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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 21:14:39 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0006048

Secondary Accession Numbers

HMDB06048

Metabolite Identification

Common Name

Bolasterone

Description

Bolasterone is an anabolic androgenic steroid. Analysis of steroids in urine has been used to detect different hormonal actions in human beings such as testicular function in men, hyperandrogenic disorders in women and puberty problems in children, by the measurement of anabolic steroids, and some hormonal disorders such as adrenocortical adenoma and Cushing syndrome by the control of corticoids. This steroid have been included in the International Olympic Committee (IOC) doping list due to their illegal use in some sports and in the list of schedules drugs in several countries because of its use by young people. In addition, the examination of endogenous steroids profile provides information about the health and the use of exogenous steroids. Bolasterone is excreted as the original compound in human urine. 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. The use of anabolic steroids was banned by the International Olympic Committee for the first time at the Olympic Games in Montreal in 1976. Since that time the misuse of anabolic steroids by athletes has been controlled by analysis of urine of the excreted steroids or their metabolites, or both. (PMID: 10892583 , 10932808 , 14976846 , 15042372 , 15231229 , 3308301 , 8456050 , 8674183 , 16040239 ).

Structure

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

1471
  Mrv0541 02231215302D          

 26 29  0  0  1  0            999 V2000
    7.5474    1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0987    0.7597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3843   -0.4777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6698   -0.0653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8793    1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9192   -0.4833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843    1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698    0.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8793   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3975   -1.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3606    0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685   -0.7215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583   -0.8032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415    0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 23  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  3 24  1  6  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 16  1  1  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 25  1  1  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 26  1  6  0  0  0
  7 13  1  0  0  0  0
  7 18  1  0  0  0  0
  8 15  1  0  0  0  0
  8 17  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  6  0  0  0
 14 15  1  0  0  0  0
 15 22  2  0  0  0  0
 17 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END

HMDB0006048
     RDKit          3D
Bolasterone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.3326    3.1874   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566    1.8069   -0.3217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8649    1.7675    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618    0.6509    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    0.7053    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760   -0.4442    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1054   -0.3311    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2427   -1.7738    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -1.7173    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -0.5596   -0.0983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4078   -0.6199   -1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6752   -0.5377    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0400   -1.8212   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -1.7830   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.4659   -0.2433 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4099   -0.2711   -1.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382    0.6885    0.3296 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580    1.8072    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745    1.1648    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -0.2870    0.4381 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6697   -1.1337    1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -0.5972   -0.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    0.6741   -0.3517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0784    3.5674    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2070    3.8578   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4307    3.4178   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    1.7281   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    2.7140    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603    1.7157    1.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4562    1.5988    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -2.5462    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134   -2.1525   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063   -1.5388    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -2.6914    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -1.6667   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    0.0805   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041   -0.4657   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.3538    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742   -2.5980    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3677   -2.2123   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -2.2428    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -2.5041   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    0.7507   -2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6314   -0.7957   -2.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584   -0.8479   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2158    0.4077    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949    2.6294    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    2.2714   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996    1.2779    1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    1.6716    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5529   -0.7273    2.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212   -2.1917    1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8145   -1.0574    2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5735   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275    0.3672   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  6
 17 23  1  0
 23  2  1  0
 10  4  1  0
 23 12  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  5 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  6
M  END

1471
  Mrv0541 02231215302D          

 26 29  0  0  1  0            999 V2000
    7.5474    1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0987    0.7597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3843   -0.4777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6698   -0.0653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8793    1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9192   -0.4833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843    1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698    0.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8793   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3975   -1.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3606    0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685   -0.7215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583   -0.8032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415    0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 23  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  3 24  1  6  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 16  1  1  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 25  1  1  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 26  1  6  0  0  0
  7 13  1  0  0  0  0
  7 18  1  0  0  0  0
  8 15  1  0  0  0  0
  8 17  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  6  0  0  0
 14 15  1  0  0  0  0
 15 22  2  0  0  0  0
 17 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006048

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16+,17+,18-,19+,20+,21+/m1/s1

> <INCHI_KEY>
IVFYLRMMHVYGJH-VLOLGRDOSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.53930412277785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,9R,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.933019062333334

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.564040768992434

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5280731514980953

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.61659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bolasterone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006048
     RDKit          3D
Bolasterone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.3326    3.1874   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566    1.8069   -0.3217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8649    1.7675    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618    0.6509    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    0.7053    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760   -0.4442    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1054   -0.3311    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2427   -1.7738    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -1.7173    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -0.5596   -0.0983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4078   -0.6199   -1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6752   -0.5377    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0400   -1.8212   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -1.7830   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.4659   -0.2433 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4099   -0.2711   -1.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382    0.6885    0.3296 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580    1.8072    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745    1.1648    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -0.2870    0.4381 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6697   -1.1337    1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -0.5972   -0.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    0.6741   -0.3517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0784    3.5674    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2070    3.8578   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4307    3.4178   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    1.7281   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    2.7140    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603    1.7157    1.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4562    1.5988    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -2.5462    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134   -2.1525   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063   -1.5388    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -2.6914    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -1.6667   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    0.0805   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041   -0.4657   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.3538    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742   -2.5980    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3677   -2.2123   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -2.2428    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -2.5041   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    0.7507   -2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6314   -0.7957   -2.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584   -0.8479   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2158    0.4077    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949    2.6294    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    2.2714   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996    1.2779    1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    1.6716    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5529   -0.7273    2.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212   -2.1917    1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8145   -1.0574    2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5735   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275    0.3672   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  6
 17 23  1  0
 23  2  1  0
 10  4  1  0
 23 12  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  5 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  6
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1471                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      14.088   2.790   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.282   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.384  -0.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.384   1.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.051  -0.892   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.717  -0.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.841   1.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.316  -0.902   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.051   2.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.717   1.418   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.841  -0.591   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.075  -2.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.740   0.648   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.693  -3.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.304  -2.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.384   2.958   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -0.034   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.368   3.353   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.328   0.638   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.418  -3.250   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.429  -0.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.863  -3.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.416  -2.517   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      11.514  -1.347   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      11.122  -1.499   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       9.784   0.494   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   23                                                            
CONECT    3    4    5   11   24                                             
CONECT    4    3    7    9   16                                             
CONECT    5    3    6   12   25                                             
CONECT    6    5    8   10   26                                             
CONECT    7    1    4   13   18                                             
CONECT    8    6   15   17   19                                             
CONECT    9    4   10                                                       
CONECT   10    6    9                                                       
CONECT   11    3   13                                                       
CONECT   12    5   14   20                                                  
CONECT   13    7   11                                                       
CONECT   14   12   15                                                       
CONECT   15    8   14   22                                                  
CONECT   16    4                                                            
CONECT   17    8   21                                                       
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   12                                                            
CONECT   21   17   23                                                       
CONECT   22   15   23                                                       
CONECT   23    2   21   22                                                  
CONECT   24    3                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0006048
HETATM    1  C1  UNL     1      -0.333   3.187  -0.336  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.857   1.807  -0.322  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.865   1.767   0.843  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.762   0.651   0.545  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.044   0.705   0.823  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.876  -0.444   0.498  1.00  0.00           C  
HETATM    7  O1  UNL     1      -6.105  -0.331   0.386  1.00  0.00           O  
HETATM    8  C7  UNL     1      -4.243  -1.774   0.298  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.755  -1.717   0.646  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.125  -0.560  -0.098  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.408  -0.620  -1.567  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.675  -0.538   0.247  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.040  -1.821  -0.022  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.510  -1.783  -0.065  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.168  -0.466  -0.243  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.410  -0.271  -1.735  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.338   0.688   0.330  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.258   1.807   0.285  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.574   1.165   0.765  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.470  -0.287   0.438  1.00  0.00           C  
HETATM   21  C20 UNL     1       3.670  -1.134   1.661  1.00  0.00           C  
HETATM   22  O2  UNL     1       4.530  -0.597  -0.443  1.00  0.00           O  
HETATM   23  C21 UNL     1       0.057   0.674  -0.352  1.00  0.00           C  
HETATM   24  H1  UNL     1      -0.078   3.567   0.699  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.207   3.858  -0.614  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.431   3.418  -1.078  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.549   1.728  -1.219  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.422   2.714   0.789  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.360   1.716   1.813  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.456   1.599   1.286  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.679  -2.546   0.986  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.413  -2.152  -0.725  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.706  -1.539   1.733  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.310  -2.691   0.391  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.749  -1.667  -1.800  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.215   0.081  -1.869  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.504  -0.466  -2.190  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.619  -0.354   1.343  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.274  -2.598   0.718  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.368  -2.212  -1.003  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.944  -2.243   0.874  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.859  -2.504  -0.866  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.597   0.751  -2.022  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.631  -0.796  -2.345  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.358  -0.848  -1.951  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.216   0.408   1.421  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.095   2.629   1.033  1.00  0.00           H  
HETATM   48  H25 UNL     1       2.493   2.271  -0.668  1.00  0.00           H  
HETATM   49  H26 UNL     1       3.700   1.278   1.855  1.00  0.00           H  
HETATM   50  H27 UNL     1       4.447   1.672   0.294  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.553  -0.727   2.202  1.00  0.00           H  
HETATM   52  H29 UNL     1       3.921  -2.192   1.429  1.00  0.00           H  
HETATM   53  H30 UNL     1       2.815  -1.057   2.372  1.00  0.00           H  
HETATM   54  H31 UNL     1       4.647  -1.573  -0.533  1.00  0.00           H  
HETATM   55  H32 UNL     1       0.227   0.367  -1.429  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23   27
CONECT    3    4   28   29
CONECT    4    5    5   10
CONECT    5    6   30
CONECT    6    7    7    8
CONECT    8    9   31   32
CONECT    9   10   33   34
CONECT   10   11   12
CONECT   11   35   36   37
CONECT   12   13   23   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   17   20
CONECT   16   43   44   45
CONECT   17   18   23   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   22
CONECT   21   51   52   53
CONECT   22   54
CONECT   23   55
END

HMDB0006048
     RDKit          3D
Bolasterone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.3326    3.1874   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566    1.8069   -0.3217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8649    1.7675    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618    0.6509    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    0.7053    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760   -0.4442    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1054   -0.3311    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2427   -1.7738    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -1.7173    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -0.5596   -0.0983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4078   -0.6199   -1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6752   -0.5377    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0400   -1.8212   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -1.7830   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.4659   -0.2433 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4099   -0.2711   -1.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382    0.6885    0.3296 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580    1.8072    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745    1.1648    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -0.2870    0.4381 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6697   -1.1337    1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -0.5972   -0.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    0.6741   -0.3517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0784    3.5674    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2070    3.8578   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4307    3.4178   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    1.7281   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    2.7140    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603    1.7157    1.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4562    1.5988    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -2.5462    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134   -2.1525   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063   -1.5388    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -2.6914    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -1.6667   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    0.0805   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041   -0.4657   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.3538    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742   -2.5980    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3677   -2.2123   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -2.2428    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -2.5041   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    0.7507   -2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6314   -0.7957   -2.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584   -0.8479   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2158    0.4077    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949    2.6294    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    2.2714   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996    1.2779    1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    1.6716    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5529   -0.7273    2.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212   -2.1917    1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8145   -1.0574    2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5735   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275    0.3672   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  6
 17 23  1  0
 23  2  1  0
 10  4  1  0
 23 12  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  5 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7alpha,17alpha-Dimethyltestosterone	Kegg
17beta-Hydroxy-7alpha,17-dimethylandrost-4-en-3-one	Kegg
U19763	Kegg
7a,17a-Dimethyltestosterone	Generator
7Α,17α-dimethyltestosterone	Generator
17b-Hydroxy-7a,17-dimethylandrost-4-en-3-one	Generator
17Β-hydroxy-7α,17-dimethylandrost-4-en-3-one	Generator
(7a,17b)-17-Hydroxy-7,17-dimethyl-androst-4-en-3-one	HMDB
17b-Hydroxy-7a,17-dimethyl-androst-4-en-3-one	HMDB
17b-Hydroxy-7a,17a-dimethylandrost-4-ene-3-one	HMDB
7a,17-Dimethyl-testosterone	HMDB
7a,17a-Dimethyl-17b-hydroxyandrost-4-en-3-one	HMDB
Myagen	HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

IUPAC Name

(1S,2R,9R,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

bolasterone

CAS Registry Number

1605-89-6

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16+,17+,18-,19+,20+,21+/m1/s1

InChI Key

IVFYLRMMHVYGJH-VLOLGRDOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Ketone
Cyclic ketone
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:34583 )
C19 steroids (androgens) and derivatives (LMST02020017 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0006048)
Cell membrane (HMDB: HMDB0006048)

Biofluid or Excreta

Urine (HMDB: HMDB0006048)

Tissue substructure

Hepatic tissue (HMDB: HMDB0006048)

Cellular substructure

Extracellular (HMDB: HMDB0006048)
Membrane (HMDB: HMDB0006048)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006048)

Source

Endogenous

Endogenous (HMDB: HMDB0006048)

Exogenous

Food

Food (HMDB: HMDB0006048)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0006048)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0006048)

Cellular process

Cell signaling (HMDB: HMDB0006048)

System process

Reproduction (HMDB: HMDB0006048)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0006048)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006048)

Molecular messenger

Hormone (HMDB: HMDB0006048)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006048)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006048)

Emulsifier (HMDB: HMDB0006048)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	164 °C	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	0.011 g/L	ALOGPS
logP	3.55	ALOGPS
logP	3.93	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	19.56	ChemAxon
pKa (Strongest Basic)	-0.53	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	0	ChemAxon
Refractivity	93.62 m³·mol⁻¹	ChemAxon
Polarizability	37.54 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]+	175.16	31661259
DarkChem	[M-H]-	172.526	31661259
DeepCCS	[M-2H]-	211.912	30932474
DeepCCS	[M+Na]+	186.424	30932474
AllCCS	[M+H]+	180.2	32859911
AllCCS	[M+H-H2O]+	177.3	32859911
AllCCS	[M+NH4]+	182.9	32859911
AllCCS	[M+Na]+	183.7	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	187.6	32859911
AllCCS	[M+HCOO]-	188.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bolasterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C	3592.7	Standard polar	33892256
Bolasterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C	2653.3	Standard non polar	33892256
Bolasterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C	2808.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bolasterone,1TMS,isomer #1	C[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]21	2816.3	Semi standard non polar	33892256
Bolasterone,1TMS,isomer #2	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O)[C@@H]21	2688.8	Semi standard non polar	33892256
Bolasterone,2TMS,isomer #1	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]21	2747.6	Semi standard non polar	33892256
Bolasterone,2TMS,isomer #1	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]21	2787.3	Standard non polar	33892256
Bolasterone,2TMS,isomer #1	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]21	2854.2	Standard polar	33892256
Bolasterone,1TBDMS,isomer #1	C[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C(C)(C)C)[C@@H]21	3052.8	Semi standard non polar	33892256
Bolasterone,1TBDMS,isomer #2	C[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O)[C@@H]21	2958.6	Semi standard non polar	33892256
Bolasterone,2TBDMS,isomer #1	C[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C(C)(C)C)[C@@H]21	3263.7	Semi standard non polar	33892256
Bolasterone,2TBDMS,isomer #1	C[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C(C)(C)C)[C@@H]21	3250.2	Standard non polar	33892256
Bolasterone,2TBDMS,isomer #1	C[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C(C)(C)C)[C@@H]21	3074.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bolasterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0292000000-d45cc06905f97c71acb7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolasterone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-1219000000-a3d8e93a3429c1b5b79e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolasterone 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 - Bolasterone 10V, Negative-QTOF	splash10-014i-0029000000-6f88574915ba36904ede	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 20V, Negative-QTOF	splash10-014i-0059000000-88ccda88856d7b515ee6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 40V, Negative-QTOF	splash10-00kb-0090000000-6f3e258701147d991147	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 10V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 20V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 40V, Negative-QTOF	splash10-014i-0097000000-3e67e2b99b64bbb19dde	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 10V, Positive-QTOF	splash10-00kb-0095000000-24b926788859812bd140	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 20V, Positive-QTOF	splash10-00kb-0291000000-d17e4bd109b597541b52	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 40V, Positive-QTOF	splash10-0zi9-3490000000-b1ee70c1893fd95ab783	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 10V, Positive-QTOF	splash10-014i-0749000000-4e378b170e7e0e501a17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 20V, Positive-QTOF	splash10-002f-3911000000-3d55560ae9987134faeb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolasterone 40V, Positive-QTOF	splash10-000f-0900000000-1206f2feee3fa74b8674	2021-09-24	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

DB01471

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023820

KNApSAcK ID

Not Available

Chemspider ID

92280

KEGG Compound ID

C14475

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bolasterone

METLIN ID

Not Available

PubChem Compound

102146

PDB ID

Not Available

ChEBI ID

529021

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

Hungerford NL, Sortais B, Smart CG, McKinney AR, Ridley DD, Stenhouse AM, Suann CJ, Munn KJ, Sillence MN, McLeod MD: Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites. J Steroid Biochem Mol Biol. 2005 Aug;96(3-4):317-34. [PubMed:16040239 ]
Yesalis CE, Bahrke MS: Doping among adolescent athletes. Baillieres Best Pract Res Clin Endocrinol Metab. 2000 Mar;14(1):25-35. [PubMed:10932808 ]
Furlanello F, Bentivegna S, Cappato R, De Ambroggi L: Arrhythmogenic effects of illicit drugs in athletes. Ital Heart J. 2003 Dec;4(12):829-37. [PubMed:14976846 ]
Bricout V, Wright F: Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances? Eur J Appl Physiol. 2004 Jun;92(1-2):1-12. Epub 2004 Mar 20. [PubMed:15042372 ]
Foster ZJ, Housner JA: Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport. Curr Sports Med Rep. 2004 Aug;3(4):234-41. [PubMed:15231229 ]
Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68. [PubMed:3308301 ]
Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103. [PubMed:8456050 ]
Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20. [PubMed:8674183 ]
Gonzalo-Lumbreras R, Izquierdo-Hornillos R: Optimization of the high-performance liquid chromatographic separation of a complex mixture containing urinary steroids, boldenone and bolasterone: application to urine samples. J Chromatogr B Biomed Sci Appl. 2000 May 26;742(1):47-57. [PubMed:10892583 ]

Showing metabocard for Bolasterone (HMDB0006048)

MOL for HMDB0006048 (Bolasterone)

3D MOL for HMDB0006048 (Bolasterone)

3D SDF for HMDB0006048 (Bolasterone)

3D-SDF for HMDB0006048 (Bolasterone)

PDB for HMDB0006048 (Bolasterone)

3D PDB for HMDB0006048 (Bolasterone)

SMILES for HMDB0006048 (Bolasterone)

INCHI for HMDB0006048 (Bolasterone)

Structure for HMDB0006048 (Bolasterone)

3D Structure for HMDB0006048 (Bolasterone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra