(3aS,5aR,10bS)-3a,10b-dimethyl-1,2,3,3a,7,10b-hexahydroisobenzofuro[7,1-fg]isochromene-4,9(3a1H,5aH)-dione

ID: ALA1092152

PubChem CID: 46881219

Max Phase: Preclinical

Molecular Formula: C16H18O4

Molecular Weight: 274.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12CCC[C@]3(C)C4=CC(=O)OCC4=C[C@@H](OC1=O)C23

Standard InChI:  InChI=1S/C16H18O4/c1-15-4-3-5-16(2)13(15)11(20-14(16)18)6-9-8-19-12(17)7-10(9)15/h6-7,11,13H,3-5,8H2,1-2H3/t11-,13?,15-,16+/m1/s1

Standard InChI Key:  CADKOFRWMORBOD-BPZRQAJTSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
    9.1229  -10.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1229  -11.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8349  -12.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8349  -10.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5470  -10.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5480  -11.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2591  -12.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2569  -10.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6882  -10.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6953   -9.5578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9801   -9.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2578   -9.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0875  -12.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9125  -12.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6017  -13.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9722  -10.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9753  -11.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9857   -8.3143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167  -12.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417   -9.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6667  -12.7375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  8 12  2  0
 16  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 14  1  0
  1  2  1  0
  1  4  1  0
 14  7  1  0
  3 13  1  0
  5  8  1  0
 13 15  2  0
 17 16  2  0
  6  7  1  0
  7 17  1  0
  8 16  1  0
 11 18  2  0
  2  3  1  0
  3 19  1  6
  3  6  1  0
  5 20  1  1
  5  4  1  0
  7 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1092152

   (1S,9R,12S)-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,7-diene-4,11-dione

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 274.32

Molecular Weight (Monoisotopic): 274.1205

AlogP: 2.15

#Rotatable Bonds: ┄

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.12

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: 3.30

References

1. Herath HM, Herath WH, Carvalho P, Khan SI, Tekwani BL, Duke SO, Tomaso-Peterson M, Nanayakkara NP..  (2009)  Biologically active tetranorditerpenoids from the fungus Sclerotinia homoeocarpa causal agent of dollar spot in turfgrass.,  72  (12): [PMID:19928902] [10.1021/np900334k]

Source

Source(1):

• Scientific Literature