Showing metabocard for o,p′-DDD (BMDB0063610)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:14 UTC
Update Date2020-06-04 18:57:31 UTC
MCDB ID BMDB0063610
Secondary Accession Numbers
  • BMDB63610
Metabolite Identification
Common Nameo,p′-DDD
DescriptionMitotane is a derivative of the insecticide dichlorodiphenyldichloroethane that specifically inhibits cells of the adrenal cortex and their production of hormones. It is used to treat adrenocortical tumors and causes CNS damage, but no bone marrow depression (PubChem). Its biochemical mechanism of action is unknown, although data are available to suggest that it modifies the peripheral metabolism of steroids as well as directly suppressing the adrenal cortex.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LysodrenKegg
Bristol myers squibb brand OF mitotaneMeSH, HMDB
KhloditanMeSH, HMDB
ortho,Para-DDDMeSH, HMDB
ChloditanMeSH, HMDB
Bristol-myers squibb brand OF mitotaneMeSH, HMDB
O,P-DDDMeSH, HMDB
ortho,Para DDDMeSH, HMDB
ChlodithaneMeSH, HMDB
MytotanMeSH, HMDB
Chemical FormulaC14H10Cl4
Average Molecular Weight320.041
Monoisotopic Molecular Weight317.953661148
IUPAC Name1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene
Traditional Namemitotane
CAS Registry Number53-19-0
SMILES
ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H
InChI KeyJWBOIMRXGHLCPP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.08ALOGPS
logP6.11ChemAxon
logS-7.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.97 m³·mol⁻¹ChemAxon
Polarizability29.93 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2590000000-2d3f8090ffa4733bf9ee2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2590000000-2d3f8090ffa4733bf9ee2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-3190000000-3e8980db36b0ac7be7c92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-a8fe8b7a30127f18cfcf2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0029000000-b5f28037c9691eb240472016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-0790000000-fe84d84c9218b81962922016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-eddb407ee0b99900a0ec2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0229000000-967d4bba6420d7542b782016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-0390000000-de32116845b75e0077f52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-3c403b01150c1ceb18132021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0091000000-a71d76ec2ab1019a49272021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0290000000-251e3f81d8a1025f44362021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-90d3b740113c4fec06c32021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-1096000000-d8dfb53c7c6dd6d1051a2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9160000000-978ead17186c9fd3851c2021-10-11View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-2690000000-770065ddc57899130a312014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.01 +/- 0.01 uM details
HMDB IDHMDB0259550
DrugBank IDDB00648
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4066
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMitotane
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16. [PubMed:17180431 ]