16-Epiestriol
Basic information
- CAS
547-81-9- Standard SMILES
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C[C@H](O)[C@@H]2O- InChIKey
PROQIPRRNZUXQM-ZMSHIADSSA-N- Molecular formula
- C18H24O3
- Average molar mass
- 288.4 g/mol
- Monoisotopic mass
- 288.17254462
Overview
16beta-hydroxyestradiol is a 3-hydroxy steroid that is 17beta-estradiol substituted by a beta-hydroxy group at position 16. It has a role as an anti-inflammatory drug and a human xenobiotic metabolite. It is a 16beta-hydroxy steroid, a phenolic steroid, a member of phenols, a 17beta-hydroxy steroid and a 3-hydroxy steroid. It is functionally related to a 17beta-estradiol. It derives from a hydride of an estrane.
Names & identifiers
- Preferred name
- 16-Epiestriol
- IUPAC
- (8R,9S,13S,14S,16S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
- English name
- 16-EPIESTRIOL
- Molecular formula
- C18H24O3
- Molecular weight
- 288.38
Names & synonyms
16-EpiestriolEpiestriol547-81-9EpioestriolEpiestriolumEpioestriolumEpiestriolo(8R,9S,13S,14S,16S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triolNSC-266468XZ32LI44KEstra-1,3,5(10)-triene-3,16beta,17beta-triolNSC-758892
Show more names
16β-hydroxyestradiolNSC 26646Isostriol16β-Oestriol16-EPISTRIOL16-epioestriol
(8R,9S,13S,14S,16S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthrene-3,16,17-triolRefChem:590931208-937-9ActriolEstriol EP Impurity F16-epi-Estriol16b-hydroxyestradiol16-Epiestratriol
Database identifiers
- CAS
547-81-9- PubChem CID
- 68929
- DTXSID
DTXSID10894790- ChEMBL
CHEMBL1908074
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 60.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 411
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Collision Cross Section
153.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.53 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 289 · 289-2910C
- Boiling point
- 370.61 °C · 370.61°C (rough estimate)
- Density
- 1.1285 · 1.1285 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Heated)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H350 (50%): May cause cancer [Danger Carcinogenicity]
P203, P260, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesCarc. 1A (50%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H360
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
Usesestrogen
Uses16-Epiestriol is a metabolite of Estradiol.
Additional notes
DefinitionChEBI: A 3-hydroxy steroid that is 17beta-estradiol substituted by a beta-hydroxy group at position 16.
Suppliers
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Compound notes
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