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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 22:45:16 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004634
Secondary Accession Numbers
  • HMDB04634
Metabolite Identification
Common Name4-Chloromethandienone
Description4-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
Data?1582752310
Synonyms
ValueSource
4-Chloro-methandienoneMeSH
CDMTMeSH
D-4-Chloro-17 beta-hydroxy-3-oxo-17 alpha-methylandrosta-1,4-dieneMeSH
Oral turinabolMeSH
Turinabol-oralMeSH
DehydrochlormethyltestosteroneMeSH
(17b)-4-chloro-17-Hydroxy-17-methyl-androsta-1,4-dien-3-oneHMDB
1-dehydro-4-chloro-17-MethyltestosteroneHMDB
1-dehydro-4-chloro-17a-MethyltestosteroneHMDB
4-chloro-1,2-dehydro-17a-MethyltestosteroneHMDB
4-chloro-1-dehydro-17-MethyltestosteroneHMDB
4-chloro-1-DehydromethyltestosteroneHMDB
4-chloro-17a-Methyl-17b-hydroxyandrosta-1,4-dien-3-oneHMDB
4-chloro-17b-Hydroxy-17-methyl-androsta-1,4-dien-3-oneHMDB
4-chloro-17b-Hydroxy-17a-methyl-5a-androsta-1,4-dien-3-oneHMDB
4-ChlorodehydromethyltestosteroneHMDB
4-ChlorodianabolHMDB
Oral-turinabolHMDB
Chemical FormulaC20H27ClO2
Average Molecular Weight334.88
Monoisotopic Molecular Weight334.169957815
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 Nameoral turinabol
CAS Registry Number2446-23-3
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 KeyAGUNEISBPXQOPA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 - 127 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP4.11ALOGPS
logP4.03ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.95 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-206.47730932474
DeepCCS[M+Na]+180.81330932474
AllCCS[M+H]+180.432859911
AllCCS[M+H-H2O]+177.532859911
AllCCS[M+NH4]+183.032859911
AllCCS[M+Na]+183.832859911
AllCCS[M-H]-187.532859911
AllCCS[M+Na-2H]-187.732859911
AllCCS[M+HCOO]-188.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
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@]12C3624.9Standard polar33892256
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@]12C2650.7Standard non polar33892256
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@]12C3012.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Chloromethandienone,1TMS,isomer #1C[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)C2952.6Semi standard non polar33892256
4-Chloromethandienone,1TBDMS,isomer #1CC(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@@]21C3205.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Chloromethandienone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06di-2359000000-29ca0d52c8fd70fc30d52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Chloromethandienone GC-MS (1 TMS) - 70eV, Positivesplash10-004l-5249000000-9650931bf7b8f174feae2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Chloromethandienone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 10V, Negative-QTOFsplash10-001i-0009000000-80bda444bab1f625c66a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 20V, Negative-QTOFsplash10-001i-0009000000-17287ea8d4e89a4ee4772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 40V, Negative-QTOFsplash10-017j-0094000000-d1ada8f9f78231dd96f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 10V, Negative-QTOFsplash10-001i-0009000000-9ddc118eccb9db9758222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 20V, Negative-QTOFsplash10-001i-9004000000-9a783b35f47e53ab4eb42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 40V, Negative-QTOFsplash10-001i-9072000000-7ac5075eb9109bfda1452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 10V, Positive-QTOFsplash10-014r-0009000000-4d48d5496c111810a0532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 20V, Positive-QTOFsplash10-014r-0298000000-37b2f0f935b6a78a8bb22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 40V, Positive-QTOFsplash10-0f7c-4593000000-492a05f7e32939505e602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 10V, Positive-QTOFsplash10-00kr-0019000000-c2e40146619d50f32d692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 20V, Positive-QTOFsplash10-000i-1973000000-ea8ac005cf57c5cd7c8b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chloromethandienone 40V, Positive-QTOFsplash10-0a6r-2590000000-1f06ae27f07b88dfa7742021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023389
KNApSAcK IDNot Available
Chemspider ID88972
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorodehydromethyltestosterone
METLIN IDNot Available
PubChem Compound98521
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDu, 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
  1. 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 ]