022-03-07 03:17:54 UTC

HMDB ID

HMDB0062439

Secondary Accession Numbers

HMDB62439

Metabolite Identification

Common Name

9-Hydroxybenzo[a]pyrene-4,5-oxide

Description

18-oxahexacyclo[10.7.2.0³,⁸.0⁹,²⁰.0¹⁶,²¹.0¹⁷,¹⁹]henicosa-1(20),2,4,6,8,10,12(21),13,15-nonaen-6-ol, also known as 9-hydroxybenzo[a]pyrene-4,5-epoxide, belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. 18-oxahexacyclo[10.7.2.0³,⁸.0⁹,²⁰.0¹⁶,²¹.0¹⁷,¹⁹]henicosa-1(20),2,4,6,8,10,12(21),13,15-nonaen-6-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

HMDB0062439
     RDKit          3D
9-Hydroxybenzo[a]pyrene-4,5-oxide
 34 39  0  0  0  0  0  0  0  0999 V2000
    4.3344    0.1949   -3.3867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.4474   -2.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019    1.0861   -1.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    1.2763    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401    0.8590    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    1.0563    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1984    0.6529    1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.0144    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2078   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -0.8353   -1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5893   -1.2316   -1.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.0174   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202   -1.4438   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3422   -1.2483    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -0.6256    1.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -0.1950    1.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7384   -0.3932    0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    0.4385    2.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890    1.8544    2.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266    0.9515    2.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6232    0.2083   -0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591    0.0128   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -0.6483   -3.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    1.4067   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017    1.7780    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599    1.5551    2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997   -1.0411   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954   -1.7360   -2.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482   -1.9376   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654   -1.5772    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845   -0.4453    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396    0.1797    3.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    1.0896    3.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241   -0.4783   -2.9351 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
 16 18  1  0
 18 19  1  0
 19 20  1  0
  9 21  1  0
 21 22  2  0
 22  2  1  0
 21  5  1  0
 20  7  1  0
 17  8  1  0
 20 18  1  0
 17 12  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 20 33  1  0
 22 34  1  0
M  END


  Mrv1652303211707202D          

 22 27  0  0  0  0            999 V2000
    2.4922    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -1.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    0.1007    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
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 17 22  2  0  0  0  0
  5 22  1  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062439

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C3C=CC4=C5C(=CC=C4)C4OC4C(C=C2C=C1)=C35

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O2/c21-12-6-4-11-8-16-18-13(15(11)9-12)7-5-10-2-1-3-14(17(10)18)19-20(16)22-19/h1-9,19-21H

> <INCHI_KEY>
QMJJLPWCBGOGAF-UHFFFAOYSA-N

> <FORMULA>
C20H12O2

> <MOLECULAR_WEIGHT>
284.314

> <EXACT_MASS>
284.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.885694181580398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
18-oxahexacyclo[10.7.2.0^{3,8}.0^{9,20}.0^{16,21}.0^{17,19}]henicosa-1(20),2,4,6,8,10,12(21),13,15-nonaen-6-ol

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.213123998666666

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.74691419368544

> <JCHEM_PKA_STRONGEST_BASIC>
-4.271506924825497

> <JCHEM_POLAR_SURFACE_AREA>
32.76

> <JCHEM_REFRACTIVITY>
84.88260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-oxahexacyclo[10.7.2.0^{3,8}.0^{9,20}.0^{16,21}.0^{17,19}]henicosa-1(20),2,4,6,8,10,12(21),13,15-nonaen-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0062439
     RDKit          3D
9-Hydroxybenzo[a]pyrene-4,5-oxide
 34 39  0  0  0  0  0  0  0  0999 V2000
    4.3344    0.1949   -3.3867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.4474   -2.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019    1.0861   -1.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    1.2763    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401    0.8590    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    1.0563    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1984    0.6529    1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.0144    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2078   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -0.8353   -1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5893   -1.2316   -1.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.0174   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202   -1.4438   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3422   -1.2483    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -0.6256    1.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -0.1950    1.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7384   -0.3932    0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    0.4385    2.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890    1.8544    2.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266    0.9515    2.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6232    0.2083   -0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591    0.0128   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -0.6483   -3.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    1.4067   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017    1.7780    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599    1.5551    2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997   -1.0411   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954   -1.7360   -2.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482   -1.9376   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654   -1.5772    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845   -0.4453    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396    0.1797    3.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    1.0896    3.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241   -0.4783   -2.9351 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
 16 18  1  0
 18 19  1  0
 19 20  1  0
  9 21  1  0
 21 22  2  0
 22  2  1  0
 21  5  1  0
 20  7  1  0
 17  8  1  0
 20 18  1  0
 17 12  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 20 33  1  0
 22 34  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       4.652   3.098   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.660   1.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.172   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.181   1.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.693   1.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.197   2.807   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.709   3.098   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.717   1.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.213   0.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.221  -0.685   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.734  -0.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.238   1.061   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.230   2.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.717  -2.140   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.213  -3.595   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.205  -2.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.197  -1.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.685  -1.558   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.677  -0.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.164  -0.685   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.156   0.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.701   0.188   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   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   10   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    2                                                       
CONECT   22   17    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   54    0
END

COMPND    HMDB0062439
HETATM    1  O1  UNL     1       4.334   0.195  -3.387  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.693   0.447  -2.187  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.302   1.086  -1.130  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.552   1.276   0.010  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.240   0.859   0.128  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.507   1.056   1.269  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.198   0.653   1.419  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.408   0.014   0.365  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.309  -0.208  -0.827  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.278  -0.835  -1.901  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.589  -1.232  -1.751  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.299  -1.017  -0.581  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.620  -1.444  -0.480  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.342  -1.248   0.674  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.771  -0.626   1.755  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.452  -0.195   1.667  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.738  -0.393   0.508  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.840   0.439   2.838  1.00  0.00           C  
HETATM   19  O2  UNL     1      -1.589   1.854   2.621  1.00  0.00           O  
HETATM   20  C18 UNL     1      -0.527   0.951   2.710  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.623   0.208  -0.953  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.359   0.013  -2.093  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.860  -0.648  -3.585  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.323   1.407  -1.232  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.002   1.778   0.866  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.960   1.555   2.114  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.200  -1.041  -2.843  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.095  -1.736  -2.586  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.048  -1.938  -1.359  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.365  -1.577   0.754  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.284  -0.445   2.683  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.240   0.180   3.837  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.101   1.090   3.612  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.924  -0.478  -2.935  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3    3   22
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   21
CONECT    6    7    7   26
CONECT    7    8   20
CONECT    8    9    9   17
CONECT    9   10   21
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   17
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   31
CONECT   16   17   17   18
CONECT   18   19   20   32
CONECT   19   20
CONECT   20   33
CONECT   21   22   22
CONECT   22   34
END

HMDB0062439
     RDKit          3D
9-Hydroxybenzo[a]pyrene-4,5-oxide
 34 39  0  0  0  0  0  0  0  0999 V2000
    4.3344    0.1949   -3.3867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.4474   -2.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019    1.0861   -1.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    1.2763    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401    0.8590    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    1.0563    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1984    0.6529    1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.0144    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2078   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -0.8353   -1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5893   -1.2316   -1.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.0174   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202   -1.4438   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3422   -1.2483    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -0.6256    1.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -0.1950    1.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7384   -0.3932    0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    0.4385    2.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890    1.8544    2.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266    0.9515    2.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6232    0.2083   -0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591    0.0128   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -0.6483   -3.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    1.4067   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017    1.7780    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599    1.5551    2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997   -1.0411   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954   -1.7360   -2.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482   -1.9376   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654   -1.5772    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845   -0.4453    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396    0.1797    3.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    1.0896    3.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241   -0.4783   -2.9351 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
 16 18  1  0
 18 19  1  0
 19 20  1  0
  9 21  1  0
 21 22  2  0
 22  2  1  0
 21  5  1  0
 20  7  1  0
 17  8  1  0
 20 18  1  0
 17 12  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Hydroxybenzo[a]pyrene-4,5-epoxide	Kegg
9-hydroxybenzo(a)Pyrene-4,5-epoxide	HMDB
9-hydroxybenzo(a)Pyrene-4,5-oxide	HMDB
9-OH-BaP-4,5-oxide	HMDB

Chemical Formula

C₂₀H₁₂O₂

Average Molecular Weight

284.314

Monoisotopic Molecular Weight

284.083729626

IUPAC Name

18-oxahexacyclo[10.7.2.0^{3,8}.0^{9,20}.0^{16,21}.0^{17,19}]henicosa-1(20),2,4,6,8,10,12(21),13,15-nonaen-6-ol

Traditional Name

18-oxahexacyclo[10.7.2.0^{3,8}.0^{9,20}.0^{16,21}.0^{17,19}]henicosa-1(20),2,4,6,8,10,12(21),13,15-nonaen-6-ol

CAS Registry Number

61133-85-5

SMILES

OC1=CC2=C3C=CC4=C5C(=CC=C4)C4OC4C(C=C2C=C1)=C35

InChI Identifier

InChI=1S/C20H12O2/c21-12-6-4-11-8-16-18-13(15(11)9-12)7-5-10-2-1-3-14(17(10)18)19-20(16)22-19/h1-9,19-21H

InChI Key

QMJJLPWCBGOGAF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Chrysenes

Direct Parent

Chrysenes

Alternative Parents

Substituents

Chrysene
Phenanthrol
2-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbopolycyclic compound (CHEBI:34513 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062439)

Process

Not Available

Role

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	0.00035 g/l	ALOGPS
LogP	4.62	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.62	ALOGPS
logP	4.21	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.88 m³·mol⁻¹	ChemAxon
Polarizability	30.89 Å³	ChemAxon
Number of Rings	6	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]+	163.133	31661259
DarkChem	[M-H]-	165.544	31661259
DeepCCS	[M-2H]-	208.181	30932474
DeepCCS	[M+Na]+	183.408	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.4	32859911
AllCCS	[M+Na]+	172.3	32859911
AllCCS	[M-H]-	174.1	32859911
AllCCS	[M+Na-2H]-	172.6	32859911
AllCCS	[M+HCOO]-	171.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	6.68 minutes	32390414
Predicted by Siyang on May 30, 2022	17.8872 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2522.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	578.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	244.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	332.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	471.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	823.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	710.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1303.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	711.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1889.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	537.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	544.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	297.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxybenzo[a]pyrene-4,5-oxide	OC1=CC2=C3C=CC4=C5C(=CC=C4)C4OC4C(C=C2C=C1)=C35	4282.4	Standard polar	33892256
9-Hydroxybenzo[a]pyrene-4,5-oxide	OC1=CC2=C3C=CC4=C5C(=CC=C4)C4OC4C(C=C2C=C1)=C35	2921.9	Standard non polar	33892256
9-Hydroxybenzo[a]pyrene-4,5-oxide	OC1=CC2=C3C=CC4=C5C(=CC=C4)C4OC4C(C=C2C=C1)=C35	3383.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxybenzo[a]pyrene-4,5-oxide,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=C3C4=C(C=CC5=CC=CC(=C54)C4OC34)C2=C1	3276.2	Semi standard non polar	33892256
9-Hydroxybenzo[a]pyrene-4,5-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=C3C4=C(C=CC5=CC=CC(=C54)C4OC34)C2=C1	3427.4	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-4,5-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-0190000000-e28606225006b285cdaa	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-00ec-8098000000-92d0140a4881202eafc7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 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-4,5-oxide 10V, Positive-QTOF	splash10-000i-0090000000-527b811941a55a8d03fc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 20V, Positive-QTOF	splash10-000i-0090000000-8042deaaf94df62a0120	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 40V, Positive-QTOF	splash10-05mo-1090000000-4de25e0158927a0fd20d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 10V, Negative-QTOF	splash10-001i-0090000000-b103dd17722f883f72cc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 20V, Negative-QTOF	splash10-001i-0090000000-1c63f8983338e170daee	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 40V, Negative-QTOF	splash10-053r-0090000000-3104004ef809281907ed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 10V, Negative-QTOF	splash10-001i-0090000000-99f11c209da1d005ec5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 20V, Negative-QTOF	splash10-001i-0090000000-99f11c209da1d005ec5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 40V, Negative-QTOF	splash10-001i-0090000000-16c6c0152b501ea0e23b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 10V, Positive-QTOF	splash10-000i-0090000000-6d53c52d4ba653ff9df5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 20V, Positive-QTOF	splash10-000i-0090000000-6d53c52d4ba653ff9df5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxybenzo[a]pyrene-4,5-oxide 40V, Positive-QTOF	splash10-000i-0090000000-55c1347b061eff29d2ae	2021-09-25	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

C14854

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115064

PDB ID

Not Available

ChEBI ID

34513

Food Biomarker Ontology

Not Available

VMH ID

M01242

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-4,5-oxide (HMDB0062439)

MOL for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

3D MOL for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

3D SDF for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

3D-SDF for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

PDB for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

3D PDB for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

SMILES for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

INCHI for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

Structure for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

3D Structure for HMDB0062439 (9-Hydroxybenzo[a]pyrene-4,5-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra