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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 22:41:35 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004631

Secondary Accession Numbers

HMDB04631

Metabolite Identification

Common Name

Formebolone

Description

Formebolone is a synthetic anabolic steroid. It is suspected of misuse in sports and therefore tested for in regular screening of athletes. The desire to artificially enhance physical performance in order to increase the chances to win in sports competition is supposedly as old as mankind itself. Already during the ancient Olympic Games, in approximately 200 B.C., athletes used concoctions of mushrooms and plant seeds, as well as special diets including bovine and canine testicles, as reported by Philostratos and Galen. The attempt to improve the power and strength of racing animals also has a long history, as it has been reported that the ancient Romans fed their horses so-called 'Hydromel', a mixture of honey and water, in order to increase endurance. The manipulation of the capacities of an athlete or animal has been referred to as doping since 1889, when this term, originating from a dialect spoken in the south-eastern region of Africa, was included in a British dictionary. With the athlete Linton, the first authentic doping-related death occurred in 1886 during a cycle race (Paris-Bordeaux), caused by an overdose of caffeine. (For a more complete review on doping see PMID: 15808003 ).

Structure

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

1569
  Mrv0541 02231215342D          

 28 31  0  0  1  0            999 V2000
    7.9810    1.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    1.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054    0.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5320   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8175   -0.4778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1031   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3127    1.0112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8175    1.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3127   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1031    0.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3523   -0.4834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7942    0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8308   -1.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -1.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0591    1.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5739   -1.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987   -1.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6019   -0.7216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -0.8033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6746    0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
 12  2  1  6  0  0  0
  3 24  2  0  0  0  0
  4 25  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 26  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 27  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 28  1  6  0  0  0
  9 14  1  0  0  0  0
  9 19  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 18  1  0  0  0  0
 13 20  1  1  0  0  0
 13 21  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

HMDB0004631
     RDKit          3D
Formebolone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.8639   -0.3534   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5079   -0.1712   -0.3807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3260   -1.0196    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.2400    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    1.6449    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    0.9095   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1220    0.7303    0.6295 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4597    2.0631    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    2.1016    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023    1.1075    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755    1.4770   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664    0.5657   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7752    0.9056   -1.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -0.7692   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8642   -1.7319   -1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3679   -2.8559   -2.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9214   -1.0997   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.2090    0.2183 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9375   -0.8514    1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    0.0177   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1225   -1.2473   -0.8983 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7252   -1.5477   -2.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -1.2095   -1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -0.4936   -0.0649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9690   -1.2419    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    0.2538   -2.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144    0.0330   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -1.4221   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.6475    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    1.9217   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    1.3127    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517    2.7464    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    1.2906    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660    1.2561   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    0.1234    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809    2.8102    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849    2.5193    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    1.8438    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    3.1185    1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2105    2.4928    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   -1.4337   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -2.1022   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -1.7030    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -1.2532    1.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -0.1185    2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639    0.7107   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.1122   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -2.1315   -2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -2.2534   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -0.7315   -2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.9122    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079   -1.9314    1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.6420    2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  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  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 14 17  2  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24  2  1  0
 24  6  1  0
 20  7  1  0
 18 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 15 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  6
 21 47  1  1
 22 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

1569
  Mrv0541 02231215342D          

 28 31  0  0  1  0            999 V2000
    7.9810    1.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    1.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054    0.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5320   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8175   -0.4778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1031   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3127    1.0112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8175    1.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3127   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1031    0.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3523   -0.4834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7942    0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8308   -1.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -1.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0591    1.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5739   -1.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987   -1.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6019   -0.7216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -0.8033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6746    0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
 12  2  1  6  0  0  0
  3 24  2  0  0  0  0
  4 25  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 26  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 27  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 28  1  6  0  0  0
  9 14  1  0  0  0  0
  9 19  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 18  1  0  0  0  0
 13 20  1  1  0  0  0
 13 21  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004631

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O4/c1-19-9-12(11-22)16(23)8-13(19)4-5-14-15-6-7-21(3,25)20(15,2)10-17(24)18(14)19/h8-9,11,14-15,17-18,24-25H,4-7,10H2,1-3H3/t14-,15-,17+,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
AMVODTGMYSRMNP-GNIMZFFESA-N

> <FORMULA>
C21H28O4

> <MOLECULAR_WEIGHT>
344.4446

> <EXACT_MASS>
344.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.125801070027165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-4-carbaldehyde

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
1.7636854946666674

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.0575368398266

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.392580264837278

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8510091417772525

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
96.90269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
formebolone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004631
     RDKit          3D
Formebolone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.8639   -0.3534   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5079   -0.1712   -0.3807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3260   -1.0196    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.2400    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    1.6449    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    0.9095   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1220    0.7303    0.6295 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4597    2.0631    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    2.1016    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023    1.1075    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755    1.4770   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664    0.5657   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7752    0.9056   -1.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -0.7692   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8642   -1.7319   -1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3679   -2.8559   -2.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9214   -1.0997   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.2090    0.2183 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9375   -0.8514    1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    0.0177   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1225   -1.2473   -0.8983 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7252   -1.5477   -2.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -1.2095   -1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -0.4936   -0.0649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9690   -1.2419    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    0.2538   -2.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144    0.0330   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -1.4221   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.6475    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    1.9217   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    1.3127    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517    2.7464    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    1.2906    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660    1.2561   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    0.1234    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809    2.8102    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849    2.5193    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    1.8438    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    3.1185    1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2105    2.4928    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   -1.4337   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -2.1022   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -1.7030    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -1.2532    1.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -0.1185    2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639    0.7107   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.1122   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -2.1315   -2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -2.2534   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -0.7315   -2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.9122    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079   -1.9314    1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.6420    2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  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  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 14 17  2  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24  2  1  0
 24  6  1  0
 20  7  1  0
 18 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 15 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  6
 21 47  1  1
 22 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1569                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      14.898   2.790   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.192   2.188   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.888  -3.282   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.930   1.479   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.193   1.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.193  -0.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.859  -0.892   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.526  -0.122   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.650   1.888   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.859   2.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.650  -0.591   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.526   1.418   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.124  -0.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.549   0.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.884  -2.496   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.193   2.958   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.501  -3.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.112  -2.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.177   3.353   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.136   0.638   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.697  -0.034   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.671  -3.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.237  -0.847   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.224  -2.518   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.913  -0.061   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      12.324  -1.347   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      11.931  -1.499   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      10.593   0.494   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   12                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6    9   10   16                                             
CONECT    6    5    7   11   26                                             
CONECT    7    6    8   15   27                                             
CONECT    8    7   12   13   28                                             
CONECT    9    1    5   14   19                                             
CONECT   10    5   12                                                       
CONECT   11    6   14                                                       
CONECT   12    2    8   10                                                  
CONECT   13    8   18   20   21                                             
CONECT   14    9   11                                                       
CONECT   15    7   17                                                       
CONECT   16    5                                                            
CONECT   17   15   18                                                       
CONECT   18   13   17   22                                                  
CONECT   19    9                                                            
CONECT   20   13                                                            
CONECT   21   13   23                                                       
CONECT   22   18   24                                                       
CONECT   23   21   24   25                                                  
CONECT   24    3   22   23                                                  
CONECT   25    4   23                                                       
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0004631
HETATM    1  C1  UNL     1      -3.864  -0.353  -1.832  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.508  -0.171  -0.381  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.326  -1.020   0.365  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.775   1.240   0.100  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.474   1.645   0.793  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.475   0.910  -0.003  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.122   0.730   0.630  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.460   2.063   0.932  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.908   2.102   1.249  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.702   1.107   0.422  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.875   1.477  -0.054  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.666   0.566  -0.846  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.775   0.906  -1.299  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.094  -0.769  -1.083  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.864  -1.732  -1.886  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.368  -2.856  -2.078  1.00  0.00           O  
HETATM   17  C14 UNL     1       2.921  -1.100  -0.591  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.084  -0.209   0.218  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.937  -0.851   1.590  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.721   0.018  -0.413  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.122  -1.247  -0.898  1.00  0.00           C  
HETATM   22  O4  UNL     1       0.725  -1.548  -2.145  1.00  0.00           O  
HETATM   23  C19 UNL     1      -1.349  -1.209  -1.138  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.085  -0.494  -0.065  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.969  -1.242   1.218  1.00  0.00           C  
HETATM   26  H1  UNL     1      -3.251   0.254  -2.517  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.914   0.033  -1.947  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.896  -1.422  -2.064  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.539  -0.647   1.254  1.00  0.00           H  
HETATM   30  H5  UNL     1      -3.914   1.922  -0.787  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.641   1.313   0.764  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.352   2.746   0.794  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.540   1.291   1.817  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.366   1.256  -1.028  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.178   0.123   1.536  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.281   2.810   0.107  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.085   2.519   1.811  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.103   1.844   2.305  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.359   3.118   1.106  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.211   2.493   0.180  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.824  -1.434  -2.277  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.555  -2.102  -0.803  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.255  -1.703   1.594  1.00  0.00           H  
HETATM   44  H19 UNL     1       2.937  -1.253   1.905  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.657  -0.119   2.365  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.864   0.711  -1.250  1.00  0.00           H  
HETATM   47  H22 UNL     1       0.428  -2.112  -0.239  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.106  -2.132  -2.662  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.720  -2.253  -1.211  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.503  -0.731  -2.149  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.876  -1.912   1.285  1.00  0.00           H  
HETATM   52  H27 UNL     1      -1.108  -1.931   1.261  1.00  0.00           H  
HETATM   53  H28 UNL     1      -1.971  -0.642   2.126  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   24
CONECT    3   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   24   34
CONECT    7    8   20   35
CONECT    8    9   36   37
CONECT    9   10   38   39
CONECT   10   11   11   18
CONECT   11   12   40
CONECT   12   13   13   14
CONECT   14   15   17   17
CONECT   15   16   16   41
CONECT   17   18   42
CONECT   18   19   20
CONECT   19   43   44   45
CONECT   20   21   46
CONECT   21   22   23   47
CONECT   22   48
CONECT   23   24   49   50
CONECT   24   25
CONECT   25   51   52   53
END

HMDB0004631
     RDKit          3D
Formebolone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.8639   -0.3534   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5079   -0.1712   -0.3807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3260   -1.0196    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.2400    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    1.6449    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    0.9095   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1220    0.7303    0.6295 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4597    2.0631    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    2.1016    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023    1.1075    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755    1.4770   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664    0.5657   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7752    0.9056   -1.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -0.7692   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8642   -1.7319   -1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3679   -2.8559   -2.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9214   -1.0997   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.2090    0.2183 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9375   -0.8514    1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    0.0177   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1225   -1.2473   -0.8983 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7252   -1.5477   -2.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -1.2095   -1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -0.4936   -0.0649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9690   -1.2419    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    0.2538   -2.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144    0.0330   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -1.4221   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.6475    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    1.9217   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    1.3127    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517    2.7464    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    1.2906    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660    1.2561   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    0.1234    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809    2.8102    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849    2.5193    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    1.8438    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    3.1185    1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2105    2.4928    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   -1.4337   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -2.1022   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -1.7030    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -1.2532    1.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -0.1185    2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639    0.7107   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.1122   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -2.1315   -2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -2.2534   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -0.7315   -2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.9122    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079   -1.9314    1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.6420    2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  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  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 14 17  2  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24  2  1  0
 24  6  1  0
 20  7  1  0
 18 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 15 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  6
 21 47  1  1
 22 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(11a,17b)-11,17-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehyde	HMDB
11a,17b-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehyde	HMDB
11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde	HMDB
2-Formyl-11a-hydroxy-D1-methyltestosterone	HMDB
2-Formyl-17a-methylandrosta-1,4-dien-11a,17b-diol-3-one	HMDB
2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-dihydroxy-3-one	HMDB
2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-one	HMDB
Esiclene	HMDB, MeSH
Formyldienolone	HMDB, MeSH
2-Formyl-17 alpha-methylandrosta-1,4-diene-11 alpha,17 beta-diol-3-one	MeSH, HMDB
Formyldienolone, (11 beta,17beta)-isomer	MeSH, HMDB
Formildienolone	MeSH, HMDB
Formebolone	MeSH

Chemical Formula

C₂₁H₂₈O₄

Average Molecular Weight

344.4446

Monoisotopic Molecular Weight

344.198759384

IUPAC Name

(1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-4-carbaldehyde

Traditional Name

formebolone

CAS Registry Number

2454-11-7

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C

InChI Identifier

InChI=1S/C21H28O4/c1-19-9-12(11-22)16(23)8-13(19)4-5-14-15-6-7-21(3,25)20(15,2)10-17(24)18(14)19/h8-9,11,14-15,17-18,24-25H,4-7,10H2,1-3H3/t14-,15-,17+,18+,19-,20-,21-/m0/s1

InChI Key

AMVODTGMYSRMNP-GNIMZFFESA-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-1,4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-alpha-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Cyclic ketone
Aldehyde
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
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: HMDB0004631)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0004631)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004631)

Source

Exogenous

Exogenous (HMDB: HMDB0004631)

Food

Food (HMDB: HMDB0004631)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004631)

Molecular messenger

Hormone (HMDB: HMDB0004631)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004631)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0004631)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	209 - 212 °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	0.06 g/L	ALOGPS
logP	2.59	ALOGPS
logP	1.76	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.39	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.9 m³·mol⁻¹	ChemAxon
Polarizability	38.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.948	31661259
DarkChem	[M-H]-	178.44	31661259
DeepCCS	[M-2H]-	210.833	30932474
DeepCCS	[M+Na]+	184.93	30932474
AllCCS	[M+H]+	184.0	32859911
AllCCS	[M+H-H2O]+	181.2	32859911
AllCCS	[M+NH4]+	186.5	32859911
AllCCS	[M+Na]+	187.3	32859911
AllCCS	[M-H]-	189.2	32859911
AllCCS	[M+Na-2H]-	189.5	32859911
AllCCS	[M+HCOO]-	189.9	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.	5.97 minutes	32390414
Predicted by Siyang on May 30, 2022	15.1243 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2748.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.6 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	756.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1191.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.1 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	1610.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	442.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	464.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	270.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	462.9 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	14.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Formebolone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C	4017.8	Standard polar	33892256
Formebolone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C	2857.5	Standard non polar	33892256
Formebolone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C	3253.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Formebolone,1TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)C(C=O)=C[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3226.4	Semi standard non polar	33892256
Formebolone,1TMS,isomer #2	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)C(C=O)=C[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3146.5	Semi standard non polar	33892256
Formebolone,2TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)C(C=O)=C[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3128.8	Semi standard non polar	33892256
Formebolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@]1(C)CC[C@H]2[C@@H]3CCC4=CC(=O)C(C=O)=C[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3460.1	Semi standard non polar	33892256
Formebolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@]2(C)[C@@H](CC[C@]2(C)O)[C@@H]2CCC3=CC(=O)C(C=O)=C[C@]3(C)[C@H]21	3389.6	Semi standard non polar	33892256
Formebolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@]2(C)[C@@H](CC[C@]2(C)O[Si](C)(C)C(C)(C)C)[C@@H]2CCC3=CC(=O)C(C=O)=C[C@]3(C)[C@H]21	3583.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Formebolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-1549000000-42102185d1dded40ecea	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formebolone GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3506900000-e9c4f9b646ae0846ac95	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formebolone 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 - Formebolone 10V, Positive-QTOF	splash10-056r-0009000000-83d05b9ec6d4114e8a0c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 20V, Positive-QTOF	splash10-0a6r-0239000000-e2958d7b5f276c7c8f72	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 40V, Positive-QTOF	splash10-0rkd-2294000000-a7c54e1065ffa26a8568	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 10V, Negative-QTOF	splash10-0006-0009000000-be5664450200906ba6e6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 20V, Negative-QTOF	splash10-002f-0009000000-51507deb2305cd3590af	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 40V, Negative-QTOF	splash10-01ta-1196000000-a3d80644f38949e4fd48	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 10V, Negative-QTOF	splash10-0006-0009000000-132e2debff844207d185	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 20V, Negative-QTOF	splash10-0006-0019000000-440aecd91bd6be86b2b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 40V, Negative-QTOF	splash10-0002-0293000000-688a79dea37f10a0d946	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 10V, Positive-QTOF	splash10-002b-0019000000-4d6ca44432cd0e2ca971	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 20V, Positive-QTOF	splash10-000e-3954000000-ac54633877d9786e5126	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formebolone 40V, Positive-QTOF	splash10-000i-4890000000-b21d6e58b198bff27fda	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

DB01569

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023388

KNApSAcK ID

Not Available

Chemspider ID

16234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Formebolone

METLIN ID

Not Available

PubChem Compound

17150

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

Canonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.

Material Safety Data Sheet (MSDS)

Not Available

General References

Thevis M, Schanzer W: Examples of doping control analysis by liquid chromatography-tandem mass spectrometry: ephedrines, beta-receptor blocking agents, diuretics, sympathomimetics, and cross-linked hemoglobins. J Chromatogr Sci. 2005 Jan;43(1):22-31. [PubMed:15808003 ]

Showing metabocard for Formebolone (HMDB0004631)

MOL for HMDB0004631 (Formebolone)

3D MOL for HMDB0004631 (Formebolone)

3D SDF for HMDB0004631 (Formebolone)

3D-SDF for HMDB0004631 (Formebolone)

PDB for HMDB0004631 (Formebolone)

3D PDB for HMDB0004631 (Formebolone)

SMILES for HMDB0004631 (Formebolone)

INCHI for HMDB0004631 (Formebolone)

Structure for HMDB0004631 (Formebolone)

3D Structure for HMDB0004631 (Formebolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra