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

ID: ALA1096686

PubChem CID: 44613662

Max Phase: Preclinical

Molecular Formula: C16H16O5

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16O5/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/h3-6,10-11,13,17H,7H2,1-2H3/t10-,11+,13?,15-,16+/m1/s1

Standard InChI Key:  HBGYEPXELMLLBL-QSGGJWILSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    2.5437   -4.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437   -5.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2558   -6.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2558   -4.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9678   -4.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9688   -5.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6799   -6.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -4.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091   -4.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1161   -3.6828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009   -3.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786   -3.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -6.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333   -6.9334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -7.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3930   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3962   -5.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065   -2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299   -6.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -6.8625    0.0000 H   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  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
  2 20  1  1
  5  4  1  0
  5 21  1  1
  5  6  1  0
  7 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1096686

   (1S,9R,12R,13S)-13-hydroxy-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: 288.30

Molecular Weight (Monoisotopic): 288.0998

AlogP: 0.89

#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: 0.68

CX LogD: 0.68

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: 3.72

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