ID: ALA510917

Max Phase: Preclinical

Molecular Formula: C39H50O18

Molecular Weight: 806.81

Molecule Type: Small molecule

Representations

Synonyms (1): Prieurianin Acetate
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C1[C@@H]([C@@]2(C)[C@@H](OC(=O)O)CC(=O)O[C@](C)(COC(C)=O)[C@@H]2CC(=O)OC)[C@@H](OC=O)[C@H](OC(=O)[C@H](OC(C)=O)[C@H](C)CC)[C@]2(C)[C@@H](c3ccoc3)CC(=O)[C@]12O

Standard InChI:  InChI=1S/C39H50O18/c1-10-19(2)31(54-22(5)42)34(46)56-33-32(53-18-40)30(20(3)39(49)26(43)13-24(38(33,39)8)23-11-12-51-16-23)37(7)25(14-28(44)50-9)36(6,17-52-21(4)41)57-29(45)15-27(37)55-35(47)48/h11-12,16,18-19,24-25,27,30-33,49H,3,10,13-15,17H2,1-2,4-9H3,(H,47,48)/t19-,24-,25+,27+,30-,31-,32-,33+,36-,37-,38+,39-/m1/s1

Standard InChI Key:  ITIUHHJPOCVRDD-MGVQCJDMSA-N

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

Properties

Molecular Weight: 806.81

Molecular Weight (Monoisotopic): 806.2997

AlogP: 3.21

#Rotatable Bonds: 14

Polar Surface Area: 254.77

Molecular Species: ACID

HBA: 17

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.33

CX Basic pKa:

CX LogP: 2.76

CX LogD: 1.66

Aromatic Rings: 1

Heavy Atoms: 57

QED Weighted: 0.12

Np Likeness Score: 2.51

References

1. Lidert Z, Taylor DAH, Thirugnanam M.  (1985)  Insect Antifeedant Activity of Four Prieurianin-Type Limonoids,  48  (5): [10.1021/np50041a029]

2. Koul O, Daniewski WM, Multani JS, Gumulka M, Singh G..  (2003)  Antifeedant effects of the limonoids from Entandrophragma candolei (Meliaceae) on the gram pod borer, Helicoverpa armigera (Lepidoptera: Noctuidae).,  51  (25): [PMID:14640569] [10.1021/jf0304223]

Source

Source(1):

• Scientific Literature