(R)-5-[3-(2-Thiomorpholin-4-yl-ethoxy)-phenyl]-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol

ID: ALA1086388

PubChem CID: 44596358

Max Phase: Preclinical

Molecular Formula: C29H29NO5S

Molecular Weight: 503.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc2c(c1)O[C@H](c1cccc(OCCN3CCSCC3)c1)C1=C2CCOc2cc(O)ccc21

Standard InChI:  InChI=1S/C29H29NO5S/c31-20-5-7-25-26(17-20)34-12-8-24-23-6-4-21(32)18-27(23)35-29(28(24)25)19-2-1-3-22(16-19)33-13-9-30-10-14-36-15-11-30/h1-7,16-18,29,31-32H,8-15H2/t29-/m1/s1

Standard InChI Key:  IYLBPELTTFJGJQ-GDLZYMKVSA-N

Molfile:  

     RDKit          2D

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   16.9294   -0.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6422   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6404    0.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3538    0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3572   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0744   -1.1749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7928   -0.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3106    1.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7902    0.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0675    0.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.8017    1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5690    0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1739   -0.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0115   -0.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.5044   -1.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2169   -2.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9294   -1.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9250   -1.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2118   -0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2166   -1.1735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6351   -0.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3500   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0600   -0.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7749   -1.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7751   -1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4858   -2.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1984   -1.9613    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.1956   -1.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4803   -0.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0
  7  8  1  0
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  8 10  1  0
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 19 14  1  0
  5  4  2  0
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  4  1  1  0
  8 21  1  1
  5  6  1  0
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  2  3  1  0
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 14  9  1  0
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA1086388

   (19R)-19-[3-(2-thiomorpholin-4-ylethoxy)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: 503.62

Molecular Weight (Monoisotopic): 503.1766

AlogP: 5.35

#Rotatable Bonds: 5

Polar Surface Area: 71.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.66

CX Basic pKa: 7.77

CX LogP: 4.43

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.49

Np Likeness Score: -0.15

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