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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 22:35:49 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004627

Secondary Accession Numbers

HMDB04627

Metabolite Identification

Common Name

Calusterone

Description

Calusterone is an androgenic steroid. Calusterone induce given orally induce a marked decrease (between 30 and 70% depending on the dose) in the binding capacity of oestradiol-17beta to specific uterine receptors in vivo. As an androgen, calusterone has been used as a therapeutic agent in postmenopausal women with metastatic breast cancer; the addition of a potent hormonal agent to effective cytotoxic chemotherapy improves the results of treatment of women with metastatic breast cancer. Calusterone is tested in sport screening; fast and sensitive method for the comprehensive screening of anabolic agents and other banned doping substances using gas chromatography/tandem mass spectrometry (GC/MS/MS) with an external ionization ion trap mass spectrometer have been developed for the parent substances and their metabolites. (PMID: 17610244 , 12375280 , 153787 , 2325376 , 12375280 ).

Structure

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

1564
  Mrv0541 02231215342D          

 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  2  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  1  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

HMDB0004627
     RDKit          3D
Calusterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    0.9358    0.5121    3.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5761    1.0659    1.6466 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7920    1.7619    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645    0.9950    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.1456    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    0.3044   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -0.0952   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0945    0.0058   -2.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    0.2531   -1.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0633   -0.0548   -0.6126 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6039   -1.3836   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -0.0096   -0.6383 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0310   -1.2175   -1.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -0.8948   -1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -0.6772   -0.3874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2616   -2.0341    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    0.3296    0.5361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3754    0.2827    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7533    0.2191    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946   -0.0867   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5829    1.2103   -1.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3921   -1.0405   -0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    0.0410    0.7754 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7522   -0.2126    2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    1.3985    3.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0448    0.1683    3.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.8743    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952    2.7582    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    2.0908    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454    1.8828    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713   -1.0074   -2.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    0.7271   -2.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    1.3526   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293   -0.2647   -2.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -1.2664    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131   -2.0028    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -1.9117   -0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204    0.8934   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5858   -1.4631   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250   -2.1052   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -0.0392   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -1.7767   -2.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3654   -2.3114    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1395   -2.0809    0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -2.7709   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576    1.3195    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1951   -0.6352    2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741    1.1951    2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3894   -0.5602    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3008    1.1795    1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800    2.0994   -0.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345    1.2101   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7582    1.4231   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3205   -0.8479   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963   -0.9490    1.2712 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  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 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  1
  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  6
 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  6
 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  1
M  END

1564
  Mrv0541 02231215342D          

 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  2  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  1  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>
HMDB0004627

> <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-/m0/s1

> <INCHI_KEY>
IVFYLRMMHVYGJH-PVPPCFLZSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.77128360682956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,9S,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>
calusterone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0004627
     RDKit          3D
Calusterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    0.9358    0.5121    3.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5761    1.0659    1.6466 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7920    1.7619    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645    0.9950    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.1456    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    0.3044   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -0.0952   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0945    0.0058   -2.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    0.2531   -1.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0633   -0.0548   -0.6126 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6039   -1.3836   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -0.0096   -0.6383 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0310   -1.2175   -1.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -0.8948   -1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -0.6772   -0.3874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2616   -2.0341    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    0.3296    0.5361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3754    0.2827    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7533    0.2191    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946   -0.0867   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5829    1.2103   -1.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3921   -1.0405   -0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    0.0410    0.7754 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7522   -0.2126    2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    1.3985    3.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0448    0.1683    3.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.8743    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952    2.7582    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    2.0908    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454    1.8828    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713   -1.0074   -2.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    0.7271   -2.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    1.3526   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293   -0.2647   -2.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -1.2664    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131   -2.0028    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -1.9117   -0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204    0.8934   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5858   -1.4631   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250   -2.1052   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -0.0392   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -1.7767   -2.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3654   -2.3114    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1395   -2.0809    0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -2.7709   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576    1.3195    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1951   -0.6352    2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741    1.1951    2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3894   -0.5602    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3008    1.1795    1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800    2.0994   -0.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345    1.2101   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7582    1.4231   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3205   -0.8479   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963   -0.9490    1.2712 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  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 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  1
  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  6
 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  6
 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  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1564                                              
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    HMDB0004627
HETATM    1  C1  UNL     1       0.936   0.512   3.037  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.576   1.066   1.647  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.792   1.762   1.158  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.664   0.995   0.271  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.973   1.146   0.171  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.745   0.304  -0.771  1.00  0.00           C  
HETATM    7  O1  UNL     1       5.859  -0.095  -0.437  1.00  0.00           O  
HETATM    8  C7  UNL     1       4.095   0.006  -2.075  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.604   0.253  -1.993  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.063  -0.055  -0.613  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.604  -1.384  -0.124  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.593  -0.010  -0.638  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.031  -1.218  -1.340  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.436  -0.895  -1.665  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.128  -0.677  -0.387  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.262  -2.034   0.314  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.462   0.330   0.536  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.375   0.283   1.696  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.753   0.219   1.036  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.495  -0.087  -0.446  1.00  0.00           C  
HETATM   21  C20 UNL     1      -3.583   1.210  -1.179  1.00  0.00           C  
HETATM   22  O2  UNL     1      -4.392  -1.040  -0.912  1.00  0.00           O  
HETATM   23  C21 UNL     1      -0.028   0.041   0.775  1.00  0.00           C  
HETATM   24  H1  UNL     1       1.752  -0.213   2.969  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.326   1.399   3.596  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.045   0.168   3.573  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.183   1.874   1.888  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.495   2.758   0.701  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.450   2.091   2.021  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.445   1.883   0.787  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.271  -1.007  -2.439  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.499   0.727  -2.814  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.402   1.353  -2.149  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.029  -0.265  -2.755  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.401  -1.266   0.638  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.813  -2.003   0.354  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.066  -1.912  -0.991  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.220   0.893  -1.152  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.586  -1.463  -2.228  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.025  -2.105  -0.656  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.414  -0.039  -2.356  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.834  -1.777  -2.165  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.365  -2.311   0.868  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.140  -2.081   0.964  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.449  -2.771  -0.515  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.558   1.320   0.040  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.195  -0.635   2.321  1.00  0.00           H  
HETATM   48  H25 UNL     1      -2.374   1.195   2.324  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.389  -0.560   1.501  1.00  0.00           H  
HETATM   50  H27 UNL     1      -4.301   1.179   1.148  1.00  0.00           H  
HETATM   51  H28 UNL     1      -3.680   2.099  -0.495  1.00  0.00           H  
HETATM   52  H29 UNL     1      -4.535   1.210  -1.767  1.00  0.00           H  
HETATM   53  H30 UNL     1      -2.758   1.423  -1.858  1.00  0.00           H  
HETATM   54  H31 UNL     1      -5.321  -0.848  -0.680  1.00  0.00           H  
HETATM   55  H32 UNL     1       0.096  -0.949   1.271  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

HMDB0004627
     RDKit          3D
Calusterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    0.9358    0.5121    3.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5761    1.0659    1.6466 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7920    1.7619    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645    0.9950    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.1456    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    0.3044   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -0.0952   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0945    0.0058   -2.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    0.2531   -1.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0633   -0.0548   -0.6126 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6039   -1.3836   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -0.0096   -0.6383 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0310   -1.2175   -1.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -0.8948   -1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -0.6772   -0.3874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2616   -2.0341    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    0.3296    0.5361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3754    0.2827    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7533    0.2191    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946   -0.0867   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5829    1.2103   -1.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3921   -1.0405   -0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    0.0410    0.7754 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7522   -0.2126    2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    1.3985    3.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0448    0.1683    3.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.8743    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952    2.7582    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    2.0908    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454    1.8828    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713   -1.0074   -2.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    0.7271   -2.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    1.3526   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293   -0.2647   -2.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -1.2664    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131   -2.0028    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -1.9117   -0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204    0.8934   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5858   -1.4631   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250   -2.1052   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -0.0392   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -1.7767   -2.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3654   -2.3114    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1395   -2.0809    0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -2.7709   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576    1.3195    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1951   -0.6352    2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741    1.1951    2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3894   -0.5602    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3008    1.1795    1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800    2.0994   -0.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345    1.2101   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7582    1.4231   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3205   -0.8479   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963   -0.9490    1.2712 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  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 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  1
  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  6
 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  6
 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  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(7b,17b)-17-Hydroxy-7,17-dimethyl-androst-4-en-3-one	HMDB
17-beta-Hydroxy-7-beta,17-alpha-dimethylandrost-4-ene-3-one	HMDB
17-beta-Hydroxy-7-beta-17-dimethyl androst-4-en-3-one	HMDB
17-Dimethyl-17beta-hydroxy-7beta-androst-4-en-3-one	HMDB
17-Hydroxy-7,17-dimethylandrost-4-en-3-one	HMDB
17b-Hydroxy-7b,17-dimethyl-androst-4-en-3-one	HMDB
17b-Hydroxy-7b,17-dimethylandrost-4-en-3-one	HMDB
17beta-Dimethyl testosterone	HMDB
17beta-Hydroxy-7beta-17-dimethylandrost-4-en-3-one	HMDB
17beta-Hydroxy-7beta-17alpha-dimethylandrost-4-ene-3-one	HMDB
7-beta,17-alpha-Dimethyl testosterone	HMDB
7-beta,17-Dimethyltestosterone	HMDB
7-beta-17-alpha-Dimethyltestosterone	HMDB
7beta,17alpha-Dimethyltestosterone	HMDB
7beta,17beta-Dimethyltestosterone	HMDB
7beta-Dimethyltestosterone	HMDB
Calusteron	HMDB
Calusterona	HMDB
Calusteronum	HMDB
Dimethyltestosterone	HMDB
Methosarb	HMDB
7 beta,17 alpha-Dimethyltestosterone	MeSH, HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

IUPAC Name

(1S,2R,9S,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

calusterone

CAS Registry Number

17021-26-0

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-/m0/s1

InChI Key

IVFYLRMMHVYGJH-PVPPCFLZSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004627)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0004627)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004627)

Source

Exogenous

Exogenous (HMDB: HMDB0004627)

Food

Food (HMDB: HMDB0004627)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004627)

Molecular messenger

Hormone (HMDB: HMDB0004627)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004627)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0004627)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128 °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	37.77 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]+	174.845	31661259
DarkChem	[M-H]-	172.17	31661259
DeepCCS	[M-2H]-	211.757	30932474
DeepCCS	[M+Na]+	186.418	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	187.6	32859911
AllCCS	[M+HCOO]-	188.1	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.	7.54 minutes	32390414
Predicted by Siyang on May 30, 2022	19.6047 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2865.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	570.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	237.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	857.0 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	881.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1573.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	521.2 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	1664.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	556.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	488.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	621.3 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calusterone	[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
Calusterone	[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
Calusterone	[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
Calusterone,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]12	2816.3	Semi standard non polar	33892256
Calusterone,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]12	2688.8	Semi standard non polar	33892256
Calusterone,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]12	2747.6	Semi standard non polar	33892256
Calusterone,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]12	2787.3	Standard non polar	33892256
Calusterone,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]12	2854.2	Standard polar	33892256
Calusterone,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]12	3052.8	Semi standard non polar	33892256
Calusterone,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]12	2958.6	Semi standard non polar	33892256
Calusterone,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]12	3263.7	Semi standard non polar	33892256
Calusterone,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]12	3250.2	Standard non polar	33892256
Calusterone,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]12	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 - Calusterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0292000000-d45cc06905f97c71acb7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calusterone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-1219000000-a3d8e93a3429c1b5b79e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calusterone 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 - Calusterone 10V, Positive-QTOF	splash10-00kb-0095000000-24b926788859812bd140	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 20V, Positive-QTOF	splash10-00kb-0291000000-d17e4bd109b597541b52	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 40V, Positive-QTOF	splash10-0zi9-3490000000-b1ee70c1893fd95ab783	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 10V, Negative-QTOF	splash10-014i-0029000000-6f88574915ba36904ede	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 20V, Negative-QTOF	splash10-014i-0059000000-88ccda88856d7b515ee6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 40V, Negative-QTOF	splash10-00kb-0090000000-6f3e258701147d991147	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 10V, Positive-QTOF	splash10-014i-0749000000-4e378b170e7e0e501a17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 20V, Positive-QTOF	splash10-002f-3911000000-3d55560ae9987134faeb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 40V, Positive-QTOF	splash10-000f-0900000000-1206f2feee3fa74b8674	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 10V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 20V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calusterone 40V, Negative-QTOF	splash10-014i-0097000000-3e67e2b99b64bbb19dde	2021-09-22	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

DB01564

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023386

KNApSAcK ID

Not Available

Chemspider ID

26239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calusterone

METLIN ID

Not Available

PubChem Compound

28204

PDB ID

Not Available

ChEBI ID

554295

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Campbell, J. Allan; Babcock, John C. The synthesis of some 7a- and 7b-methyl steroid hormones. Journal of the American Chemical Society (1959), 81 4069-74.

Material Safety Data Sheet (MSDS)

Not Available

General References

Georgakopoulos CG, Vonaparti A, Stamou M, Kiousi P, Lyris E, Angelis YS, Tsoupras G, Wuest B, Nielen MW, Panderi I, Koupparis M: Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun Mass Spectrom. 2007;21(15):2439-46. [PubMed:17610244 ]
Marcos J, Pascual JA, de la Torre X, Segura J: Fast screening of anabolic steroids and other banned doping substances in human urine by gas chromatography/tandem mass spectrometry. J Mass Spectrom. 2002 Oct;37(10):1059-73. [PubMed:12375280 ]
Lloyd RE, Jones SE, Salmon SE: Comparative trial of low-dose adriamycin plus cyclophosphamide with or without additive hormonal therapy in advanced breast cancer. Cancer. 1979 Jan;43(1):60-5. [PubMed:153787 ]
Choo HY, Kwon OS, Park J: Quantitative determination of stanozolol and its metabolite in urine by gas chromatography/mass spectrometry. J Anal Toxicol. 1990 Mar-Apr;14(2):109-12. [PubMed:2325376 ]

Showing metabocard for Calusterone (HMDB0004627)

MOL for HMDB0004627 (Calusterone)

3D MOL for HMDB0004627 (Calusterone)

3D SDF for HMDB0004627 (Calusterone)

3D-SDF for HMDB0004627 (Calusterone)

PDB for HMDB0004627 (Calusterone)

3D PDB for HMDB0004627 (Calusterone)

SMILES for HMDB0004627 (Calusterone)

INCHI for HMDB0004627 (Calusterone)

Structure for HMDB0004627 (Calusterone)

3D Structure for HMDB0004627 (Calusterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra