(3aR,4S,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 3-nitrobenzoate

ID: ALA2288951

PubChem CID: 71541615

Max Phase: Preclinical

Molecular Formula: C30H29NO11

Molecular Weight: 579.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)[C@@H](OC(=O)c1cccc([N+](=O)[O-])c1)[C@H]1COC(=O)[C@@H]1[C@@H]2c1cc(OC)c(OC)c(OC)c1

Standard InChI:  InChI=1S/C30H29NO11/c1-36-21-12-18-19(13-22(21)37-2)27(42-29(32)15-7-6-8-17(9-15)31(34)35)20-14-41-30(33)26(20)25(18)16-10-23(38-3)28(40-5)24(11-16)39-4/h6-13,20,25-27H,14H2,1-5H3/t20-,25+,26-,27+/m0/s1

Standard InChI Key:  BPGSCNOHCGMLIM-ULBKPHCJSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  0  0  0  0  0  0999 V2000
   36.0676  -27.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0658  -26.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7744  -26.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7732  -27.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4833  -27.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4857  -26.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2003  -26.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1971  -27.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9791  -27.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4657  -26.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.9844  -26.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3595  -27.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3607  -26.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5846  -26.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5826  -27.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4857  -25.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4823  -28.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7750  -28.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7737  -29.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4814  -30.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1920  -29.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1898  -28.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2285  -28.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0653  -30.1844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3582  -29.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4815  -31.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7738  -31.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9006  -30.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.9025  -30.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4159  -25.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4114  -28.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1935  -24.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1935  -24.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9011  -25.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.9005  -23.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9009  -22.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1927  -22.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4826  -22.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4857  -23.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6090  -22.4108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6094  -21.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3165  -22.8197    0.0000 O   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
M  CHG  2  40   1  42  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288951

   [(3aR,4S,9R,9aR)-6,7-dimethoxy-1-oxo-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: 579.56

Molecular Weight (Monoisotopic): 579.1741

AlogP: 4.47

#Rotatable Bonds: 9

Polar Surface Area: 141.89

Molecular Species: NEUTRAL

HBA: 11

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: 0.69

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