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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014786

Secondary Accession Numbers

HMDB14786

Metabolite Identification

Common Name

Mitotane

Description

Mitotane is only found in individuals that have used or taken this drug. It 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 the drug modifies the peripheral metabolism of steroids as well as directly suppressing the adrenal cortex.

Structure

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


  Mrv1652305271900222D          

 18 19  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  2  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014786

> <DATABASE_NAME>
hmdb

> <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_KEY>
JWBOIMRXGHLCPP-UHFFFAOYSA-N

> <FORMULA>
C14H10Cl4

> <MOLECULAR_WEIGHT>
320.041

> <EXACT_MASS>
317.953661148

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
29.934789412180983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
6.110364791333334

> <ALOGPS_LOGS>
-7.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
79.96540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.42e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mitotane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -9.336   3.850   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0      -1.334   8.470   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0      -2.667   9.240   0.000  0.00  0.00          Cl+0
HETATM   18 Cl   UNK     0      -5.335   9.240   0.000  0.00  0.00          Cl+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    5    6   13                                                  
CONECT   10    7    8   15                                                  
CONECT   11    3   12   13                                                  
CONECT   12    4   11   16                                                  
CONECT   13    9   11   14                                                  
CONECT   14   13   17   18                                                  
CONECT   15   10                                                            
CONECT   16   12                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0259550
HETATM    1 CL1  UNL     1       4.841  -2.438   0.919  1.00  0.00          CL  
HETATM    2  C1  UNL     1       3.476  -1.402   0.573  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.711  -1.684  -0.517  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.651  -0.904  -0.810  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.240   0.224  -0.064  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.066   1.007  -0.485  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.218   0.312  -0.278  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.029  -0.100  -1.355  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.219  -0.738  -1.219  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.698  -1.017   0.035  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.964  -0.647   1.125  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.744   0.008   0.946  1.00  0.00           C  
HETATM   13 CL2  UNL     1      -0.881   0.434   2.368  1.00  0.00          CL  
HETATM   14  C12 UNL     1       0.101   2.453  -0.256  1.00  0.00           C  
HETATM   15 CL3  UNL     1       0.251   3.052   1.390  1.00  0.00          CL  
HETATM   16 CL4  UNL     1      -1.148   3.322  -1.183  1.00  0.00          CL  
HETATM   17  C13 UNL     1       2.044   0.462   1.020  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.146  -0.324   1.351  1.00  0.00           C  
HETATM   19  H1  UNL     1       2.943  -2.530  -1.153  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.043  -1.136  -1.686  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.174   0.960  -1.642  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.692   0.099  -2.370  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.792  -1.026  -2.112  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.647  -1.526   0.133  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.342  -0.867   2.129  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.064   2.846  -0.735  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.863   1.274   1.668  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.760  -0.114   2.208  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   18
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6   17
CONECT    6    7   14   21
CONECT    7    8    8   12
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13
CONECT   14   15   16   26
CONECT   17   18   18   27
CONECT   18   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lysodren	Kegg
Bristol myers squibb brand OF mitotane	MeSH, HMDB
Khloditan	MeSH, HMDB
ortho,Para-DDD	MeSH, HMDB
Chloditan	MeSH, HMDB
Bristol-myers squibb brand OF mitotane	MeSH, HMDB
O,P-DDD	MeSH, HMDB
ortho,Para DDD	MeSH, HMDB
Chlodithane	MeSH, HMDB
Mytotan	MeSH, HMDB

Chemical Formula

C₁₄H₁₀Cl₄

Average Molecular Weight

320.041

Monoisotopic Molecular Weight

317.953661148

IUPAC Name

1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene

Traditional Name

mitotane

CAS Registry Number

53-19-0

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 Key

JWBOIMRXGHLCPP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	77 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9.4e-06 g/L	Not Available
LogP	6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.4e-06 g/L	ALOGPS
logP	6.08	ALOGPS
logP	6.11	ChemAxon
logS	-7.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.97 m³·mol⁻¹	ChemAxon
Polarizability	29.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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+H]+	159.555	30932474
DeepCCS	[M-H]-	157.197	30932474
DeepCCS	[M-2H]-	190.083	30932474
DeepCCS	[M+Na]+	165.648	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	166.0	32859911
AllCCS	[M-H]-	145.8	32859911
AllCCS	[M+Na-2H]-	145.0	32859911
AllCCS	[M+HCOO]-	144.3	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.	9.25 minutes	32390414
Predicted by Siyang on May 30, 2022	24.6494 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	94.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mitotane	ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl	3241.8	Standard polar	33892256
Mitotane	ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl	2129.3	Standard non polar	33892256
Mitotane	ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl	2182.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00648	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00648	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00648

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mitotane

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1150611

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

References

Lindhe O, Skogseid B, Brandt I: Cytochrome P450-catalyzed binding of 3-methylsulfonyl-DDE and o,p'-DDD in human adrenal zona fasciculata/reticularis. J Clin Endocrinol Metab. 2002 Mar;87(3):1319-26. [PubMed:11889204 ]

Enzyme Details

2. Adrenodoxin, mitochondrial precursor

General function:: Energy production and conversion
Specific function:: Participates in the synthesis of thyroid hormones. Transfers electrons from adrenodoxin reductase to the cholesterol side chain cleavage cytochrome P450
Gene Name:: FDX1
Uniprot ID:: P10109
Molecular weight:: 19393.0

References

Kandul SV, Iatsyk MI, Kononenko VIa: [Comparative study of the effect of chloditan on the concentration of cytochrome P-450 and adrenodoxin in various organs of the dog and rat]. Fiziol Zh. 1986 Sep-Oct;32(5):579-84. [PubMed:3770229 ]
Cabrini DA, Campos MM, Tratsk KS, Merino VF, Silva JA Jr, Souza GE, Avellar MC, Pesquero JB, Calixto JB: Molecular and pharmacological evidence for modulation of kinin B(1) receptor expression by endogenous glucocorticoids hormones in rats. Br J Pharmacol. 2001 Jan;132(2):567-77. [PubMed:11159707 ]
Cai W, Counsell RE, Schteingart DE, Sinsheimer JE, Vaz AD, Wotring LL: Adrenal proteins bound by a reactive intermediate of mitotane. Cancer Chemother Pharmacol. 1997;39(6):537-40. [PubMed:9118466 ]

Showing metabocard for Mitotane (HMDB0014786)

MOL for HMDB0014786 (Mitotane)

3D MOL for HMDB0014786 (Mitotane)

3D SDF for HMDB0014786 (Mitotane)

3D-SDF for HMDB0014786 (Mitotane)

PDB for HMDB0014786 (Mitotane)

3D PDB for HMDB0014786 (Mitotane)

SMILES for HMDB0014786 (Mitotane)

INCHI for HMDB0014786 (Mitotane)

Structure for HMDB0014786 (Mitotane)

3D Structure for HMDB0014786 (Mitotane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes

References

References