(S,E)-5-(4-Hydroxystyryl)-2-((2,6,6-trimethylcyclohex-2-en-1-yl)methyl)benzene-1,3-diol

ID: ALA5282404

Max Phase: Preclinical

Molecular Formula: C24H28O3

Molecular Weight: 364.49

Names and Identifiers

Canonical SMILES:  CC1=CCCC(C)(C)[C@@H]1Cc1c(O)cc(/C=C/c2ccc(O)cc2)cc1O

Standard InChI:  InChI=1S/C24H28O3/c1-16-5-4-12-24(2,3)21(16)15-20-22(26)13-18(14-23(20)27)7-6-17-8-10-19(25)11-9-17/h5-11,13-14,21,25-27H,4,12,15H2,1-3H3/b7-6+/t21-/m1/s1

Standard InChI Key:  PFXULLDGLDNOOD-IRUYWQDXSA-N

Molfile:  

 
     RDKit          2D

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   -1.0657    1.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537    1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537    0.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    1.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0753    1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903    2.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031    2.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180    2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2195    1.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5077    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9327    2.6825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5035   -1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932   -1.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8018   -2.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5207   -2.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2311   -2.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2224   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327   -1.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713   -0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984   -1.6744    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
  1  7  1  0
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  3  9  1  0
  9 10  2  0
 10 11  1  0
 12 11  2  0
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 14 17  1  0
  6 18  1  0
 19 18  1  1
 20 19  1  0
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 22 21  1  0
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 24 23  2  0
 19 24  1  0
 24 25  1  0
 20 26  1  0
 20 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282404

   ---

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: 8.67

CX Basic pKa: ┄

CX LogP: 6.43

CX LogD: 6.41

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: 1.77

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