5-((E)-2-((4aR,9aS)-1,1,4a-Trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-7-yl)vinyl)benzene-1,3-diol

ID: ALA5288650

Max Phase: Preclinical

Molecular Formula: C24H28O3

Molecular Weight: 364.49

Names and Identifiers

Canonical SMILES:  CC1(C)CCC[C@@]2(C)Oc3ccc(/C=C/c4cc(O)cc(O)c4)cc3C[C@@H]12

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

Standard InChI Key:  IMDNBZFOPTZQSN-CEQLVMBASA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -2.8567   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -0.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -2.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713   -0.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403   -3.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010   -1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136   -0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    0.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    0.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    0.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    1.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    1.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    0.4655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    2.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565    2.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713    2.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713    1.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    3.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3156    2.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3445    1.9172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2690    0.5763    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
  5  8  1  0
  3  9  1  0
  9 10  2  0
 10 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 13 17  1  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
 14 20  1  0
 18 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 19 24  1  0
 21 25  1  0
 21 26  1  0
 18 27  1  6
 19 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5288650

   ---

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: 8.66

CX Basic pKa: ┄

CX LogP: 6.19

CX LogD: 6.16

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: 1.88

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