5-[4-(3-Hydroxypropoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthal ene-2,8-diol

ID: ALA1084913

PubChem CID: 44597970

Max Phase: Preclinical

Molecular Formula: C26H24O6

Molecular Weight: 432.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCCOc1ccc(C2Oc3cc(O)ccc3C3=C2c2ccc(O)cc2OCC3)cc1

Standard InChI:  InChI=1S/C26H24O6/c27-11-1-12-30-19-6-2-16(3-7-19)26-25-21(20-8-4-18(29)15-24(20)32-26)10-13-31-23-14-17(28)5-9-22(23)25/h2-9,14-15,26-29H,1,10-13H2

Standard InChI Key:  DVEXRUSVKFNKTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -5.1032  -11.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1044  -12.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3916  -12.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3934  -10.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6802  -11.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767  -12.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9597  -12.5624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414  -12.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236   -9.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440  -11.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665  -10.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942  -10.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5452   -9.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325  -10.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651  -11.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604  -11.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228  -11.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067  -10.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -9.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0469  -10.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281  -12.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298  -13.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8173  -13.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1049  -13.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094  -12.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8224  -12.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089  -13.7843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199  -13.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338  -13.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8171  -12.5610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447  -13.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585  -13.7741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  5 11  1  0
 15 16  1  0
  6  7  1  0
 16 17  2  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  0
  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
 24 27  1  0
 12 13  1  0
 27 28  1  0
 13  9  1  0
 28 29  1  0
 10 11  2  0
  2 30  1  0
  3  6  2  0
 29 31  1  0
  1  2  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084913

   19-[4-(3-Hydroxypropoxy)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: 432.47

Molecular Weight (Monoisotopic): 432.1573

AlogP: 4.69

#Rotatable Bonds: 5

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.61

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.72

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: 0.66

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