(3aS,7aR)-5-(2-hydroxy-2-methylpropyl)-6-(((S)-6-methoxy-2,8-dimethyl-2H-chromen-2-yl)methyl)-3a,7a-dimethyl-3,3a,7,7a-tetrahydro-1H-inden-4(2H)-one

ID: ALA575389

PubChem CID: 25156146

Max Phase: Preclinical

Molecular Formula: C28H38O4

Molecular Weight: 438.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)c2c(c1)C=C[C@](C)(CC1=C(CC(C)(C)O)C(=O)[C@@]3(C)CCC[C@]3(C)C1)O2

Standard InChI:  InChI=1S/C28H38O4/c1-18-13-21(31-7)14-19-9-12-27(5,32-23(18)19)16-20-15-26(4)10-8-11-28(26,6)24(29)22(20)17-25(2,3)30/h9,12-14,30H,8,10-11,15-17H2,1-7H3/t26-,27-,28-/m1/s1

Standard InChI Key:  RHDGWMARJHUFRF-JCYYIGJDSA-N

Molfile:  

     RDKit          2D

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    9.5140   -7.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9391   -5.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9388   -4.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5063   -5.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5040   -4.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4970   -3.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9137   -3.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7934   -5.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0813   -5.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0836   -7.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3671   -6.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3641   -5.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6535   -5.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9415   -5.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445   -6.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6595   -7.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5095   -6.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6636   -7.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2259   -5.4253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240   -4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  6  8  1  0
 13 18  1  6
 14 19  1  1
  1 20  1  0
  8  9  1  0
  2  3  1  0
  9 10  1  0
  1 22  1  0
 20 21  2  0
 21 24  1  0
 23 22  1  0
 23 24  1  0
  3  6  2  0
  9 11  1  0
  4 14  1  0
  9 12  1  0
 13 14  1  0
 13  5  1  0
 23 28  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
  5  6  1  0
  1 29  1  1
  3  4  1  0
 28 30  1  0
  5  7  2  0
 26 31  1  0
  1  2  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA575389

   (3aS,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[[(2S)-6-methoxy-2,8-dimethylchromen-2-yl]methyl]-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

Molecule Features

Natural Product: Yes

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: 438.61

Molecular Weight (Monoisotopic): 438.2770

AlogP: 6.18

#Rotatable Bonds: 5

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.90

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: 2.27

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