(11R,5bS,6R,8aS,10aS,10bR)-6-hydroxy-5b,8a-dimethyl-6,7,8,8a,10a,10b-hexahydro-2H-isobenzofuro[7,1-fg]oxireno[2,3-i]isochromene-4,9(5bH,5b1H)-dione

ID: ALA1096685

PubChem CID: 44613661

Max Phase: Preclinical

Molecular Formula: C16H18O6

Molecular Weight: 306.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12CC[C@@H](O)[C@]3(C)C4=CC(=O)OC[C@]45O[C@@H]5[C@@H](OC1=O)C23

Standard InChI:  InChI=1S/C16H18O6/c1-14-4-3-8(17)15(2)7-5-9(18)20-6-16(7)12(22-16)10(11(14)15)21-13(14)19/h5,8,10-12,17H,3-4,6H2,1-2H3/t8-,10+,11?,12-,14+,15+,16+/m1/s1

Standard InChI Key:  NQJYNKRAHIYEGW-QUGVONPISA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   -4.9146   -4.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146   -5.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2026   -5.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2026   -4.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4905   -4.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895   -5.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784   -5.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -4.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493   -4.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422   -3.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574   -3.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7797   -3.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500   -6.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -6.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358   -7.4418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0653   -4.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622   -5.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3559   -5.1663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0518   -2.2810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9208   -6.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500   -6.3708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -6.7042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2026   -3.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  1  0
 18 17  1  0
 16 18  1  6
  6  7  1  0
  7 17  1  0
  8 16  1  0
  2  3  1  0
 11 19  2  0
  3  6  1  0
  3 20  1  6
  5  4  1  0
  5 21  1  1
  5  6  1  0
 17 22  1  1
  7 23  1  6
  8 12  2  0
  4 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1096685

   (1S,2R,4R,10S,11R,14S)-11-hydroxy-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.02,4.04,9.014,17]heptadec-8-ene-7,15-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: 306.31

Molecular Weight (Monoisotopic): 306.1103

AlogP: 0.33

#Rotatable Bonds: ┄

Polar Surface Area: 85.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.54

CX LogD: 0.54

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: 3.97

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