(4aS,6aR,12aR,12bS)-10-allyloxy-4,4,6a,12b-tetramethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthene

ID: ALA5208112

PubChem CID: 168294962

Max Phase: Preclinical

Molecular Formula: C24H34O2

Molecular Weight: 354.53

Names and Identifiers

Canonical SMILES:  C=CCOc1ccc2c(c1)C[C@@H]1[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]1(C)O2

Standard InChI:  InChI=1S/C24H34O2/c1-6-14-25-18-8-9-19-17(15-18)16-21-23(4)12-7-11-22(2,3)20(23)10-13-24(21,5)26-19/h6,8-9,15,20-21H,1,7,10-14,16H2,2-5H3/t20-,21+,23-,24+/m0/s1

Standard InChI Key:  AGENWNRBIWJBGS-SGKWCMOWSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    0.7099    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362    0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -0.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099   -0.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -1.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -1.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015   -0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7241   -2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0126   -2.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -1.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4151   -2.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1362   -1.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -1.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281   -3.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -3.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -3.3564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -0.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    2.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    2.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335   -2.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    3.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036    3.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892   -2.1115    0.0000 H   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
  8  7  1  0
  9  8  1  0
 10  9  1  0
  6 10  1  0
  8 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  9 14  1  0
 13 15  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 14 18  1  0
 15 19  1  0
 15 20  1  0
 13 21  1  6
 14 22  1  1
  2 23  1  0
 23 24  1  0
  8 25  1  1
 24 26  1  0
 26 27  2  0
  9 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5208112

   ---

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: 354.53

Molecular Weight (Monoisotopic): 354.2559

AlogP: 6.19

#Rotatable Bonds: 3

Polar Surface Area: 18.46

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.33

CX LogD: 6.33

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: 1.94

References

1. Wang X, Hu N, Kong W, Song B, Li S..  (2022)  Facile and divergent optimization of chromazonarol enabled the identification of simplified drimane meroterpenoids as novel pharmaceutical leads.,  227  [PMID:34653771] [10.1016/j.ejmech.2021.113912]

Source

Source(1):

• Scientific Literature