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

ID: ALA1077016

PubChem CID: 44613787

Max Phase: Preclinical

Molecular Formula: C16H16O4

Molecular Weight: 272.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12C=CC[C@]3(C)C(=O)O[C@H](C=C4COC(=O)C=C41)C23

Standard InChI:  InChI=1S/C16H16O4/c1-15-4-3-5-16(2)13(15)11(20-14(16)18)6-9-8-19-12(17)7-10(9)15/h3-4,6-7,11,13H,5,8H2,1-2H3/t11-,13?,15-,16+/m1/s1

Standard InChI Key:  MBIOLILLUPAUBU-BPZRQAJTSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
    8.6354   -4.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6354   -5.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3474   -6.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3474   -4.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0595   -4.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0605   -5.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7716   -6.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7694   -4.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2007   -4.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2078   -3.5453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4926   -3.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7703   -3.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6000   -6.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250   -6.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1142   -7.4627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4847   -4.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4878   -5.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4982   -2.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0542   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1792   -6.7250    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  2  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:

   

   ALA1077016

   (1S,9R,12S)-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,7,14-triene-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: 272.30

Molecular Weight (Monoisotopic): 272.1049

AlogP: 1.92

#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: 1.76

CX LogD: 1.76

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.50

Np Likeness Score: 3.75

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