Ugonstilbene C; (R,E)-5-(4-Hydroxy-3-((2,6,6-trimethylcyclohex-2-en-1-yl)-methyl)styryl)benzene-1,3-diol

ID: ALA5272060

Max Phase: Preclinical

Molecular Formula: C24H28O3

Molecular Weight: 364.49

Names and Identifiers

Canonical SMILES:  CC1=CCCC(C)(C)[C@H]1Cc1cc(/C=C/c2cc(O)cc(O)c2)ccc1O

Standard InChI:  InChI=1S/C24H28O3/c1-16-5-4-10-24(2,3)22(16)14-19-11-17(8-9-23(19)27)6-7-18-12-20(25)15-21(26)13-18/h5-9,11-13,15,22,25-27H,4,10,14H2,1-3H3/b7-6+/t22-/m0/s1

Standard InChI Key:  MEWJXXAKBKFVOS-WMWRJIBUSA-N

Molfile:  

 
     RDKit          2D

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   -2.1417   -0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399   -2.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563   -1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399   -3.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435   -0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4317   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    0.6173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    1.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    1.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    2.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563    3.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5710    2.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5710    1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563    1.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270    3.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4437    0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4252    0.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  5  7  1  0
  1  8  1  0
  3  9  1  0
  9 10  2  0
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 12 11  2  0
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 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 14 17  1  0
 13 18  1  0
 19 18  1  1
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 19 24  1  0
 20 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5272060

   ---

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: 5.90

#Rotatable Bonds: 4

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.56

CX Basic pKa: ┄

CX LogP: 6.43

CX LogD: 6.40

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: 1.85

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