(13S,17S)-2,13-Dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA241993

Chembl Id: CHEMBL241993

Cas Number: 1818-12-8

PubChem CID: 66425

Max Phase: Preclinical

Molecular Formula: C19H26O2

Molecular Weight: 286.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Methylestradiol | 2-Methyl estradiol|2-Methylestradiol|1818-12-8|(8R,9S,13S,14S,17S)-2,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol|CHEMBL241993|2-Methyl Estradiol 17-Valerate|NSC666605|SCHEMBL3868013|DTXSID50939472|BDBM50369009|NSC-666605|NCI60_023222|2-Methylestra-1(10),2,4-triene-3,17-diol|Estra-1,3,5(10)-triene-3,17-diol, 2-methyl-, (17beta)-

Canonical SMILES:  Cc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12

Standard InChI:  InChI=1S/C19H26O2/c1-11-9-15-12(10-17(11)20)3-4-14-13(15)7-8-19(2)16(14)5-6-18(19)21/h9-10,13-14,16,18,20-21H,3-8H2,1-2H3/t13-,14+,16-,18-,19-/m0/s1

Standard InChI Key:  PAZNMSHBVDFVSA-NNYOOSKESA-N

Alternative Forms

1. Parent:

   

   ALA241993

   2-Methyl estradiol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 286.42

Molecular Weight (Monoisotopic): 286.1933

AlogP: 3.92

#Rotatable Bonds: ┄

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.66

CX Basic pKa: ┄

CX LogP: 4.26

CX LogD: 4.26

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.76

Np Likeness Score: 2.21

References

1. Wurtz JM, Egner U, Heinrich N, Moras D, Mueller-Fahrnow A..  (1998)  Three-dimensional models of estrogen receptor ligand binding domain complexes, based on related crystal structures and mutational and structure-activity relationship data.,  41  (11): [PMID:9599231] [10.1021/jm970406v]

2. Cushman M, He HM, Katzenellenbogen JA, Lin CM, Hamel E..  (1995)  Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.,  38  (12): [PMID:7783135] [10.1021/jm00012a003]

3. Bubert C, Leese MP, Mahon MF, Ferrandis E, Regis-Lydi S, Kasprzyk PG, Newman SP, Ho YT, Purohit A, Reed MJ, Potter BV..  (2007)  3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.,  50  (18): [PMID:17696419] [10.1021/jm070405v]

4. PubChem BioAssay data set, 

5. Yadav MR, Barmade MA, Tamboli RS, Murumkar PR..  (2015)  Developing steroidal aromatase inhibitors-an effective armament to win the battle against breast cancer.,  105  [PMID:26469743] [10.1016/j.ejmech.2015.09.038]

6. Poirier D, Roy J, Cortés-Benítez F, Dutour R..  (2016)  Targeting cytochrome P450 (CYP) 1B1 with steroid derivatives.,  26  (21): [PMID:27687674] [10.1016/j.bmcl.2016.09.046]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays