aR-6,7-Dihydro-6-(10-hydroxyethyl)-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,3,9,10,11-hexaol

ID: ALA1089510

PubChem CID: 46866296

Max Phase: Preclinical

Molecular Formula: C18H20O7

Molecular Weight: 348.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(O)C1(C)Cc2cc(O)c(O)c(O)c2-c2c(cc(O)c(O)c2O)C1

Standard InChI:  InChI=1S/C18H20O7/c1-7(19)18(2)5-8-3-10(20)14(22)16(24)12(8)13-9(6-18)4-11(21)15(23)17(13)25/h3-4,7,19-25H,5-6H2,1-2H3

Standard InChI Key:  BOXWNEZQGRBMFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.9111   -7.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099   -7.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247   -8.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3412   -7.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3383   -7.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229   -6.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264   -9.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102   -9.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9097  -10.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246  -10.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415  -10.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3385   -9.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6205   -5.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1965   -6.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951   -8.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -9.2196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1949  -10.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255  -11.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583   -8.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -9.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3417   -8.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9250   -8.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7226   -8.3565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7086   -7.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9250   -9.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  1  0
  6  1  1  0
  6 13  1  0
  1  2  2  0
  1 14  1  0
  3  4  2  0
  2 15  1  0
  7  8  2  0
  8 16  1  0
  9 17  1  0
  8  9  1  0
 10 18  1  0
  4  5  1  0
  4 19  1  0
  9 10  2  0
 12 20  1  0
  2  3  1  0
 19 21  1  0
 20 21  1  0
 10 11  1  0
 21 22  1  0
  5  6  2  0
 22 23  1  0
 11 12  2  0
 22 24  1  0
 12  7  1  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089510

   9-(1-Hydroxyethyl)-9-methyltricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaene-3,4,5,13,14,15-hexol

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: 348.35

Molecular Weight (Monoisotopic): 348.1209

AlogP: 2.07

#Rotatable Bonds: 1

Polar Surface Area: 141.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.14

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.46

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.39

Np Likeness Score: 1.21

References

1. Blunder M, Pferschy-Wenzig EM, Fabian WM, Hüfner A, Kunert O, Saf R, Schühly W, Bauer R..  (2010)  Derivatives of schisandrin with increased inhibitory potential on prostaglandin E(2) and leukotriene B(4) formation in vitro.,  18  (7): [PMID:20236826] [10.1016/j.bmc.2009.10.031]

Source

Source(1):

• Scientific Literature