(S)-5-{3-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-phenyl}-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol

ID: ALA1083805

PubChem CID: 44596894

Max Phase: Preclinical

Molecular Formula: C30H32N2O5

Molecular Weight: 500.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(CCOc2cccc([C@@H]3Oc4cc(O)ccc4C4=C3c3ccc(O)cc3OCC4)c2)CC1

Standard InChI:  InChI=1S/C30H32N2O5/c1-31-10-12-32(13-11-31)14-16-35-23-4-2-3-20(17-23)30-29-25(24-7-5-22(34)19-28(24)37-30)9-15-36-27-18-21(33)6-8-26(27)29/h2-8,17-19,30,33-34H,9-16H2,1H3/t30-/m0/s1

Standard InChI Key:  YOSGIAVXRSUEKW-PMERELPUSA-N

Molfile:  

     RDKit          2D

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    5.8175    0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5308   -0.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5290    1.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427    0.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2462    0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9636   -0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6824    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2005    2.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9568    1.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8290    2.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6919    2.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4591    1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0643    0.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1320    1.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3944   -1.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1074   -1.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8202   -1.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8157   -0.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1023    0.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1044   -0.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5262    0.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2414   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9519    0.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6671   -0.3513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6674   -1.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3785   -1.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0913   -1.1683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0886   -0.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3730    0.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8050   -1.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 17 18  1  0
  8 10  1  0
 18 19  2  0
 19 14  1  0
  5  4  2  0
 18 20  1  0
  4  1  1  0
  8 21  1  6
  5  6  1  0
 21 22  2  0
 22 23  1  0
  2  3  1  0
 23 24  2  0
 14  9  1  0
 24 25  1  0
 15 10  1  0
 25 26  2  0
 26 21  1  0
 11 12  1  0
  2 27  1  0
 12 13  1  0
 25 28  1  0
 13  9  1  0
 28 29  1  0
 10 11  2  0
 29 30  1  0
  3  6  2  0
 30 31  1  0
 31 32  1  0
  1  2  2  0
 14 15  2  0
  5 11  1  0
 15 16  1  0
  6  7  1  0
 31 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 16 17  2  0
 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083805

   (19S)-19-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8,18-dioxatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2(7),3,5,12(17),13,15-heptaene-5,15-diol

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: 500.60

Molecular Weight (Monoisotopic): 500.2311

AlogP: 4.55

#Rotatable Bonds: 5

Polar Surface Area: 74.63

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.66

CX Basic pKa: 7.78

CX LogP: 3.92

CX LogD: 3.64

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.53

Np Likeness Score: -0.05

References

1. Jain N, Xu J, Kanojia RM, Du F, Jian-Zhong G, Pacia E, Lai MT, Musto A, Allan G, Reuman M, Li X, Hahn D, Cousineau M, Peng S, Ritchie D, Russell R, Lundeen S, Sui Z..  (2009)  Identification and structure-activity relationships of chromene-derived selective estrogen receptor modulators for treatment of postmenopausal symptoms.,  52  (23): [PMID:19366247] [10.1021/jm900146e]

Source

Source(1):

• Scientific Literature