(3aR,4R,9R,9aR)-6,7-dimethoxy-1-oxo-9-(3,4,5-trimethoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho[2,3-c]furan-4-yl 2-phenylacetate

ID: ALA2288939

PubChem CID: 71541412

Max Phase: Preclinical

Molecular Formula: C31H32O9

Molecular Weight: 548.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)[C@H](OC(=O)Cc1ccccc1)[C@H]1COC(=O)[C@@H]1[C@@H]2c1cc(OC)c(OC)c(OC)c1

Standard InChI:  InChI=1S/C31H32O9/c1-34-22-14-19-20(15-23(22)35-2)29(40-26(32)11-17-9-7-6-8-10-17)21-16-39-31(33)28(21)27(19)18-12-24(36-3)30(38-5)25(13-18)37-4/h6-10,12-15,21,27-29H,11,16H2,1-5H3/t21-,27+,28-,29-/m0/s1

Standard InChI Key:  MNNWQAHBHHWJQT-RUZQMMQPSA-N

Molfile:  

     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
   34.7510   -9.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7492   -7.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4578   -8.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4566   -8.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1667   -9.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1691   -7.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8838   -8.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8805   -8.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6625   -9.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1491   -8.5664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6678   -7.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0429   -8.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0442   -8.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2680   -7.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2660   -9.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1691   -6.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1657  -10.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4584  -10.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4571  -11.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1648  -11.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8754  -11.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8732  -10.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9119  -10.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7487  -11.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0417  -11.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1649  -12.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4573  -13.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5840  -11.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5859  -12.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0993   -7.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0948  -10.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8769   -6.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8769   -5.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5846   -6.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5846   -5.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2878   -5.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9950   -5.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9955   -4.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2828   -4.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5785   -4.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0
  1  4  2  0
  3  2  2  0
  2 13  1  0
  3  4  1  0
  3  6  1  0
  4  5  1  0
  5  8  1  0
  7  6  1  0
  7  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
  7 11  1  1
 12 13  2  0
 13 14  1  0
 15 12  1  0
  6 16  1  6
  5 17  1  6
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  9 23  2  0
 19 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
 21 28  1  0
 28 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288939

   [(3aR,4R,9R,9aR)-6,7-dimethoxy-1-oxo-9-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-3H-benzo[f][2]benzofuran-4-yl] 2-phenylacetate

Molecule Features

Natural Product: No

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: 548.59

Molecular Weight (Monoisotopic): 548.2046

AlogP: 4.49

#Rotatable Bonds: 9

Polar Surface Area: 98.75

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.36

Np Likeness Score: 1.05

References

1. He S, Shao Y, Fan L, Che Z, Xu H, Zhi X, Wang J, Yao X, Qu H..  (2013)  Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents.,  61  (3): [PMID:23278333] [10.1021/jf305011n]

Source

Source(1):

• Scientific Literature