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Showing NP-Card for Norbolethone (NP0334747)

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Record Information
Version2.0
Created at2024-09-10 19:47:36 UTC
Updated at2024-09-10 19:47:37 UTC
NP-MRD IDNP0334747
Secondary Accession NumbersNone
Natural Product Identification
Common NameNorbolethone
DescriptionNorbolethone, also known as 13-ehdpo or genabol, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. It is reputed to have been the active ingredient in the original formulation of the "undetectable" steroid formulation known as "The Clear" before being replaced by the more potent drug tetrahydrogestrinone. Norbolethone is an extremely weak basic (essentially neutral) compound (based on its pKa). Norboletone (INN) (former proposed brand name Genabol), or norbolethone, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed. The following year, Catlin identified and developed a test for tetrahydrogestrinone (THG), the second reported designer anabolic sample—a key development in the BALCO Affair. In the same year, U.S. Bicycle racer Tammy Thomas was caught using it and was banned from her sport. Norboletone is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports. In 2002, Don Catlin, the founder and then-director of the UCLA Olympic Analytical Lab, identified norboletone for the first time in an athlete's urine sample. It was first developed in 1966 by Wyeth Laboratories and was investigated for use as an agent to encourage weight gain and for the treatment of short stature, but was never marketed commercially because of fears that it might be toxic. Norbolethone was first documented in 2002 (PMID: 12112254). It subsequently showed up in urine tests on athletes in competition in the early 2000s.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334747 (Norbolethone)


  Mrv0541 02231220322D          

 27 30  0  0  1  0            999 V2000
   20.2787   -4.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -7.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8298   -4.9493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8298   -5.7743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1155   -6.1868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6105   -4.6980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4009   -5.7743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1155   -4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6105   -6.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4009   -4.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0919   -5.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6503   -6.1925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.8298   -4.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1287   -7.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3570   -3.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3878   -7.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6437   -7.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8857   -5.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1155   -3.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9099   -3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1037   -6.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8720   -7.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0968   -7.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8997   -6.6368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.1395   -5.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3814   -6.5442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6630   -5.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  2 23  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  3 13  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 24  1  6  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  5 25  1  1  0  0  0
  6 11  1  0  0  0  0
  6 15  1  6  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 26  1  6  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 12 27  1  1  0  0  0
 13 19  1  0  0  0  0
 14 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 22  2  0  0  0  0
 18 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
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3D MOL for NP0334747 (Norbolethone)

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3D SDF for NP0334747 (Norbolethone)

  Mrv0541 02231220322D          

 27 30  0  0  1  0            999 V2000
   20.2787   -4.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -7.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8298   -4.9493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8298   -5.7743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1155   -6.1868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6105   -4.6980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4009   -5.7743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1155   -4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6105   -6.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4009   -4.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0919   -5.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6503   -6.1925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.8298   -4.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1287   -7.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3570   -3.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3878   -7.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6437   -7.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8857   -5.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1155   -3.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9099   -3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1037   -6.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8720   -7.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0968   -7.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8997   -6.6368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.1395   -5.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3814   -6.5442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6630   -5.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  2 23  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  3 13  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 24  1  6  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  5 25  1  1  0  0  0
  6 11  1  0  0  0  0
  6 15  1  6  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 26  1  6  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 12 27  1  1  0  0  0
 13 19  1  0  0  0  0
 14 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 22  2  0  0  0  0
 18 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
FTBJKONNNSKOLX-XUDSTZEESA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.16254165540563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
4.313043906000002

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.278629439992315

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13401300388775417

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.7179

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norbolethone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0334747 (Norbolethone)
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PDB for NP0334747 (Norbolethone)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      37.854  -7.867   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.844 -13.939   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      35.149  -9.239   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.149 -10.779   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.816 -11.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.606  -8.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.482 -10.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.816  -8.469   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.606 -11.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.482  -9.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.505 -10.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.081 -11.559   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.149  -7.699   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.840 -13.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.133  -7.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.457 -13.965   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.068 -13.163   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.653 -10.691   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.816  -6.929   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.165  -6.162   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.194 -11.504   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.628 -14.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.181 -13.174   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      35.279 -12.389   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      33.860 -10.103   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      32.445 -12.216   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      31.104 -10.071   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   23                                                            
CONECT    3    4    6    8   13                                             
CONECT    4    3    5    9   24                                             
CONECT    5    4    7   14   25                                             
CONECT    6    1    3   11   15                                             
CONECT    7    5   10   12   26                                             
CONECT    8    3   10                                                       
CONECT    9    4   11                                                       
CONECT   10    7    8                                                       
CONECT   11    6    9                                                       
CONECT   12    7   17   18   27                                             
CONECT   13    3   19                                                       
CONECT   14    5   16                                                       
CONECT   15    6   20                                                       
CONECT   16   14   17                                                       
CONECT   17   12   16   22                                                  
CONECT   18   12   21                                                       
CONECT   19   13                                                            
CONECT   20   15                                                            
CONECT   21   18   23                                                       
CONECT   22   17   23                                                       
CONECT   23    2   21   22                                                  
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27   12                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

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3D PDB for NP0334747 (Norbolethone)
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SMILES for NP0334747 (Norbolethone)
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
Download
INCHI for NP0334747 (Norbolethone)
InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1
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Synonyms
ValueSource
NorboletoneHMDB
(+/-)-13,17a-diethyl-17b-hydroxygon-4-en-3-oneHMDB
(+/-)-13-ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-oneHMDB
(+/-)-13b,17a-diethyl-17b-hydroxygon-4-en-3-oneHMDB
(+/-)-17a-ethyl-18-homo-19-nortestosteroneHMDB
(17a)-(+/-)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-en-3-oneHMDB
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-oneHMDB
DL-13,17a-Diethyl-17-hydroxygon-4-en-3-oneHMDB
DL-13,17a-Diethyl-17b-hydroxygon-4-en-3-oneHMDB
DL-17b-Hydroxy-13b,17a-diethylgon-4-en-3-oneHMDB
DL-NorbolethoneHMDB
GenabolHMDB
Wy 3475HMDB
13-EHDPOHMDB
13-Ethyl-17-hydroxy-18,19-dinor-17-pregn-4-en-20-yn-3-oneHMDB
Chemical FormulaC21H32O2
Average Mass316.4776 Da
Monoisotopic Mass316.24023 Da
IUPAC Name(1S,2R,10R,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namenorbolethone
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI KeyFTBJKONNNSKOLX-XUDSTZEESA-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 gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassPregnane steroids  
Direct ParentGluco/mineralocorticoids, progestogins and derivatives  
Alternative Parents
Substituents
  • Progestogin-skeleton
    • 

  • 3-oxo-delta-4-steroid
    • 

  • 3-oxosteroid
    • 

  • 17-hydroxysteroid
    • 

  • Oxosteroid
    • 

  • Hydroxysteroid
    • 

  • Delta-4-steroid
    • 

  • Cyclohexenone
    • 

  • Cyclic alcohol
    • 

  • Tertiary alcohol
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic 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
logP4.02ALOGPS
logP4.31ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.28ChemAxon
pKa (Strongest Basic)-0.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.72 m³·mol⁻¹ChemAxon
Polarizability38.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006026  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023805  
KNApSAcK IDNot Available
Chemspider ID59638  
KEGG Compound IDD05204   
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorboletone  
METLIN IDNot Available
PubChem Compound66255  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Catlin DH, Ahrens BD, Kucherova Y: Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine. Rapid Commun Mass Spectrom. 2002;16(13):1273-5. doi: 10.1002/rcm.722. [PubMed:12112254  ]