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

ID: ALA242428

Chembl Id: CHEMBL242428

PubChem CID: 10019418

Max Phase: Preclinical

Molecular Formula: C22H32O2

Molecular Weight: 328.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-N-Butylestradiol | CHEMBL242428|2-n-butylestradiol|BDBM50369005

Canonical SMILES:  CCCCc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12

Standard InChI:  InChI=1S/C22H32O2/c1-3-4-5-15-12-18-14(13-20(15)23)6-7-17-16(18)10-11-22(2)19(17)8-9-21(22)24/h12-13,16-17,19,21,23-24H,3-11H2,1-2H3/t16-,17+,19-,21-,22-/m0/s1

Standard InChI Key:  ZWOYTFHYZDNSHZ-KOLYYURTSA-N

Alternative Forms

1. Parent:

   

   ALA242428

   2-n-Butylestradiol

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: 328.50

Molecular Weight (Monoisotopic): 328.2402

AlogP: 4.95

#Rotatable Bonds: 3

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: 10.59

CX Basic pKa: ┄

CX LogP: 5.59

CX LogD: 5.59

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: 2.00

References

1. 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]

2. 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]

Source

Source(1):

• Scientific Literature