CHEBI:28955 - 2-methoxy-17β-estradiol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 2-methoxy-17β-estradiol
ChEBI ID CHEBI:28955
ChEBI ASCII Name 2-methoxy-17beta-estradiol
Definition A 17β-hydroxy steroid, being 17β-estradiol methoxylated at C-2.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42274, CHEBI:19675, CHEBI:1187
Supplier Information ChemicalBook:CB5268052, eMolecules:486062, eMolecules:30487811, Selleckchem:2-Methoxyestradiol(2ME2), ZINC000003818826
Download Molfile XML SDF
Formula C19H26O3
Net Charge 0
Average Mass 302.40794
Monoisotopic Mass 302.18819
InChI InChI=1S/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-/m0/s1
InChIKey CQOQDQWUFQDJMK-SSTWWWIQSA-N
SMILES [H][C@]12CC[C@]3(C)[C@@H](O)CC[C@@]3([H])[C@]1([H])CCc1cc(O)c(OC)cc21
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
antimitotic
Any compound that inhibits cell division (mitosis).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): angiogenesis modulating agent
An agent that modulates the physiologic angiogenesis process. This is accomplished by endogenous angiogenic proteins and a variety of other chemicals and pharmaceutical agents.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 2-methoxy-17β-estradiol (CHEBI:28955) has functional parent 17β-estradiol (CHEBI:16469)
2-methoxy-17β-estradiol (CHEBI:28955) has role angiogenesis modulating agent (CHEBI:50926)
2-methoxy-17β-estradiol (CHEBI:28955) has role antimitotic (CHEBI:64911)
2-methoxy-17β-estradiol (CHEBI:28955) has role antineoplastic agent (CHEBI:35610)
2-methoxy-17β-estradiol (CHEBI:28955) has role human metabolite (CHEBI:77746)
2-methoxy-17β-estradiol (CHEBI:28955) has role metabolite (CHEBI:25212)
2-methoxy-17β-estradiol (CHEBI:28955) has role mouse metabolite (CHEBI:75771)
2-methoxy-17β-estradiol (CHEBI:28955) is a 17β-hydroxy steroid (CHEBI:35343)
2-methoxy-17β-estradiol (CHEBI:28955) is a 3-hydroxy steroid (CHEBI:36834)
Incoming 2-methoxy-17β-estradiol 3-O-(β-D-glucuronide) (CHEBI:36491) has functional parent 2-methoxy-17β-estradiol (CHEBI:28955)
IUPAC Name
2-methoxyestra-1,3,5(10)-triene-3,17β-diol
Synonyms Sources
1,3,5(10)-ESTRATRIEN-2,3,17-BETA-TRIOL 2-METHYL ETHER PDBeChem
2-Hydroxyestradol 2-methyl ether ChemIDplus
2-methoxy-17β-estradiol UniProt
2-methoxyestradiol ChEBI
2-Methoxyestradiol-17beta KEGG COMPOUND
Panzem ChemIDplus
Manual Xrefs Databases
C05302 KEGG COMPOUND
CA2499254 Patent
CN1672746 Patent
JP2005270658 Patent
LMST02010035 LIPID MAPS
US2009104246 Patent
View more database links
Registry Numbers Types Sources
3147966 Reaxys Registry Number Reaxys
362-07-2 CAS Registry Number KEGG COMPOUND
362-07-2 CAS Registry Number ChemIDplus
Citations
Kulke MH, Chan JA, Meyerhardt JA, Zhu AX, Abrams TA, Blaszkowsky LS, Regan E, Sidor C, Fuchs CS (2011)
A prospective phase II study of 2-methoxyestradiol administered in combination with bevacizumab in patients with metastatic carcinoid tumors.
Cancer chemotherapy and pharmacology 68, 293-300 [PubMed:20960192]
[show Abstract]
Harrison MR, Hahn NM, Pili R, Oh WK, Hammers H, Sweeney C, Kim K, Perlman S, Arnott J, Sidor C, Wilding G, Liu G (2011)
A phase II study of 2-methoxyestradiol (2ME2) NanoCrystal® dispersion (NCD) in patients with taxane-refractory, metastatic castrate-resistant prostate cancer (CRPC).
Investigational new drugs 29, 1465-1474 [PubMed:20499131]
[show Abstract]
Tevaarwerk AJ, Holen KD, Alberti DB, Sidor C, Arnott J, Quon C, Wilding G, Liu G (2009)
Phase I trial of 2-methoxyestradiol NanoCrystal dispersion in advanced solid malignancies.
Clinical cancer research : an official journal of the American Association for Cancer Research 15, 1460-1465 [PubMed:19228747]
[show Abstract]
Matei D, Schilder J, Sutton G, Perkins S, Breen T, Quon C, Sidor C (2009)
Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial.
Gynecologic oncology 115, 90-96 [PubMed:19577796]
[show Abstract]
LaVallee TM, Burke PA, Swartz GM, Hamel E, Agoston GE, Shah J, Suwandi L, Hanson AD, Fogler WE, Sidor CF, Treston AM (2008)
Significant antitumor activity in vivo following treatment with the microtubule agent ENMD-1198.
Molecular cancer therapeutics 7, 1472-1482 [PubMed:18566218]
[show Abstract]
James J, Murry DJ, Treston AM, Storniolo AM, Sledge GW, Sidor C, Miller KD (2007)
Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer.
Investigational new drugs 25, 41-48 [PubMed:16969706]
[show Abstract]
Funakoshi T, Birsner AE, D'Amato RJ (2006)
Antiangiogenic effect of oral 2-methoxyestradiol on choroidal neovascularization in mice.
Experimental eye research 83, 1102-1107 [PubMed:16828472]
[show Abstract]
LaVallee TM, Zhan XH, Johnson MS, Herbstritt CJ, Swartz G, Williams MS, Hembrough WA, Green SJ, Pribluda VS (2003)
2-methoxyestradiol up-regulates death receptor 5 and induces apoptosis through activation of the extrinsic pathway.
Cancer research 63, 468-475 [PubMed:12543804]
[show Abstract]
Lottering ML, de Kock M, Viljoen TC, Grobler CJ, Seegers JC (1996)
17beta-Estradiol metabolites affect some regulators of the MCF-7 cell cycle.
Cancer letters 110, 181-186 [PubMed:9018099]
[show Abstract]
Last Modified
05 May 2017