(4aR,9aS)-6-((E)-4-Hydroxystyryl)-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexa-hydro-1H-xanthen-8-ol

ID: ALA5281744

Max Phase: Preclinical

Molecular Formula: C24H28O3

Molecular Weight: 364.49

Names and Identifiers

Canonical SMILES:  CC1(C)CCC[C@@]2(C)Oc3cc(/C=C/c4ccc(O)cc4)cc(O)c3C[C@@H]12

Standard InChI:  InChI=1S/C24H28O3/c1-23(2)11-4-12-24(3)22(23)15-19-20(26)13-17(14-21(19)27-24)6-5-16-7-9-18(25)10-8-16/h5-10,13-14,22,25-26H,4,11-12,15H2,1-3H3/b6-5+/t22-,24+/m0/s1

Standard InChI Key:  NVDNWXIJCXLGEI-CEQLVMBASA-N

Molfile:  

 
     RDKit          2D

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   -4.2859    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714    0.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -0.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -0.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155    0.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -0.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1596   -1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570    1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -1.3310    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104   -1.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563    1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    0.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859    1.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  8 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
  5 15  1  0
  5 16  1  0
  3 17  1  6
  4 18  1  6
 14 19  1  0
 12 20  1  0
 20 21  2  0
 21 22  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281744

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.49

Molecular Weight (Monoisotopic): 364.2038

AlogP: 5.79

#Rotatable Bonds: 2

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.78

CX Basic pKa: ┄

CX LogP: 6.19

CX LogD: 6.17

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: 2.03

References

1. Lin CT, Yang YH, Cheng JJ, Don MJ..  (2023)  Total Syntheses, Absolute Configurations, and Cytotoxicity Evaluation of Ugonstilbenes A, B, and C from the Rhizomes of Helminthostachys zeylanica.,  86  (2.0): [PMID:36691388] [10.1021/acs.jnatprod.2c00919]

Source

Source(1):

• Scientific Literature