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Showing NP-Card for 16-alpha-Hydroxyandrosterone (NP0339198)

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Record Information
Version2.0
Created at2024-09-11 20:21:35 UTC
Updated at2024-09-11 20:21:35 UTC
NP-MRD IDNP0339198
Secondary Accession NumbersNone
Natural Product Identification
Common Name16-alpha-Hydroxyandrosterone
Description1-Hydroxypyrene, also known as 1-pyrenol or pyren-1-ol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. 1-Hydroxypyrene is an extremely weak basic (essentially neutral) compound (based on its pKa). 16-alpha-Hydroxyandrosterone was first documented in 2004 (PMID: 15159317). 1-Hydroxypyrene is a potentially toxic compound (PMID: 15247141).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339198 (16-alpha-Hydroxyandrosterone)


  Mrv0541 02251208172D          

 22 25  0  0  1  0            999 V2000
    5.0979  -13.1950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0979  -14.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834  -12.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834  -14.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690  -13.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690  -14.0200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5269  -13.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269  -14.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124  -12.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124  -14.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2415  -11.9575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2415  -12.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269  -11.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125  -11.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0260  -11.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110  -12.3700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0261  -13.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0979  -12.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277  -11.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2810  -10.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9545  -14.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3360  -12.3700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  1 18  1  1  0  0  0
 11 19  1  1  0  0  0
 20 15  2  0  0  0  0
  6 21  1  6  0  0  0
 16 22  1  6  0  0  0
M  END
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3D MOL for NP0339198 (16-alpha-Hydroxyandrosterone)

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3D SDF for NP0339198 (16-alpha-Hydroxyandrosterone)

  Mrv0541 02251208172D          

 22 25  0  0  1  0            999 V2000
    5.0979  -13.1950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0979  -14.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834  -12.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834  -14.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690  -13.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690  -14.0200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5269  -13.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269  -14.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124  -12.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124  -14.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2415  -11.9575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2415  -12.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269  -11.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125  -11.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0260  -11.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110  -12.3700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0261  -13.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0979  -12.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277  -11.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2810  -10.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9545  -14.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3360  -12.3700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  1 18  1  1  0  0  0
 11 19  1  1  0  0  0
 20 15  2  0  0  0  0
  6 21  1  6  0  0  0
 16 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0339198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1C[C@@H](O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h11-16,20-21H,3-10H2,1-2H3/t11?,12-,13?,14?,15?,16-,18+,19+/m1/s1

> <INCHI_KEY>
HLQYTKUIIJTNHH-LIEJGXIJSA-N

> <FORMULA>
C19H30O3

> <MOLECULAR_WEIGHT>
306.4397

> <EXACT_MASS>
306.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.31926516028542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.896218616

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.296396321120493

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.382232174468555

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569561658047151

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
85.30109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339198 (16-alpha-Hydroxyandrosterone)
Download
PDB for NP0339198 (16-alpha-Hydroxyandrosterone)
HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0       9.516 -24.631   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.516 -26.171   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.182 -23.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.182 -26.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.849 -24.631   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.849 -26.171   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.184 -24.631   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.184 -26.171   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.850 -23.861   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.850 -26.941   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.517 -22.321   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.517 -23.861   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.184 -21.551   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.850 -22.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.982 -21.845   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.887 -23.091   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.982 -24.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.516 -23.091   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.678 -20.789   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.458 -20.380   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.515 -26.941   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      17.427 -23.091   0.000  0.00  0.00           O+0
CONECT    1    3    9    2   18                                             
CONECT    2    4   10    1                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   21                                                  
CONECT    7    8   12    9                                                  
CONECT    8    7   10                                                       
CONECT    9    1    7   14                                                  
CONECT   10    8    2                                                       
CONECT   11   13   15   12   19                                             
CONECT   12    7   11   17                                                  
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   20                                                  
CONECT   16   15   17   22                                                  
CONECT   17   12   16                                                       
CONECT   18    1                                                            
CONECT   19   11                                                            
CONECT   20   15                                                            
CONECT   21    6                                                            
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

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3D PDB for NP0339198 (16-alpha-Hydroxyandrosterone)
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SMILES for NP0339198 (16-alpha-Hydroxyandrosterone)
C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1C[C@@H](O)C2=O
Download
INCHI for NP0339198 (16-alpha-Hydroxyandrosterone)
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h11-16,20-21H,3-10H2,1-2H3/t11?,12-,13?,14?,15?,16-,18+,19+/m1/s1
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View in JSmol
Synonyms
ValueSource
1-Hydroxy pyreneHMDB
1-PyrenolHMDB
Pyren-1-olHMDB
16-a-HydroxyandrosteroneGenerator
16-Α-hydroxyandrosteroneGenerator
Chemical FormulaC19H30O3
Average Mass306.4397 Da
Monoisotopic Mass306.21949 Da
IUPAC Name(2S,5R,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
Traditional Name(2S,5R,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
CAS Registry NumberNot Available
SMILES
C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1C[C@@H](O)C2=O
InChI Identifier
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h11-16,20-21H,3-10H2,1-2H3/t11?,12-,13?,14?,15?,16-,18+,19+/m1/s1
InChI KeyHLQYTKUIIJTNHH-LIEJGXIJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenanthrenes and derivatives  
Sub ClassPhenanthrols  
Direct ParentPhenanthrols  
Alternative Parents
Substituents
  • Phenanthrol
    • 

  • Phenalen
    • 

  • Naphthalene
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.82ALOGPS
logP2.9ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.3 m³·mol⁻¹ChemAxon
Polarizability35.32 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013139  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029309  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14519  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Hydroxypyrene  
METLIN IDNot Available
PubChem Compound53481631  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hecht SS, Carmella SG, Le KA, Murphy SE, Li YS, Le C, Jensen J, Hatsukami DK: Effects of reduced cigarette smoking on levels of 1-hydroxypyrene in urine. Cancer Epidemiol Biomarkers Prev. 2004 May;13(5):834-42. [PubMed:15159317  ] 
  2. Carmella SG, Le KA, Hecht SS: Improved method for determination of 1-hydroxypyrene in human urine. Cancer Epidemiol Biomarkers Prev. 2004 Jul;13(7):1261-4. [PubMed:15247141  ]