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

ID: ALA1094046

PubChem CID: 44613788

Max Phase: Preclinical

Molecular Formula: C16H18O5

Molecular Weight: 290.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H18O5/c1-15-4-3-11(17)16(2)13(15)10(21-14(16)19)5-8-7-20-12(18)6-9(8)15/h5-6,10-11,13,17H,3-4,7H2,1-2H3/t10-,11-,13?,15-,16+/m1/s1

Standard InChI Key:  FLYQLHNNCNPTGV-LCLYFNTLSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   14.6021   -4.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6021   -5.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3141   -6.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3141   -4.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0261   -4.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0272   -5.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7382   -6.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7361   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1674   -4.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1745   -3.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4593   -3.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7369   -3.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5666   -6.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3916   -6.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0808   -7.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4513   -4.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4545   -5.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4649   -2.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5958   -6.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0208   -4.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1458   -6.8500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8882   -6.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  5  6  1  0
  2 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1094046

   (1S,9R,12R,13R)-13-hydroxy-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: 290.31

Molecular Weight (Monoisotopic): 290.1154

AlogP: 1.12

#Rotatable Bonds: ┄

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.89

CX LogD: 0.89

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: 3.65

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