3-detigloylisoswietemahonin G

ID: ALA2271724

PubChem CID: 76312532

Max Phase: Preclinical

Molecular Formula: C27H34O9

Molecular Weight: 502.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(O)[C@H]1C(C)(C)[C@@H](O)[C@@H]2C(=O)[C@]1(C)[C@H]1CC[C@]3(C)[C@@H](CC(=O)O[C@H]3c3ccoc3)[C@]13O[C@@H]23

Standard InChI:  InChI=1S/C27H34O9/c1-24(2)18(17(29)23(32)33-5)26(4)13-6-8-25(3)14(10-15(28)35-21(25)12-7-9-34-11-12)27(13)22(36-27)16(19(24)30)20(26)31/h7,9,11,13-14,16-19,21-22,29-30H,6,8,10H2,1-5H3/t13-,14-,16-,17?,18+,19+,21+,22+,25-,26-,27-/m1/s1

Standard InChI Key:  VXGKLPCLRJEILZ-LWJYOGFISA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
    9.4821  -17.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1967  -16.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8876  -15.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5651  -18.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8231  -18.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1461  -15.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3485  -13.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1922  -13.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330  -17.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0945  -15.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1273  -14.6904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9634  -16.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8588  -15.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9307  -17.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5986  -14.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4109  -19.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1823  -17.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4438  -14.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3797  -15.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4658  -16.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6223  -15.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6864  -14.1790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5819  -13.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7006  -16.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4285  -12.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6521  -12.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7316  -11.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3821  -10.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0977  -10.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6441  -11.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3411  -19.8577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7276  -16.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2423  -15.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5220  -17.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4665  -16.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2963  -17.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  4  5  1  0
  5 34  1  0
  6  3  1  0
  6 33  1  0
  6  8  1  1
 33 19  1  0
 18  7  1  0
  7  8  1  0
  5  9  1  1
  3  9  1  0
  2 10  1  6
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  3 15  1  6
  1 16  1  0
  1 17  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  1
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 18 25  1  6
 27 28  1  0
 26 27  2  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 23 26  1  6
  4 31  1  6
 13 32  1  0
 34 33  1  0
 34 35  1  1
 33 35  1  6
  9 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271724

   3-DETIGLOYLISOSWIETEMAHONIN G

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: 502.56

Molecular Weight (Monoisotopic): 502.2203

AlogP: 2.19

#Rotatable Bonds: 3

Polar Surface Area: 135.80

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.41

CX Basic pKa: ┄

CX LogP: 1.78

CX LogD: 1.78

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.47

Np Likeness Score: 2.88

References

1. Fowles R, Mootoo B, Ramsewak R, Khan A, Ramsubhag A, Reynolds W, Nair M..  (2010)  Identification of new limonoids from Swietenia and their biological activity against insects.,  66  (12): [PMID:20799251] [10.1002/ps.2013]

Source

Source(1):

• Scientific Literature