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

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:14 UTC
Update Date2020-06-04 18:57:31 UTC
BMDB IDBMDB0063610
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
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2590000000-2d3f8090ffa4733bf9eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2590000000-2d3f8090ffa4733bf9eeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-3190000000-3e8980db36b0ac7be7c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-a8fe8b7a30127f18cfcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0029000000-b5f28037c9691eb24047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-0790000000-fe84d84c9218b8196292View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-eddb407ee0b99900a0ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0229000000-967d4bba6420d7542b78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-0390000000-de32116845b75e0077f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-3c403b01150c1ceb1813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0091000000-a71d76ec2ab1019a4927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0290000000-251e3f81d8a1025f4436View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-90d3b740113c4fec06c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-1096000000-d8dfb53c7c6dd6d1051aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9160000000-978ead17186c9fd3851cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-2690000000-770065ddc57899130a31View in MoNA
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 50.32 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.00250 +/- 0.00750 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0259550
DrugBank IDDB00648
Phenol Explorer Compound IDNot Available
FooDB 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 ]