NP-MRD: Showing NP-Card for 9-hydroxybenzo(a)pyrene (NP0287287)

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Record Information

Version

2.0

Created at

2022-09-09 16:16:55 UTC

Updated at

2022-09-09 16:16:56 UTC

NP-MRD ID

NP0287287

Secondary Accession Numbers

None

Natural Product 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. 9-hydroxybenzo(a)pyrene is found in Mus musculus. 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 PDB SMILES InChI

     RDKit          3D

 33 37  0  0  0  0  0  0  0  0999 V2000
   -5.0391    2.0179   -0.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1172    0.9929    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4649   -0.3260    0.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4684   -1.2932    0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343   -0.9591    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502   -1.9095    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927   -1.6139    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -2.6308    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4722   -2.3240    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8796   -1.0145    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2236   -0.7093   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    0.6066   -0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465    1.6147   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2894    1.3147   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    2.2896   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    2.0241   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118    0.7007   -0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715    0.3900    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.3414   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -0.2984    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0055   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0267    1.8989   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5225   -0.5929    0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7876   -2.3252    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160   -2.9674    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7884   -3.6405    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893   -3.1313    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291   -1.5279    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    0.8588   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    2.6569   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238    3.3269   -0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326    2.8624   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5145    2.3730   -0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10 21  1  0
 21 20  2  0
 20  7  1  0
  7  8  2  0
  8  9  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  5 18  1  0
 20 17  1  0
 21 14  1  0
  9 10  2  0
  1 22  1  0
 19 33  1  0
 16 32  1  0
 15 31  1  0
 13 30  1  0
 12 29  1  0
 11 28  1  0
  8 26  1  0
  9 27  1  0
  6 25  1  0
  4 24  1  0
  3 23  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>
NP0287287

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

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

Chemical Formula

C₂₀H₁₂O

Average Mass

268.3150 Da

Monoisotopic Mass

268.08882 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0062438

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-hydroxybenzo(a)pyrene (NP0287287)

MOL for NP0287287 (9-hydroxybenzo(a)pyrene)

3D MOL for NP0287287 (9-hydroxybenzo(a)pyrene)

3D SDF for NP0287287 (9-hydroxybenzo(a)pyrene)

3D-SDF for NP0287287 (9-hydroxybenzo(a)pyrene)

PDB for NP0287287 (9-hydroxybenzo(a)pyrene)

3D PDB for NP0287287 (9-hydroxybenzo(a)pyrene)

SMILES for NP0287287 (9-hydroxybenzo(a)pyrene)

INCHI for NP0287287 (9-hydroxybenzo(a)pyrene)

Structure for NP0287287 (9-hydroxybenzo(a)pyrene)

3D Structure for NP0287287 (9-hydroxybenzo(a)pyrene)