Showing metabocard for 4-Chloromethandienone (BMDB0004634)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:57 UTC
Update Date2020-04-22 15:13:57 UTC
BMDB IDBMDB0004634
Secondary Accession Numbers
  • BMDB04634
Metabolite Identification
Common Name4-Chloromethandienone
Description4-Chloromethandienone, also known as CDMT or oral turinabol, 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. Based on a literature review very few articles have been published on 4-Chloromethandienone.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 - 127 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06di-2359000000-29ca0d52c8fd70fc30d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004l-5249000000-9650931bf7b8f174feaeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-4d48d5496c111810a053View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0298000000-37b2f0f935b6a78a8bb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7c-4593000000-492a05f7e32939505e60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-80bda444bab1f625c66aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-17287ea8d4e89a4ee477View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017j-0094000000-d1ada8f9f78231dd96f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-9ddc118eccb9db975822View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9004000000-9a783b35f47e53ab4eb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9072000000-7ac5075eb9109bfda145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-c2e40146619d50f32d69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1973000000-ea8ac005cf57c5cd7c8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-2590000000-1f06ae27f07b88dfa774View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004634
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
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 ReferencesNot Available