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

ID: ALA1098372

PubChem CID: 46881201

Max Phase: Preclinical

Molecular Formula: C16H16O6

Molecular Weight: 304.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C=C[C@H](O)[C@]3(C)C(=O)O[C@@H](C13)[C@H]1O[C@]13COC(=O)C=C32

Standard InChI:  InChI=1S/C16H16O6/c1-14-4-3-8(17)15(2)11(14)10(21-13(15)19)12-16(22-12)6-20-9(18)5-7(14)16/h3-5,8,10-12,17H,6H2,1-2H3/t8-,10-,11?,12+,14+,15-,16-/m0/s1

Standard InChI Key:  OAEPKMHZKLINLT-LEYZZPCFSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   -3.4521    0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4521    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401   -0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0280    0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0270    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3159   -0.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    1.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1132    1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203    2.0630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949    2.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172    2.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625   -1.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733   -1.8543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028    0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997    0.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1066    0.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893    3.3065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4583   -0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1660   -0.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333    1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -0.7833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -1.1167    0.0000 H   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  2  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
  2 21  1  1
  5  6  1  0
  5 22  1  1
 17 23  1  1
  8 12  2  0
  7 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1098372

   (1S,2R,4R,10S,13S,14R)-13-hydroxy-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.02,4.04,9.014,17]heptadeca-8,11-diene-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: 304.30

Molecular Weight (Monoisotopic): 304.0947

AlogP: 0.11

#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: 0.33

CX LogD: 0.33

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.39

Np Likeness Score: 3.98

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