(3aR,4S,9R,9aR)-6,7-bis(benzyloxy)-1-oxo-9-(3,4,5-trimethoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho[2,3-c]furan-4-yl 3-nitrobenzoate

ID: ALA2288955

PubChem CID: 76334737

Max Phase: Preclinical

Molecular Formula: C42H37NO11

Molecular Weight: 731.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc(OCc4ccccc4)c(OCc4ccccc4)cc3[C@@H](OC(=O)c3cccc([N+](=O)[O-])c3)[C@H]3COC(=O)[C@H]23)cc(OC)c1OC

Standard InChI:  InChI=1S/C42H37NO11/c1-48-35-18-28(19-36(49-2)40(35)50-3)37-30-20-33(51-22-25-11-6-4-7-12-25)34(52-23-26-13-8-5-9-14-26)21-31(30)39(32-24-53-42(45)38(32)37)54-41(44)27-15-10-16-29(17-27)43(46)47/h4-21,32,37-39H,22-24H2,1-3H3/t32-,37+,38-,39+/m0/s1

Standard InChI Key:  UBBNRNVRCCQRIH-PJOJJWDTSA-N

Molfile:  

     RDKit          2D

 54 60  0  0  0  0  0  0  0  0999 V2000
   34.5983   -6.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5965   -5.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3051   -5.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3039   -6.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0140   -6.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0164   -5.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7310   -5.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7278   -6.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5098   -6.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9964   -5.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5151   -5.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8902   -6.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8915   -5.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1150   -5.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1136   -6.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0164   -4.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0130   -7.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3057   -7.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3044   -8.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0121   -9.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7227   -8.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7205   -7.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7592   -7.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5960   -9.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8889   -8.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0122   -9.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3046  -10.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4313   -9.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4332   -9.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1126   -4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0749   -7.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7242   -3.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7242   -2.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4319   -4.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4313   -2.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4316   -1.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7234   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0133   -1.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0164   -2.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1397   -1.3619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1401   -0.5447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8472   -1.7709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4037   -3.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3486   -7.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4062   -3.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6982   -2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9907   -3.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9957   -3.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7043   -4.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6653   -7.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9396   -7.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9004   -8.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5930   -8.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3159   -8.5305    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  1
  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  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 33  1  0
 40 41  2  0
 40 42  1  0
 36 40  1  0
 30 43  1  0
 31 44  1  0
 43 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 49 43  1  0
 44 50  2  0
 50 51  1  0
 51 52  2  0
 52 53  1  0
 53 54  2  0
 54 44  1  0
M  CHG  2  40   1  42  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288955

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

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: 731.75

Molecular Weight (Monoisotopic): 731.2367

AlogP: 7.61

#Rotatable Bonds: 13

Polar Surface Area: 141.89

Molecular Species: NEUTRAL

HBA: 11

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.57

CX LogD: 7.57

Aromatic Rings: 5

Heavy Atoms: 54

QED Weighted: 0.07

Np Likeness Score: 0.45

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