(3aS,5R,6S,7aR)-6-hydroxy-5-(2-hydroxy-2-methylpropyl)-6-(4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-enyl)-3a,7a-dimethylhexahydro-1H-inden-4(2H)-one

ID: ALA574264

PubChem CID: 25156144

Max Phase: Preclinical

Molecular Formula: C28H42O5

Molecular Weight: 458.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)c(O)c(C/C=C(\C)C[C@]2(O)C[C@@]3(C)CCC[C@]3(C)C(=O)[C@@H]2CC(C)(C)O)c1

Standard InChI:  InChI=1S/C28H42O5/c1-18(9-10-20-14-21(33-7)13-19(2)23(20)29)15-28(32)17-26(5)11-8-12-27(26,6)24(30)22(28)16-25(3,4)31/h9,13-14,22,29,31-32H,8,10-12,15-17H2,1-7H3/b18-9+/t22-,26+,27+,28-/m0/s1

Standard InChI Key:  WACUKVKVDBBXHA-VCJLGCGKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    5.0986   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0974   -1.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5287   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5258   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8104    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8120   -2.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -2.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    0.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8080    0.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387    0.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9547   -0.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6677    0.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3837   -0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6645    0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0966    0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8125   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8086    1.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0915    0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8083    2.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3759    1.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3737    2.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3667    2.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7833    2.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9542    2.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5244    0.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5196    0.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3005   -0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7880    0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3083    1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5167    1.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5125   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  7  8  1  0
  1  9  1  0
 16 19  1  0
 17 27  1  0
 26 18  1  0
 18 19  1  0
  4  5  1  0
 18 20  2  0
  6 10  1  0
 19 21  1  1
  2  3  1  0
 21 22  1  0
  5 11  1  0
 22 23  1  0
  5  6  2  0
 22 24  1  0
 11 12  1  0
 22 25  1  0
 26 27  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  3  7  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 13 15  1  0
 26 31  1  6
  3  4  2  0
 27 32  1  1
 14 16  1  0
 16 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA574264

   (3aS,5R,6S,7aR)-6-hydroxy-6-[(E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-enyl]-5-(2-hydroxy-2-methylpropyl)-3a,7a-dimethyl-2,3,5,7-tetrahydro-1H-inden-4-one

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: 458.64

Molecular Weight (Monoisotopic): 458.3032

AlogP: 5.27

#Rotatable Bonds: 7

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.11

CX Basic pKa: ┄

CX LogP: 5.38

CX LogD: 5.38

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: 2.10

References

1. Mokrini R, Mesaoud MB, Daoudi M, Hellio C, Maréchal JP, El Hattab M, Ortalo-Magné A, Piovetti L, Culioli G..  (2008)  Meroditerpenoids and derivatives from the brown alga Cystoseira baccata and their antifouling properties.,  71  (11): [PMID:18980381] [10.1021/np8004216]

Source

Source(1):

• Scientific Literature