Estramustine (CED0005678)

Record Information
Version1.0
Creation Date2016-05-22 05:45:16 UTC
Update Date2026-08-22 01:33:55 UTC
SynCED IDCED0005678
Secondary Accession Numbers
  • CHEM019007
Identification
Common NameEstramustine
ClassSmall Molecule
Description
Estramustine is an organic compound with the formula C23H31Cl2NO3 and an average molecular weight of 440.40 g/mol. Estramustine belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. It is categorized as a lipid and lipid-like molecule. This compound is found in healthcare, pharmaceuticals, and veterinary products, where it is used as an antineoplastic agent. The recorded route of exposure for this substance is oral. Estramustine interacts with four recorded protein targets, acting as an agonist, antagonist, or other/unknown modulator of Estrogen receptor beta (ESR2), Estrogen receptor (ESR1), Microtubule-associated protein 2 (MAP2), and Microtubule-associated protein 1A (MAP1A).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
17beta-Estradiol 3-(bis(2-chloroethyl)carbamate)ChEBI
Estradiol 3-(N,N-bis(2-chloroethyl)carbamate)ChEBI
EstramustinaChEBI
EstramustinumChEBI
17b-Estradiol 3-(bis(2-chloroethyl)carbamate)Generator
17b-Estradiol 3-(bis(2-chloroethyl)carbamic acid)Generator
17beta-Estradiol 3-(bis(2-chloroethyl)carbamic acid)Generator
17Β-estradiol 3-(bis(2-chloroethyl)carbamate)Generator
17Β-estradiol 3-(bis(2-chloroethyl)carbamic acid)Generator
Estradiol 3-(N,N-bis(2-chloroethyl)carbamic acid)Generator
Estramustin sodium phosphateHMDB
Estramustine sodium phosphateHMDB
EstracytHMDB
Estramustine phosphate sodiumHMDB
Phosphate, estramustinHMDB
Leo 275HMDB
EmcytHMDB
EstramustinphosphateHMDB
Estramustin phosphateHMDB
Leo-275HMDB
Phosphate sodium, estramustineHMDB
Chemical FormulaC23H31Cl2NO3
Average Molecular Mass440.403 g/mol
Monoisotopic Mass439.168 g/mol
CAS Registry Number2998-57-4
IUPAC Name(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl N,N-bis(2-chloroethyl)carbamate
Traditional Nameestramustine
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
InChI KeyFRPJXPJMRWBBIH-RBRWEJTLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Nitrogen mustard
  • Benzenoid
  • Cyclic alcohol
  • Carbamic acid ester
  • Secondary alcohol
  • Carbonic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Alkyl chloride
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Alkyl halide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP4.97ALOGPS
logP5.1ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.21 m³·mol⁻¹ChemAxon
Polarizability48.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-7427900000-b87366cc1573c4f6c93aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-8704900000-9a612e46f22fe81c874cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-0720900000-7d95b1bd74a3e1ae6ae2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-2971100000-a6f224fc389435653942Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fu-9510000000-032d08f0be5c8b065fa7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0522900000-a880e700fad8ec3373b9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0v4i-0962500000-ffc041fb7d64ff64e5e8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h4o-7980000000-eef6a5c5a61126ea9699Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0020900000-c6017d6c0b19d376975cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01vo-0216900000-e073983c6de9895bcdc7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-5910000000-1c6900d7579dfbd1cc68Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0019-4002900000-5c59bbd62d2862fbf52dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9050000000-f5313068b0db56036aa5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-c2fa753da65a4bac80a1Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
269.0 Log mg/kg [150:480]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
CEDs000358Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentNot Available
CEDs000519Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.Electrical & Electronic EquipmentNot Available
CEDs000561Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.Household cleaning & consumer productsNot Available
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsNot Available
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingNot Available
CEDs000604Pest Attractants?Pest attractants are synthetic chemicals designed to lure specific pests for monitoring or control purposes.Agriculture & land managementNot Available
CEDs000606Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.Agriculture & land managementNot Available
CEDs000610Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.Personal care & cosmeticsNot Available
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsNot Available
CEDs000614Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.Personal care & cosmeticsNot Available
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsNot Available
CEDs000650Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.Textiles, leather & furnishingsNot Available
CEDs000667Gaseous Fire Fighting?Gaseous fire fighting systems utilize synthetic chemicals, such as halocarbons and inert gases, to suppress fires through chemical and physical processes.Fire suppression systems & agentsNot Available
CEDs000684Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.Building & ConstructionNot Available
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionNot Available
CEDs000692Silica Free Oxide Glass?Silica Free Oxide Glass is a type of glass that is produced using alternative materials to traditional silica-based formulations.Building & ConstructionNot Available
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingNot Available
CEDs000732Spectacle Cases?Spectacle cases can serve as a source of synthetic chemical contamination due to the materials used in their production, such as polycarbonate, PVC, and various plastics, which may leach harmful substances over time.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000739Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.Paper, pulp & fiber productsNot Available
CEDs000740Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.Paper, pulp & fiber productsNot Available
CEDs000741Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.Paper, pulp & fiber productsNot Available
CEDs000743Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.Wastewater, sanitation & biosolidsNot Available
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsNot Available
Pathways
1 pathwayPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Androgen receptor structureClick to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.543
Applicability Domain
0.672
Statistical Significance
2.90e-04
Supporting Reference Compounds
73
E-value
2.25763
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)
Prediction Confidence Score
0.521
Applicability Domain
0.672
Statistical Significance
1.80e-04
Supporting Reference Compounds
33
E-value
1.40129
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)
Prediction Confidence Score
0.517
Applicability Domain
0.672
Statistical Significance
5.30e-04
Supporting Reference Compounds
201
E-value
4.12601
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)
Prediction Confidence Score
0.513
Applicability Domain
0.672
Statistical Significance
0.0022
Supporting Reference Compounds
593
E-value
16.9711
Click to view 3D structureSolute carrier organic anion transporter family member 1A1P46720Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.493
Applicability Domain
0.645
Statistical Significance
6.00e-05
Supporting Reference Compounds
10
E-value
0.467095
Click to view 3D structureEstrogen sulfotransferaseQ95MF8Sus scrofaPredicted (SEA)
Prediction Confidence Score
0.493
Applicability Domain
0.493
Statistical Significance
7.00e-05
Supporting Reference Compounds
1
E-value
0.544945
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)
Prediction Confidence Score
0.482
Applicability Domain
0.672
Statistical Significance
2.10e-04
Supporting Reference Compounds
40
E-value
1.63483
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)
Prediction Confidence Score
0.452
Applicability Domain
0.593
Statistical Significance
7.30e-04
Supporting Reference Compounds
174
E-value
5.68299
Steryl-sulfatase structureClick to view 3D structureSteryl-sulfataseP08842HumansPredicted (SEA)
Prediction Confidence Score
0.436
Applicability Domain
0.471
Statistical Significance
1.20e-04
Supporting Reference Compounds
14
E-value
0.934191
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)
Prediction Confidence Score
0.428
Applicability Domain
0.593
Statistical Significance
5.80e-04
Supporting Reference Compounds
21
E-value
4.51525
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)
Prediction Confidence Score
0.423
Applicability Domain
0.672
Statistical Significance
0.0018
Supporting Reference Compounds
154
E-value
13.8572
17-beta-hydroxysteroid dehydrogenase type 1 structureClick to view 3D structure17-beta-hydroxysteroid dehydrogenase type 1P14061HumansPredicted (SEA)
Prediction Confidence Score
0.398
Applicability Domain
0.425
Statistical Significance
7.40e-04
Supporting Reference Compounds
42
E-value
5.76084
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)
Prediction Confidence Score
0.396
Applicability Domain
0.471
Statistical Significance
0.008
Supporting Reference Compounds
472
E-value
62.3572
Click to view 3D structureSolute carrier family 22 member 3O88446Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.371
Applicability Domain
0.593
Statistical Significance
1.60e-04
Supporting Reference Compounds
3
E-value
1.24559
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)
Prediction Confidence Score
0.367
Applicability Domain
0.672
Statistical Significance
0.014
Supporting Reference Compounds
686
E-value
109.3
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)
Prediction Confidence Score
0.365
Applicability Domain
0.593
Statistical Significance
0.0037
Supporting Reference Compounds
146
E-value
28.7264
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)
Prediction Confidence Score
0.345
Applicability Domain
0.471
Statistical Significance
0.0146
Supporting Reference Compounds
372
E-value
113.348
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)
Prediction Confidence Score
0.338
Applicability Domain
0.593
Statistical Significance
0.0023
Supporting Reference Compounds
49
E-value
18.2167
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)
Prediction Confidence Score
0.332
Applicability Domain
0.403
Statistical Significance
0.0049
Supporting Reference Compounds
127
E-value
38.1461
Multidrug resistance-associated protein 1 structureClick to view 3D structureMultidrug resistance-associated protein 1P33527HumansPredicted (SEA)
Prediction Confidence Score
0.32
Applicability Domain
0.645
Statistical Significance
0.002
Supporting Reference Compounds
49
E-value
15.2584
Polyunsaturated fatty acid lipoxygenase ALOX15 structureClick to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P12530Oryctolagus cuniculusPredicted (SEA)
Prediction Confidence Score
0.313
Applicability Domain
0.439
Statistical Significance
9.40e-04
Supporting Reference Compounds
47
E-value
7.31783
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)
Prediction Confidence Score
0.312
Applicability Domain
0.457
Statistical Significance
0.0279
Supporting Reference Compounds
451
E-value
216.966
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)
Prediction Confidence Score
0.305
Applicability Domain
0.471
Statistical Significance
0.0342
Supporting Reference Compounds
407
E-value
266.322
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)
Prediction Confidence Score
0.304
Applicability Domain
0.346
Statistical Significance
0.004
Supporting Reference Compounds
74
E-value
31.2954
Solute carrier family 22 member 1 structureClick to view 3D structureSolute carrier family 22 member 1O15245HumansPredicted (SEA)
Prediction Confidence Score
0.302
Applicability Domain
0.593
Statistical Significance
4.80e-04
Supporting Reference Compounds
30
E-value
3.73676
Concentrations
Not Available
External Links
DrugBank IDDB01196
HMDB IDHMDB0015327
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEstramustine
Chemspider ID227635
ChEBI ID4868
PubChem Compound ID259331
Kegg Compound IDC11228
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available