8-Methoxy-3,3-dimethyl-1-(3-methylbut-2-en-1-yl)-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione

ID: ALA4538037

PubChem CID: 155549076

Max Phase: Preclinical

Molecular Formula: C24H26O5

Molecular Weight: 394.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)C1=CC3CC4C(C)(C)OC(CC=C(C)C)(C3=O)C14O2

Standard InChI:  InChI=1S/C24H26O5/c1-13(2)9-10-23-21(26)14-11-15-20(25)19-16(27-5)7-6-8-17(19)28-24(15,23)18(12-14)22(3,4)29-23/h6-9,11,14,18H,10,12H2,1-5H3

Standard InChI Key:  NCOPXNHFKCYHLL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   15.5837   -8.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5826   -9.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2953   -9.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2935   -8.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0069   -8.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0103   -9.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7275   -9.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7206   -8.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4424   -8.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4434   -9.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1609   -9.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8818   -9.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8808   -8.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1588   -8.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9132   -8.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5655   -8.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3702  -10.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9547  -11.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9520  -11.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8149   -7.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0684   -6.8749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5268   -7.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9360   -7.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5225   -6.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9317   -5.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6998   -6.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7161   -7.2873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2911   -7.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5774   -6.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  1  0
  9 14  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 11 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 13 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
  8 27  2  0
  4 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538037

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.47

Molecular Weight (Monoisotopic): 394.1780

AlogP: 4.06

#Rotatable Bonds: 3

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.96

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: 3.11

References

1. Xu X, Wu Y, Hu M, Li X, Gu C, You Q, Zhang X..  (2016)  Structure-activity relationship of Garcinia xanthones analogues: Potent Hsp90 inhibitors with cytotoxicity and antiangiogenesis activity.,  24  (19): [PMID:27527413] [10.1016/j.bmc.2016.07.067]

Source

Source(1):

• Scientific Literature