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

ID: ALA1094047

PubChem CID: 44613789

Max Phase: Preclinical

Molecular Formula: C16H18O5

Molecular Weight: 290.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12C[C@@H](O)C[C@]3(C)C4=CC(=O)OCC4=C[C@@H](OC1=O)C23

Standard InChI:  InChI=1S/C16H18O5/c1-15-5-9(17)6-16(2)13(15)11(21-14(16)19)3-8-7-20-12(18)4-10(8)15/h3-4,9,11,13,17H,5-7H2,1-2H3/t9-,11+,13?,15+,16-/m0/s1

Standard InChI Key:  NQUNKSRIHYKOIX-BWAHQPFKSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -4.9109  -10.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109  -11.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988  -11.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988  -10.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4867  -10.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856  -11.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746  -11.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767  -10.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452  -10.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3381   -9.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0534   -9.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7759   -9.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9463  -12.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1212  -12.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4321  -13.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614  -10.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582  -11.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0478   -8.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9172  -12.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4920   -9.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669  -12.6595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6266  -10.3022    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
  1 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1094047

   (1S,9R,12S,14S)-14-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: 0.73

CX LogD: 0.73

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: 3.37

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]

2. Ren X, Xie X, Chen B, Liu L, Jiang C, Qian Q..  (2021)  Marine Natural Products: A Potential Source of Anti-hepatocellular Carcinoma Drugs.,  64  (12.0): [PMID:34128674] [10.1021/acs.jmedchem.0c02026]

Source

Source(1):

• Scientific Literature