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

ID: ALA1076991

PubChem CID: 44613658

Max Phase: Preclinical

Molecular Formula: C16H16O5

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16O5/c1-14-4-3-5-15(2)11(14)10(20-13(15)18)12-16(21-12)7-19-9(17)6-8(14)16/h3-4,6,10-12H,5,7H2,1-2H3/t10-,11?,12+,14+,15-,16-/m0/s1

Standard InChI Key:  SSBCRFWUKNDCSZ-ANZWRPDSSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
    3.0857    0.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857   -0.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977   -0.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    0.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -0.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6584    1.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9431    2.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208    1.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504   -1.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8754   -1.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5645   -1.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9352    0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383   -0.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6447    0.2795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487    3.1651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046    1.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506   -0.9251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297   -1.2584    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  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
M  END

Alternative Forms

1. Parent:

   

   ALA1076991

   (1S,2R,4R,10S,14S)-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: 288.30

Molecular Weight (Monoisotopic): 288.0998

AlogP: 1.13

#Rotatable Bonds: ┄

Polar Surface Area: 65.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.40

CX LogD: 1.40

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.38

Np Likeness Score: 4.02

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