Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014414
Secondary Accession Numbers
  • HMDB14414
Metabolite Identification
Common NameChlorotrianisene
DescriptionChlorotrianisene is only found in individuals that have used or taken this drug. It is a powerful synthetic, non-steroidal estrogen.Chlorotrianisene binds to the estrogen receptor on various estrogen receptor bearing cells. Target cells include cells in the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.
Structure
Data?1582753176
Synonyms
ValueSource
ChloortrianisestrolChEBI
ChlorestroloChEBI
ChlorotrianisenumChEBI
ChlorotrianisineChEBI
ChlorotrianizenChEBI
ChlortrianisenChEBI
ChlortrianisestrolChEBI
ChlortrianisoestrolumChEBI
ChlortrianizenChEBI
ClorotrianisenoChEBI
TACEKegg
ChlortrianiseneHMDB
ChlortrianisenumHMDB
Chemical FormulaC23H21ClO3
Average Molecular Weight380.864
Monoisotopic Molecular Weight380.117922245
IUPAC Name1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
Traditional Namechlorotrianisene
CAS Registry Number569-57-3
SMILES
COC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1
InChI Identifier
InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
InChI KeyBFPSDSIWYFKGBC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Chloroalkene
  • Haloalkene
  • Ether
  • Vinyl halide
  • Vinyl chloride
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point115 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0002 g/LNot Available
LogP6.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0002 g/LALOGPS
logP5.95ALOGPS
logP5.43ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.17 m³·mol⁻¹ChemAxon
Polarizability41.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.35630932474
DeepCCS[M-H]-188.99830932474
DeepCCS[M-2H]-223.230932474
DeepCCS[M+Na]+198.42830932474
AllCCS[M+H]+190.932859911
AllCCS[M+H-H2O]+187.832859911
AllCCS[M+NH4]+193.832859911
AllCCS[M+Na]+194.632859911
AllCCS[M-H]-187.332859911
AllCCS[M+Na-2H]-186.632859911
AllCCS[M+HCOO]-185.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorotrianiseneCOC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C14487.9Standard polar33892256
ChlorotrianiseneCOC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C13085.8Standard non polar33892256
ChlorotrianiseneCOC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C13114.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlorotrianisene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00p1-0149000000-13ed744e89313692e56d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorotrianisene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorotrianisene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorotrianisene LC-ESI-qTof , Positive-QTOFsplash10-0udi-3900000000-f12188734d2d15075e1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorotrianisene , positive-QTOFsplash10-0012-1495000000-9f658a59776206767e092017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 10V, Positive-QTOFsplash10-001i-0009000000-be4271b6e19a1b13adf62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 20V, Positive-QTOFsplash10-001i-0009000000-7b589a415fcb543956f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 40V, Positive-QTOFsplash10-0uk9-1029000000-ff4c7067465507a37f162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 10V, Negative-QTOFsplash10-004i-0009000000-6015a236cb70e1e039be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 20V, Negative-QTOFsplash10-004i-0009000000-dcba52e7b835de4e3c352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 40V, Negative-QTOFsplash10-00r2-1019000000-3a45e45db259e4ec3ec22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 10V, Negative-QTOFsplash10-004i-0009000000-227ef4ce22c7135136812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 20V, Negative-QTOFsplash10-003r-9007000000-8be37b9c355ad83aa7732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 40V, Negative-QTOFsplash10-001i-9033000000-47370036c76681ebf7ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 10V, Positive-QTOFsplash10-001i-0009000000-4593fdf08237350f31072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 20V, Positive-QTOFsplash10-001i-0319000000-d2744fc9f6e8ad8e20bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorotrianisene 40V, Positive-QTOFsplash10-004i-0944000000-01b58af46de2630781862021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00269 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00269 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00269
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10815
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorotrianisene
METLIN IDNot Available
PubChem Compound11289
PDB IDNot Available
ChEBI ID3641
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Adashi EY, Hsueh AJ: Estrogens augment the stimulation of ovarian aromatase activity by follicle-stimulating hormone in cultured rat granulosa cells. J Biol Chem. 1982 Jun 10;257(11):6077-83. [PubMed:6804461 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4
References
  1. Kupfer D, Bulger WH: Inactivation of the uterine estrogen receptor binding of estradiol during P-450 catalyzed metabolism of chlorotrianisene (TACE). Speculation that TACE antiestrogenic activity involves covalent binding to the estrogen receptor. FEBS Lett. 1990 Feb 12;261(1):59-62. [PubMed:2307235 ]
  2. Jordan VC, Gosden B: Inhibition of the uterotropic activity of estrogens and antiestrogens by the short acting antiestrogen LY117018. Endocrinology. 1983 Aug;113(2):463-8. [PubMed:6872937 ]
  3. Wang JY, Xu BH, Tian LJ, Wang Y: [Clinical characteristics and potential prognostic factors of breast cancer patients with liver metastases]. Zhonghua Zhong Liu Za Zhi. 2006 Aug;28(8):612-6. [PubMed:17236558 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]