2-Methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Basic information
- CAS
362-07-2- Standard SMILES
COc1cc2c(cc1O)CCC1C2CCC2(C)C(O)CCC12- InChIKey
CQOQDQWUFQDJMK-UHFFFAOYSA-N- Molecular formula
- C19H26O3
- Average molar mass
- 302.4 g/mol
- Monoisotopic mass
- 302.18819469
Overview
2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol is a steroid. It has a role as an estrogen.
Names & identifiers
- Preferred name
- 2-Methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
- IUPAC
- 2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
- English name
- 2-Methoxyestradiol
- Molecular formula
- C19H26O3
- Molecular weight
- 302.41
Names & synonyms
2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol2-ME2;NSC-6598532-Hydroxyestradiol 2-methyl-13C,d3-ether, 2-Methoxy-13C,d3-estradiol, 3,17beta-Dihydroxy-2-methoxy-13C,d3-1,3,5(10)-estratriene, 2,3,17beta-Trihydroxy-1,3,5(10)-estratriene-2-methyl-13C,d3-ether, 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl-13C,d3-ether2-Methoxy-.beta.-estradiolNSC6598532-Methoxy-b-estradiolNeuro_0003852-Methoxy-17alpha-estradiolCHEMBL23576SCHEMBL13123068CHEBI:110165HMS3268G22
Show more names
2-MeOE22-Methoxy-β-estradiol2-Methoxy 17β-Estradiol2-ME2PanzemNSC 659853Methoxy estradiol7-Methoxyestradiol2-Methoxyestradiol2-METHOXYOESTRADIOL
HMS5079M19s1233AKOS015967320ICX56088862-Methoxyestra-1(10),2,4-triene-3,17-diol2-Methoxyestra-1,3,5(10)-triene-3,17.beta.-diolBRD-A79248021-001-01-1Q27189546
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 49.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 425
Physicochemical properties
- Melting point
- 188 · 188-190°C
- Boiling point
- 464.4 · 464.4±45.0 °C(Predicted)
- Density
- 1.178 · 1.178±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 10 mg/mL · DMSO: 10 mg/mL
- form
- crystalline
- pka
- 10.29 · 10.29±0.60(Predicted)
- color
- light yellow
- λmax
- 286 nm · 286nm(EtOH)(lit.)
- InChI
- InChI=1/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/s3
- InChIKey
- CQOQDQWUFQDJMK-SSTWWWIQSA-N
- SMILES
- C[C@@]12[C@H](CC[C@@]1([H])[C@]1([H])CCC3C=C(O)C(OC)=CC=3[C@@]1([H])CC2)O |&1:1,2,5,7,20,r|
- CAS DataBase Reference
- 362 · 362-07-2(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- 2 · 2-methoxyestradiol
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- KG7537500
- ridadr
- UN 3077 9/PG 3
- hs_code
- 2937.23.5050
- risk_code
- 23/24/25-36/37/38-48-61-60-46-45-51/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08,GHS09
- hazard_code
- T,Xi,N
- safety_code
- 22-26-36/37/39-45-53-36-61
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H301+H311+H331-H315-H319-H335-H350-H360-H372-H410
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BEye Irrit. 2Repr. 1BSkin Irrit. 2STOT RE 1STOT SE 3
- Precautionary statements
- P273-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
Chemistry & industry
Applications
UsesA natural metabolite of 17Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. Binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule a
UsesA natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. Binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly
Uses2-Methoxyestradiol is a tubulin polymerization inhibitor and also decreases HIF-1 activity.
Uses2-Methoxyestradiol depolymerizes microtubules and blocks HIF-1α nuclear accumulation and HIF-transcriptional activity. Phase 2.
Uses2-Methoxy 17β-Estradiol is a natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. 2-Methoxy 17β-Estradiol binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly and function.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.
Related reactions
1 records
Compound notes
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