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

ID: ALA575826

PubChem CID: 25155861

Max Phase: Preclinical

Molecular Formula: C28H40O4

Molecular Weight: 440.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)c(O)c(C/C=C(\C)CC2=C(CC(C)(C)O)C(=O)[C@@]3(C)CCC[C@]3(C)C2)c1

Standard InChI:  InChI=1S/C28H40O4/c1-18(9-10-20-15-22(32-7)14-19(2)24(20)29)13-21-16-27(5)11-8-12-28(27,6)25(30)23(21)17-26(3,4)31/h9,14-15,29,31H,8,10-13,16-17H2,1-7H3/b18-9+/t27-,28-/m1/s1

Standard InChI Key:  FFNCYUFWSPYUFV-FIAZMKCYSA-N

Molfile:  

     RDKit          2D

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   -3.5921   -1.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3067   -2.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0202    0.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    1.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654    0.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4041    2.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0305    2.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    3.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1203    1.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9041    1.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125    2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  1  0
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  7  8  1  0
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 16 19  2  0
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 26 18  1  0
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  4  5  1  0
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  2  3  1  0
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  5 11  1  0
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  5  6  2  0
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 11 12  1  0
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  6  1  1  0
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  1  2  2  0
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 13 15  1  0
 26 31  1  6
  3  4  2  0
 27 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA575826

   (3aS,7aR)-6-[(E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-enyl]-5-(2-hydroxy-2-methylpropyl)-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-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: 440.62

Molecular Weight (Monoisotopic): 440.2927

AlogP: 6.22

#Rotatable Bonds: 7

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.11

CX Basic pKa: ┄

CX LogP: 6.34

CX LogD: 6.34

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 2.02

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