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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 22:45:16 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004634

Secondary Accession Numbers

HMDB04634

Metabolite Identification

Common Name

4-Chloromethandienone

Description

4-Chloromethandienone is a synthetic anabolic steroid, suspected of misuse in sports. Although the widespread use of androgenic anabolic steroids might be implicated in the development of hormone-sensitive tumors, there are few reports regarding a possible causal relation between doping and cancer; however, there is one reported case of a 32-year-old man that underwent right radical orchiectomy for a tumor (identified as an intratesticular leiomyosarcoma) of the upper pole of the right testicle where the patient reported a 5-year history of systematic use of high dose of 4-Chloromethandienone. (PMID: 10526287 ).

Structure

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


  Mrv0541 02231219572D          

 26 29  0  0  1  0            999 V2000
   20.7276  -21.4148    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.2215  -17.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2331  -20.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6825  -18.0338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6825  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -19.2714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2535  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4632  -17.7824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -17.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4632  -19.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2535  -18.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9447  -18.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5028  -19.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9813  -20.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6374  -17.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2404  -20.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4962  -20.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4124  -17.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5091  -18.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7381  -18.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7244  -20.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9561  -19.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9492  -20.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9777  -19.4701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4744  -19.7547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8252  -18.5288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  8  2  1  1  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 24  1  6  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 25  1  1  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  7 26  1  6  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  1  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END

HMDB0004634
     RDKit          3D
4-Chloromethandienone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.1898    0.2946    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.5404    0.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8886    1.8388   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957    2.0409   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6449    0.9014   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109    1.0911   -2.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.4151   -1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8703   -1.7879   -1.9962 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543   -0.5844   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779   -1.9550   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -1.9328   -0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -0.7671    0.1049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8224    0.4855   -0.4300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0673    1.7331   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748    1.5365   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    0.4341    0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7766    0.6693    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -0.8739   -0.1653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9967   -1.8408    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -1.2947    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.0698    0.0127 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6867   -0.1678   -1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633    0.9637    0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -0.7635    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    0.7838    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780    0.8117    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    2.6999    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4293    3.0457   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5673   -2.4144    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7959   -2.6423   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528   -2.8961   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -1.7452   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031   -0.9487    1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    0.3988   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    2.5493   -0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    2.0593    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431    2.4882   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3360    1.2690   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110    0.4452    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748    1.7544    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798    0.1027    2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055   -1.0577   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771   -2.8785    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -1.7705    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105   -1.2081    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211   -1.9748    0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9098    0.0906   -2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6150    0.4048   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -1.2410   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8400    1.6578    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  1
  9  2  1  0
 18 12  1  0
 13  2  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  1
 13 34  1  6
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
M  END


  Mrv0541 02231219572D          

 26 29  0  0  1  0            999 V2000
   20.7276  -21.4148    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.2215  -17.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2331  -20.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6825  -18.0338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6825  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -19.2714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2535  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4632  -17.7824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -17.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4632  -19.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2535  -18.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9447  -18.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5028  -19.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9813  -20.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6374  -17.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2404  -20.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4962  -20.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4124  -17.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5091  -18.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7381  -18.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7244  -20.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9561  -19.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9492  -20.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9777  -19.4701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4744  -19.7547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8252  -18.5288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  8  2  1  1  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 24  1  6  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 25  1  1  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  7 26  1  6  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  1  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004634

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

> <INCHI_KEY>
AGUNEISBPXQOPA-XMUHMHRVSA-N

> <FORMULA>
C20H27ClO2

> <MOLECULAR_WEIGHT>
334.88

> <EXACT_MASS>
334.169957815

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.264815916736396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
4.032775772333333

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5280914180307591

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
94.95259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oral turinabol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0004634
     RDKit          3D
4-Chloromethandienone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.1898    0.2946    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.5404    0.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8886    1.8388   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957    2.0409   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6449    0.9014   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109    1.0911   -2.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.4151   -1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8703   -1.7879   -1.9962 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543   -0.5844   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779   -1.9550   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -1.9328   -0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -0.7671    0.1049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8224    0.4855   -0.4300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0673    1.7331   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748    1.5365   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    0.4341    0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7766    0.6693    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -0.8739   -0.1653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9967   -1.8408    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -1.2947    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.0698    0.0127 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6867   -0.1678   -1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633    0.9637    0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -0.7635    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    0.7838    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780    0.8117    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    2.6999    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4293    3.0457   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5673   -2.4144    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7959   -2.6423   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528   -2.8961   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -1.7452   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031   -0.9487    1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    0.3988   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    2.5493   -0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    2.0593    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431    2.4882   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3360    1.2690   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110    0.4452    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748    1.7544    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798    0.1027    2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055   -1.0577   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771   -2.8785    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -1.7705    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105   -1.2081    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211   -1.9748    0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9098    0.0906   -2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6150    0.4048   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -1.2410   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8400    1.6578    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  1
  9  2  1  0
 18 12  1  0
 13  2  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  1
 13 34  1  6
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      38.692 -39.974   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      47.080 -32.880   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.902 -38.364   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      44.207 -33.663   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.207 -35.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.874 -35.973   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.540 -35.203   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.665 -33.194   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      42.874 -32.893   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.665 -35.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.540 -33.663   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.563 -34.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.139 -35.984   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.898 -37.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.123 -32.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      41.515 -38.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.126 -37.588   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      45.570 -31.855   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.150 -34.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.711 -35.115   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.686 -38.434   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.251 -35.928   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.239 -37.599   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      44.758 -36.344   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      43.819 -36.875   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      42.607 -34.587   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    8                                                            
CONECT    3   23                                                            
CONECT    4    5    8    9   15                                             
CONECT    5    4    6   10   24                                             
CONECT    6    5    7   14   25                                             
CONECT    7    6   11   13   26                                             
CONECT    8    2    4   12   18                                             
CONECT    9    4   11                                                       
CONECT   10    5   12                                                       
CONECT   11    7    9                                                       
CONECT   12    8   10                                                       
CONECT   13    7   17   19   20                                             
CONECT   14    6   16                                                       
CONECT   15    4                                                            
CONECT   16   14   17                                                       
CONECT   17   13   16   21                                                  
CONECT   18    8                                                            
CONECT   19   13                                                            
CONECT   20   13   22                                                       
CONECT   21    1   17   23                                                  
CONECT   22   20   23                                                       
CONECT   23    3   21   22                                                  
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0004634
HETATM    1  C1  UNL     1      -2.190   0.295   1.639  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.257   0.540   0.120  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.889   1.839  -0.060  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.996   2.041  -0.744  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.645   0.901  -1.369  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.711   1.091  -2.027  1.00  0.00           O  
HETATM    7  C6  UNL     1      -4.057  -0.415  -1.222  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -4.870  -1.788  -1.996  1.00  0.00          CL  
HETATM    9  C7  UNL     1      -2.954  -0.584  -0.536  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.378  -1.955  -0.420  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.877  -1.933  -0.625  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.216  -0.767   0.105  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.822   0.485  -0.430  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.067   1.733  -0.107  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.375   1.536  -0.531  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.926   0.434   0.282  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.777   0.669   1.752  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.257  -0.874  -0.165  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.997  -1.841   0.691  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.432  -1.295   0.718  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.359   0.070   0.013  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.687  -0.168  -1.423  1.00  0.00           C  
HETATM   23  O2  UNL     1       4.263   0.964   0.553  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.303  -0.763   1.889  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.309   0.784   2.054  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.078   0.812   2.106  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.421   2.700   0.397  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.429   3.046  -0.846  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.567  -2.414   0.568  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.796  -2.642  -1.184  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.453  -2.896  -0.332  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.699  -1.745  -1.712  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.403  -0.949   1.182  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.924   0.399  -1.533  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.490   2.549  -0.740  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.160   2.059   0.928  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.943   2.488  -0.463  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.336   1.269  -1.612  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.711   0.445   2.309  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.575   1.754   1.949  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.980   0.103   2.241  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.505  -1.058  -1.211  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.977  -2.879   0.321  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.600  -1.770   1.724  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.811  -1.208   1.737  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.121  -1.975   0.168  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.910   0.091  -2.141  1.00  0.00           H  
HETATM   48  H25 UNL     1       4.615   0.405  -1.718  1.00  0.00           H  
HETATM   49  H26 UNL     1       3.965  -1.241  -1.641  1.00  0.00           H  
HETATM   50  H27 UNL     1       3.840   1.658   1.119  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    9   13
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6    6    7
CONECT    7    8    9    9
CONECT    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   18   33
CONECT   13   14   34
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   17   18   21
CONECT   17   39   40   41
CONECT   18   19   42
CONECT   19   20   43   44
CONECT   20   21   45   46
CONECT   21   22   23
CONECT   22   47   48   49
CONECT   23   50
END

HMDB0004634
     RDKit          3D
4-Chloromethandienone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.1898    0.2946    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.5404    0.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8886    1.8388   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957    2.0409   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6449    0.9014   -1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7109    1.0911   -2.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.4151   -1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8703   -1.7879   -1.9962 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543   -0.5844   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779   -1.9550   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -1.9328   -0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -0.7671    0.1049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8224    0.4855   -0.4300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0673    1.7331   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748    1.5365   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    0.4341    0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7766    0.6693    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -0.8739   -0.1653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9967   -1.8408    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -1.2947    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.0698    0.0127 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6867   -0.1678   -1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633    0.9637    0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -0.7635    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    0.7838    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780    0.8117    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    2.6999    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4293    3.0457   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5673   -2.4144    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7959   -2.6423   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528   -2.8961   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -1.7452   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031   -0.9487    1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    0.3988   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    2.5493   -0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    2.0593    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431    2.4882   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3360    1.2690   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110    0.4452    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748    1.7544    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798    0.1027    2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055   -1.0577   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771   -2.8785    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -1.7705    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105   -1.2081    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211   -1.9748    0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9098    0.0906   -2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6150    0.4048   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -1.2410   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8400    1.6578    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  1
  9  2  1  0
 18 12  1  0
 13  2  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  1
 13 34  1  6
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Chloro-methandienone	MeSH
CDMT	MeSH
D-4-Chloro-17 beta-hydroxy-3-oxo-17 alpha-methylandrosta-1,4-diene	MeSH
Oral turinabol	MeSH
Turinabol-oral	MeSH
Dehydrochlormethyltestosterone	MeSH
(17b)-4-chloro-17-Hydroxy-17-methyl-androsta-1,4-dien-3-one	HMDB
1-dehydro-4-chloro-17-Methyltestosterone	HMDB
1-dehydro-4-chloro-17a-Methyltestosterone	HMDB
4-chloro-1,2-dehydro-17a-Methyltestosterone	HMDB
4-chloro-1-dehydro-17-Methyltestosterone	HMDB
4-chloro-1-Dehydromethyltestosterone	HMDB
4-chloro-17a-Methyl-17b-hydroxyandrosta-1,4-dien-3-one	HMDB
4-chloro-17b-Hydroxy-17-methyl-androsta-1,4-dien-3-one	HMDB
4-chloro-17b-Hydroxy-17a-methyl-5a-androsta-1,4-dien-3-one	HMDB
4-Chlorodehydromethyltestosterone	HMDB
4-Chlorodianabol	HMDB
Oral-turinabol	HMDB

Chemical Formula

C₂₀H₂₇ClO₂

Average Molecular Weight

334.88

Monoisotopic Molecular Weight

334.169957815

IUPAC Name

(1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Traditional Name

oral turinabol

CAS Registry Number

2446-23-3

SMILES

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

InChI Identifier

InChI=1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

InChI Key

AGUNEISBPXQOPA-XMUHMHRVSA-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
17-hydroxysteroid
4-halo-steroid
Halo-steroid
Oxosteroid
Hydroxysteroid
Delta-1,4-steroid
Alpha-haloketone
Alpha-chloroketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
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: HMDB0004634)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0004634)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004634)

Source

Exogenous

Exogenous (HMDB: HMDB0004634)

Food

Food (HMDB: HMDB0004634)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004634)

Molecular messenger

Hormone (HMDB: HMDB0004634)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004634)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 - 127 °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	0.0058 g/L	ALOGPS
logP	4.11	ALOGPS
logP	4.03	ChemAxon
logS	-4.8	ALOGPS
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	94.95 m³·mol⁻¹	ChemAxon
Polarizability	37.26 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
DeepCCS	[M-2H]-	206.477	30932474
DeepCCS	[M+Na]+	180.813	30932474
AllCCS	[M+H]+	180.4	32859911
AllCCS	[M+H-H2O]+	177.5	32859911
AllCCS	[M+NH4]+	183.0	32859911
AllCCS	[M+Na]+	183.8	32859911
AllCCS	[M-H]-	187.5	32859911
AllCCS	[M+Na-2H]-	187.7	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.	7.73 minutes	32390414
Predicted by Siyang on May 30, 2022	18.9515 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2647.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	549.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	224.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	250.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	872.3 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	840.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1576.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	511.5 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	1621.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	578.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	470.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	648.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Chloromethandienone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C	3624.9	Standard polar	33892256
4-Chloromethandienone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C	2650.7	Standard non polar	33892256
4-Chloromethandienone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C	3012.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Chloromethandienone,1TMS,isomer #1	C[C@]12C=CC(=O)C(Cl)=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O[Si](C)(C)C	2952.6	Semi standard non polar	33892256
4-Chloromethandienone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@]1(C)CC[C@H]2[C@@H]3CCC4=C(Cl)C(=O)C=C[C@]4(C)[C@H]3CC[C@@]21C	3205.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023389

KNApSAcK ID

Not Available

Chemspider ID

88972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorodehydromethyltestosterone

METLIN ID

Not Available

PubChem Compound

98521

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

Du, Hongwu; Lu, Yuan; Yang, Weiping; Wu, Moutian; Wang, Jun; Zhao, Shan; Pan, Mangeng; Cheng, Jing. Preparation of Steroid Antibodies and Parallel Detection of Multianabolic Steroid Abuse with Conjugated Hapten Microarray. Analytical Chemistry (2004), 76(20), 6166-6171.

Material Safety Data Sheet (MSDS)

Not Available

General References

Froehner M, Fischer R, Leike S, Hakenberg OW, Noack B, Wirth MP: Intratesticular leiomyosarcoma in a young man after high dose doping with Oral-Turinabol: a case report. Cancer. 1999 Oct 15;86(8):1571-5. [PubMed:10526287 ]

Showing metabocard for 4-Chloromethandienone (HMDB0004634)

MOL for HMDB0004634 (4-Chloromethandienone)

3D MOL for HMDB0004634 (4-Chloromethandienone)

3D SDF for HMDB0004634 (4-Chloromethandienone)

3D-SDF for HMDB0004634 (4-Chloromethandienone)

PDB for HMDB0004634 (4-Chloromethandienone)

3D PDB for HMDB0004634 (4-Chloromethandienone)

SMILES for HMDB0004634 (4-Chloromethandienone)

INCHI for HMDB0004634 (4-Chloromethandienone)

Structure for HMDB0004634 (4-Chloromethandienone)

3D Structure for HMDB0004634 (4-Chloromethandienone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized