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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 20:33:51 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0006026

Secondary Accession Numbers

HMDB06026

Metabolite Identification

Common Name

Norbolethone

Description

Norbolethone is a 19-nor anabolic steroid first synthesized in 1966. During the 1960s it was administered to humans in efficacy studies concerned with short stature and underweight conditions. It has never been reported by doping control laboratories prior to 2001. Norbolethone was identified in two urine samples from one athlete by matching the mass spectra and chromatographic retention times with those of a reference standard. The samples also contained at least one likely metabolite. The samples were also unusual because the concentrations of endogenous steroids were exceptionally low. Since norbolethone is not known to be marketed by any pharmaceutical company, a clandestine source of norbolethone may exist. Norbolethone matches the description for what is described as a "designer steroid." Androgenic anabolic steroids (AAS) are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. (PMID: 12112254 ).

Structure

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


  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

HMDB0006026
     RDKit          3D
Norbolethone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.1897    1.2305    2.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789    1.1008    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    0.1184    0.6402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0669    0.2491   -0.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332   -1.3290    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7120   -1.9809    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8493   -0.8179    0.6291 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4673   -0.9559    0.0027 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3161   -2.0254    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -2.1963   -0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -0.8773   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -0.8840   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    0.3985   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0048    0.5016   -1.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    1.5460   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304    1.3379    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413    0.4191   -0.2799 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1713    0.3612    0.3428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3888    1.5779    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409    1.4931   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    0.1556   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9731   -0.4295   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762    0.2798   -2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069    0.2862    3.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    1.9384    3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    1.6971    2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551    0.7952    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057    2.0922    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183   -0.3491    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961   -1.8784    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1135   -1.3108    2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -2.7244   -0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -2.5995    1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478   -0.4259    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -1.1030   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -1.6905    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7553   -2.9699    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1728   -2.5311   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -2.9489    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -1.8295   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633    1.6460    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    2.5112   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324    0.8309    1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124    2.3184    0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540    0.8867   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650    0.2623    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    2.1632   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5171    2.2725    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    1.8183   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369    2.2521    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411   -0.4962   -2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -1.4915   -1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    1.3048   -2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606    0.2953   -3.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199   -0.2956   -2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END


  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>
HMDB0006026

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0006026
     RDKit          3D
Norbolethone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.1897    1.2305    2.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789    1.1008    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    0.1184    0.6402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0669    0.2491   -0.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332   -1.3290    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7120   -1.9809    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8493   -0.8179    0.6291 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4673   -0.9559    0.0027 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3161   -2.0254    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -2.1963   -0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -0.8773   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -0.8840   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    0.3985   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0048    0.5016   -1.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    1.5460   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304    1.3379    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413    0.4191   -0.2799 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1713    0.3612    0.3428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3888    1.5779    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409    1.4931   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    0.1556   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9731   -0.4295   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762    0.2798   -2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069    0.2862    3.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    1.9384    3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    1.6971    2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551    0.7952    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057    2.0922    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183   -0.3491    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961   -1.8784    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1135   -1.3108    2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -2.7244   -0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -2.5995    1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478   -0.4259    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -1.1030   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -1.6905    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7553   -2.9699    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1728   -2.5311   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -2.9489    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -1.8295   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633    1.6460    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    2.5112   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324    0.8309    1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124    2.3184    0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540    0.8867   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650    0.2623    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    2.1632   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5171    2.2725    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    1.8183   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369    2.2521    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411   -0.4962   -2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -1.4915   -1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    1.3048   -2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606    0.2953   -3.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199   -0.2956   -2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

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

COMPND    HMDB0006026
HETATM    1  C1  UNL     1      -2.190   1.230   2.807  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.179   1.101   1.724  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.961   0.118   0.640  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.067   0.249  -0.197  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.033  -1.329   1.149  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.712  -1.981   0.807  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.849  -0.818   0.629  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.467  -0.956   0.003  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.316  -2.025   0.670  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.545  -2.196  -0.197  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.197  -0.877  -0.412  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.476  -0.884  -0.754  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.131   0.399  -0.969  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.005   0.502  -1.869  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.743   1.546  -0.115  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.430   1.338   0.563  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.541   0.419  -0.280  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.171   0.361   0.343  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.389   1.578   0.076  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.041   1.493  -0.237  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.715   0.156  -0.138  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.973  -0.430  -1.510  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.976   0.280  -2.346  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.107   0.286   3.424  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.663   1.938   3.562  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.234   1.697   2.587  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.155   0.795   2.217  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.406   2.092   1.295  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.818  -0.349   0.104  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.896  -1.878   0.789  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.114  -1.311   2.272  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.769  -2.724  -0.005  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.358  -2.599   1.699  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.648  -0.426   1.679  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.559  -1.103  -1.060  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.631  -1.691   1.670  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.755  -2.970   0.662  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.173  -2.531  -1.207  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.244  -2.949   0.215  1.00  0.00           H  
HETATM   40  H17 UNL     1       5.014  -1.830  -0.870  1.00  0.00           H  
HETATM   41  H18 UNL     1       5.563   1.646   0.655  1.00  0.00           H  
HETATM   42  H19 UNL     1       4.780   2.511  -0.679  1.00  0.00           H  
HETATM   43  H20 UNL     1       3.532   0.831   1.548  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.912   2.318   0.661  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.454   0.887  -1.283  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.365   0.262   1.455  1.00  0.00           H  
HETATM   47  H24 UNL     1       0.944   2.163  -0.725  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.517   2.273   0.966  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.183   1.818  -1.315  1.00  0.00           H  
HETATM   50  H27 UNL     1      -1.637   2.252   0.311  1.00  0.00           H  
HETATM   51  H28 UNL     1      -1.041  -0.496  -2.115  1.00  0.00           H  
HETATM   52  H29 UNL     1      -2.313  -1.491  -1.448  1.00  0.00           H  
HETATM   53  H30 UNL     1      -3.239   1.305  -2.026  1.00  0.00           H  
HETATM   54  H31 UNL     1      -2.661   0.295  -3.447  1.00  0.00           H  
HETATM   55  H32 UNL     1      -3.920  -0.296  -2.391  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    5   21
CONECT    4   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   21   34
CONECT    8    9   18   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   12   17
CONECT   12   13   40
CONECT   13   14   14   15
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   45
CONECT   18   19   46
CONECT   19   20   47   48
CONECT   20   21   49   50
CONECT   21   22
CONECT   22   23   51   52
CONECT   23   53   54   55
END

HMDB0006026
     RDKit          3D
Norbolethone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.1897    1.2305    2.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789    1.1008    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    0.1184    0.6402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0669    0.2491   -0.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332   -1.3290    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7120   -1.9809    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8493   -0.8179    0.6291 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4673   -0.9559    0.0027 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3161   -2.0254    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -2.1963   -0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -0.8773   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -0.8840   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    0.3985   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0048    0.5016   -1.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    1.5460   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304    1.3379    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413    0.4191   -0.2799 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1713    0.3612    0.3428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3888    1.5779    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409    1.4931   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    0.1556   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9731   -0.4295   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762    0.2798   -2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069    0.2862    3.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    1.9384    3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    1.6971    2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551    0.7952    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057    2.0922    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183   -0.3491    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961   -1.8784    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1135   -1.3108    2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -2.7244   -0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -2.5995    1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478   -0.4259    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -1.1030   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -1.6905    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7553   -2.9699    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1728   -2.5311   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -2.9489    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -1.8295   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633    1.6460    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    2.5112   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324    0.8309    1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124    2.3184    0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540    0.8867   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650    0.2623    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    2.1632   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5171    2.2725    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    1.8183   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369    2.2521    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411   -0.4962   -2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -1.4915   -1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394    1.3048   -2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606    0.2953   -3.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199   -0.2956   -2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-EHDPO	MeSH
13-Ethyl-17-hydroxy-18,19-dinor-17-pregn-4-en-20-yn-3-one	MeSH
Norboletone	ChEMBL, HMDB
(+/-)-13,17a-diethyl-17b-hydroxygon-4-en-3-one	HMDB
(+/-)-13-ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-one	HMDB
(+/-)-13b,17a-diethyl-17b-hydroxygon-4-en-3-one	HMDB
(+/-)-17a-ethyl-18-homo-19-nortestosterone	HMDB
(17a)-(+/-)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-en-3-one	HMDB
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-one	HMDB
DL-13,17a-Diethyl-17-hydroxygon-4-en-3-one	HMDB
DL-13,17a-Diethyl-17b-hydroxygon-4-en-3-one	HMDB
DL-17b-Hydroxy-13b,17a-diethylgon-4-en-3-one	HMDB
DL-Norbolethone	HMDB
Genabol	HMDB
Wy 3475	HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

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 Name

norbolethone

CAS Registry Number

1235-15-0

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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006026)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006026)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006026)

Source

Exogenous

Exogenous (HMDB: HMDB0006026)

Food

Food (HMDB: HMDB0006026)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006026)

Molecular messenger

Hormone (HMDB: HMDB0006026)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006026)

Physical Properties

State

Solid

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
Water Solubility	0.0098 g/L	ALOGPS
logP	4.02	ALOGPS
logP	4.31	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19.28	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.72 m³·mol⁻¹	ChemAxon
Polarizability	38.16 Å³	ChemAxon
Number of Rings	4	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]+	174.955	31661259
DarkChem	[M-H]-	172.148	31661259
DeepCCS	[M-2H]-	211.842	30932474
DeepCCS	[M+Na]+	186.249	30932474
AllCCS	[M+H]+	182.1	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.7	32859911
AllCCS	[M+Na]+	185.5	32859911
AllCCS	[M-H]-	186.5	32859911
AllCCS	[M+Na-2H]-	186.9	32859911
AllCCS	[M+HCOO]-	187.4	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.7 minutes	32390414
Predicted by Siyang on May 30, 2022	18.6285 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.46 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2823.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	494.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	234.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	513.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	881.2 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	756.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1561.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.6 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	1652.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	533.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	311.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	531.1 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norbolethone	[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3745.9	Standard polar	33892256
Norbolethone	[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2738.0	Standard non polar	33892256
Norbolethone	[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2876.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norbolethone,1TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC	2929.8	Semi standard non polar	33892256
Norbolethone,1TMS,isomer #2	CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	2803.4	Semi standard non polar	33892256
Norbolethone,2TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	2855.5	Semi standard non polar	33892256
Norbolethone,2TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	2901.9	Standard non polar	33892256
Norbolethone,2TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3179.9	Standard polar	33892256
Norbolethone,1TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC	3175.7	Semi standard non polar	33892256
Norbolethone,1TBDMS,isomer #2	CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3068.3	Semi standard non polar	33892256
Norbolethone,2TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3381.8	Semi standard non polar	33892256
Norbolethone,2TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3367.2	Standard non polar	33892256
Norbolethone,2TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3365.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norbolethone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1291000000-d413aaf2b4edf2000360	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbolethone GC-MS (1 TMS) - 70eV, Positive	splash10-0c00-1119000000-352ad6792758ae9d94d7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbolethone 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 - Norbolethone 10V, Positive-QTOF	splash10-00kb-0095000000-cda25eaf9c10361b9222	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 20V, Positive-QTOF	splash10-0002-0191000000-7aa90a3e0c0842920d99	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 40V, Positive-QTOF	splash10-05di-1690000000-4a138059002b023720e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 10V, Negative-QTOF	splash10-014i-0029000000-98b78b3afa508c81ab7b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 20V, Negative-QTOF	splash10-014i-0069000000-9be5f2e135e6a2d1b47d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 40V, Negative-QTOF	splash10-052s-0090000000-810ee3872d7cdf37d1e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 10V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 20V, Negative-QTOF	splash10-014i-0019000000-eb65f94e6914722e1b9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 40V, Negative-QTOF	splash10-014i-0092000000-3816ecdb5ba24754d396	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 10V, Positive-QTOF	splash10-00kb-0096000000-12094c8bb5dfd35602b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 20V, Positive-QTOF	splash10-01ba-0791000000-6a375c28af2bcbf46d2b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbolethone 40V, Positive-QTOF	splash10-0691-1900000000-118c6246477fc37b89c4	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB023805

KNApSAcK ID

Not Available

Chemspider ID

59638

KEGG Compound ID

D05204

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norboletone

METLIN ID

Not Available

PubChem Compound

66255

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

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. [PubMed:12112254 ]

Showing metabocard for Norbolethone (HMDB0006026)

MOL for HMDB0006026 (Norbolethone)

3D MOL for HMDB0006026 (Norbolethone)

3D SDF for HMDB0006026 (Norbolethone)

3D-SDF for HMDB0006026 (Norbolethone)

PDB for HMDB0006026 (Norbolethone)

3D PDB for HMDB0006026 (Norbolethone)

SMILES for HMDB0006026 (Norbolethone)

INCHI for HMDB0006026 (Norbolethone)

Structure for HMDB0006026 (Norbolethone)

3D Structure for HMDB0006026 (Norbolethone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra