Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:27:42 UTC

Update Date

2021-09-26 22:59:35 UTC

HMDB ID

HMDB0248998

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Hydroxybenzo(a)pyrene

Description

benzo[a]pyren-3-ol, also known as 3-OH-BP, 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. benzo[a]pyren-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-hydroxybenzo(a)pyrene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Hydroxybenzo(a)pyrene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248998
     RDKit          3D
3-Hydroxybenzo(a)pyrene
 33 37  0  0  0  0  0  0  0  0999 V2000
   -4.7442    1.7620    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    0.7667    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -0.5255   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.5470   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -1.3118   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -2.3627   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.1576   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031   -0.8837   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0845   -0.6553   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -1.6684   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3425   -1.3712   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7837   -0.0953   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706    0.9007    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202    0.6491    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6221    1.6479    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609    1.4456    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135    2.5008    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    2.2630    0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    1.0105    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.0267   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941    0.1714    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625    2.7190    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3117   -0.7302   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912   -2.5703   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.3311   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -3.0193   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -2.6573   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0446   -2.1794   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8469    0.1225    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    1.9129    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    2.6505    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    3.4812    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467    3.0888    0.6285 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
 19 20  1  0
 20 21  2  0
 19  2  1  0
 20  5  1  0
 21  8  1  0
 14  9  1  0
 21 16  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1533005011514002D          

 21 25  0  0  0  0            999 V2000
    0.3488    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  2 19  2  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248998

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C2C=CC3=CC4=CC=CC=C4C4=CC=C(C=C1)C2=C34

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

> <INCHI_KEY>
SPUUWWRWIAEPDB-UHFFFAOYSA-N

> <FORMULA>
C20H12O

> <MOLECULAR_WEIGHT>
268.315

> <EXACT_MASS>
268.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
30.08543168309282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-13-ol

> <ALOGPS_LOGP>
5.93

> <JCHEM_LOGP>
4.969838915666667

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495977983612875

> <JCHEM_PKA_STRONGEST_BASIC>
-5.599871443477395

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
85.15369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxybenzo(a)pyrene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248998
     RDKit          3D
3-Hydroxybenzo(a)pyrene
 33 37  0  0  0  0  0  0  0  0999 V2000
   -4.7442    1.7620    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    0.7667    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -0.5255   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.5470   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -1.3118   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -2.3627   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.1576   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031   -0.8837   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0845   -0.6553   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -1.6684   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3425   -1.3712   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7837   -0.0953   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706    0.9007    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202    0.6491    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6221    1.6479    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609    1.4456    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135    2.5008    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    2.2630    0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    1.0105    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.0267   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941    0.1714    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625    2.7190    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3117   -0.7302   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912   -2.5703   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.3311   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -3.0193   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -2.6573   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0446   -2.1794   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8469    0.1225    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    1.9129    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    2.6505    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    3.4812    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467    3.0888    0.6285 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
 19 20  1  0
 20 21  2  0
 19  2  1  0
 20  5  1  0
 21  8  1  0
 14  9  1  0
 21 16  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  O   UNK     0       0.651   0.752   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.659   1.916   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.155   3.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.163   4.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.676   4.244   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.684   5.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.196   5.117   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.700   3.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.212   3.371   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.220   4.535   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.733   4.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.237   2.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.229   1.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.716   1.916   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.708   0.752   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.196   1.043   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.188  -0.121   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.676   0.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.171   1.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.180   2.789   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.692   2.498   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19    5   21                                                  
CONECT   21   20    8   16                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0248998
HETATM    1  O1  UNL     1      -4.744   1.762   0.366  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.829   0.767   0.164  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.250  -0.525  -0.096  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.360  -1.547  -0.304  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.002  -1.312  -0.259  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.103  -2.363  -0.473  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.258  -2.158  -0.435  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.703  -0.884  -0.180  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.084  -0.655  -0.137  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.982  -1.668  -0.343  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.343  -1.371  -0.287  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.784  -0.095  -0.031  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.871   0.901   0.172  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.520   0.649   0.125  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.622   1.648   0.328  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.261   1.446   0.291  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.614   2.501   0.505  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.966   2.263   0.461  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.475   1.011   0.209  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.573  -0.027  -0.002  1.00  0.00           C  
HETATM   21  C20 UNL     1      -0.194   0.171   0.035  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.563   2.719   0.559  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.312  -0.730  -0.134  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.691  -2.570  -0.509  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.519  -3.331  -0.667  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.870  -3.019  -0.610  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.641  -2.657  -0.542  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.045  -2.179  -0.451  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.847   0.122   0.011  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.216   1.913   0.375  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.995   2.650   0.529  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.200   3.481   0.702  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.647   3.089   0.629  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   20
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   21
CONECT    9   10   14
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15
CONECT   15   16   31
CONECT   16   17   17   21
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20
CONECT   20   21   21
END

HMDB0248998
     RDKit          3D
3-Hydroxybenzo(a)pyrene
 33 37  0  0  0  0  0  0  0  0999 V2000
   -4.7442    1.7620    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    0.7667    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -0.5255   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.5470   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -1.3118   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -2.3627   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -2.1576   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031   -0.8837   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0845   -0.6553   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -1.6684   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3425   -1.3712   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7837   -0.0953   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706    0.9007    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202    0.6491    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6221    1.6479    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609    1.4456    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135    2.5008    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    2.2630    0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    1.0105    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.0267   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941    0.1714    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625    2.7190    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3117   -0.7302   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912   -2.5703   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.3311   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -3.0193   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -2.6573   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0446   -2.1794   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8469    0.1225    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    1.9129    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    2.6505    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    3.4812    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467    3.0888    0.6285 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
 19 20  1  0
 20 21  2  0
 19  2  1  0
 20  5  1  0
 21  8  1  0
 14  9  1  0
 21 16  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-OH-BP	MeSH
3-OH-BaP	MeSH
3-Hydroxybenzo(a)pyrene	MeSH
3-Hydroxybenzo(a)pyrene, 3H-labeled	MeSH
Benzo(a)pyren-3-ol	MeSH
benzo[Def]chrysen-3-ol	ChEMBL

Chemical Formula

C₂₀H₁₂O

Average Molecular Weight

268.315

Monoisotopic Molecular Weight

268.088815006

IUPAC Name

pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-13-ol

Traditional Name

3-hydroxybenzo(a)pyrene

CAS Registry Number

Not Available

SMILES

OC1=C2C=CC3=CC4=CC=CC=C4C4=CC=C(C=C1)C2=C34

InChI Identifier

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

InChI Key

SPUUWWRWIAEPDB-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
1-naphthol
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:34337 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.93	ALOGPS
logP	4.97	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-5.6	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	30.09 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
DeepCCS	[M-2H]-	198.786	30932474
DeepCCS	[M+Na]+	174.013	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.4	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
3-Hydroxybenzo(a)pyrene	OC1=C2C=CC3=CC4=CC=CC=C4C4=CC=C(C=C1)C2=C34	4224.6	Standard polar	33892256
3-Hydroxybenzo(a)pyrene	OC1=C2C=CC3=CC4=CC=CC=C4C4=CC=C(C=C1)C2=C34	3034.2	Standard non polar	33892256
3-Hydroxybenzo(a)pyrene	OC1=C2C=CC3=CC4=CC=CC=C4C4=CC=C(C=C1)C2=C34	3278.2	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 - 3-Hydroxybenzo(a)pyrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0090000000-fc920fb0d019639d3ee4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxybenzo(a)pyrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxybenzo(a)pyrene GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxybenzo(a)pyrene GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 35V, Negative-QTOF	splash10-014i-0090000000-4b4121d82c1e7213ab73	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 35V, Positive-QTOF	splash10-0udi-0090000000-7b2861a3ccf26d542878	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 10V, Positive-QTOF	splash10-014i-0090000000-0a9b3c77d60ab7fdc8b2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 20V, Positive-QTOF	splash10-014i-0090000000-e067bdb7985157f0bc61	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 40V, Positive-QTOF	splash10-014l-0090000000-015b4663e7c4db65a32f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 10V, Negative-QTOF	splash10-014i-0090000000-df75e037c94cb35e2c50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 20V, Negative-QTOF	splash10-014i-0090000000-df75e037c94cb35e2c50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 40V, Negative-QTOF	splash10-014i-0090000000-d130faab5da87fb55f4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 10V, Negative-QTOF	splash10-014i-0090000000-15826f0c2063c7e25e62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 20V, Negative-QTOF	splash10-014i-0090000000-15826f0c2063c7e25e62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 40V, Negative-QTOF	splash10-014r-0090000000-2c4dbc628c272e22903a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 10V, Positive-QTOF	splash10-014i-0090000000-d6caa442c8b0b02a8eb5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 20V, Positive-QTOF	splash10-014i-0090000000-d6caa442c8b0b02a8eb5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybenzo(a)pyrene 40V, Positive-QTOF	splash10-014r-0090000000-e66724ffe8f7f4047186	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

C14461

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25890

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3-Hydroxybenzo(a)pyrene (HMDB0248998)

MOL for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

3D MOL for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

3D SDF for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

3D-SDF for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

PDB for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

3D PDB for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

SMILES for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

INCHI for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

Structure for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

3D Structure for HMDB0248998 (3-Hydroxybenzo(a)pyrene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra