17-Ethynyl-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA1628161

Chembl Id: CHEMBL1628161

Cas Number: 34816-55-2

PubChem CID: 11954041

Max Phase: Phase

Molecular Formula: C21H26O3

Molecular Weight: 326.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Metoxiestrol | R 2858 | R-2858 | Moxestrol|34816-55-2|R 2858|11beta-Methoxyethinylestradiol|METOXIESTROL|CHEBI:34857|R-2858|6923NT44OW|17alpha-Ethinyl-11beta-methoxy-1,3,5(10)-estratrien-3,17-diol|Moxestrolum|(8S,9S,11S,13S,14S,17R)-17-ethynyl-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol|Moxestrol [INN:DCF]|Moxestrolum [INN-Latin]|11-beta-Methoxy-17-alpha-ethinylestradiol|UNII-6923NT44OW|CCRIS 7199|RU 2858|BRN 4264994|MOXESTROL [INN]|MOXESTROL Show More⌵

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3[C@@H](OC)C[C@@]21C

Standard InChI:  InChI=1S/C21H26O3/c1-4-21(23)10-9-17-16-7-5-13-11-14(22)6-8-15(13)19(16)18(24-3)12-20(17,21)2/h1,6,8,11,16-19,22-23H,5,7,9-10,12H2,2-3H3/t16-,17-,18-,19+,20-,21-/m0/s1

Standard InChI Key:  MTMZZIPTQITGCY-OLGWUGKESA-N

Alternative Forms

1. Parent:

   

   ALA1628161

   MOXESTROL

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 326.44

Molecular Weight (Monoisotopic): 326.1882

AlogP: 3.24

#Rotatable Bonds: 1

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.21

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 1.80

References

1. VanBrocklin HF, Carlson KE, Katzenellenbogen JA, Welch MJ..  (1993)  16 beta-([18F]fluoro)estrogens: systematic investigation of a new series of fluorine-18-labeled estrogens as potential imaging agents for estrogen-receptor-positive breast tumors.,  36  (11): [PMID:7684451] [10.1021/jm00063a012]

2. Peters RH, Crowe DF, Avery MA, Chong WK, Tanabe M..  (1989)  17-Desoxy estrogen analogues.,  32  (7): [PMID:2738897] [10.1021/jm00127a040]

3. Christiansen LB, Wenckens M, Bury PS, Gissel B, Hansen BS, Thorpe SM, Jacobsen P, Kanstrup A, Jørgensen AS, Naerum L, Wassermann K..  (2002)  Synthesis and biological evaluation of novel thio-substituted chromanes as high-affinity partial agonists for the estrogen receptor.,  12  (1): [PMID:11738564] [10.1016/s0960-894x(01)00679-5]

4. Jørgensen AS, Jacobsen P, Christiansen LB, Bury PS, Kanstrup A, Thorpe SM, Bain S, Naerum L, Wassermann K..  (2000)  Synthesis and pharmacology of a novel pyrrolo[2,1,5-cd] indolizine (NNC 45-0095), a high affinity non-steroidal agonist for the estrogen receptor.,  10  (4): [PMID:10714509] [10.1016/s0960-894x(00)00015-9]

5. Gantchev TG, Ali H, van Lier JE..  (1994)  Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives.,  37  (24): [PMID:7990116] [10.1021/jm00050a013]

6. Napolitano E, Fiaschi R, Carlson KE, Katzenellenbogen JA..  (1995)  11 beta-Substituted estradiol derivatives, potential high-affinity carbon-11-labeled probes for the estrogen receptor: a structure-affinity relationship study.,  38  (3): [PMID:7853335] [10.1021/jm00003a005]

7. Ali H, Rousseau J, Ghaffari MA, van Lier JE..  (1991)  Synthesis, receptor binding, and tissue distribution of 7 alpha- and 11 beta-substituted (17 alpha,20E)- and (17 alpha,20Z)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diols.,  34  (2): [PMID:1995909] [10.1021/jm00106a054]

8. Jolivette LJ, Ward KW..  (2005)  Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.,  94  (7): [PMID:15920768] [10.1002/jps.20373]

9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

10. WHO Anatomical Therapeutic Chemical Classification, 

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification