ID: ALA3085392

Max Phase: Preclinical

Molecular Formula: C37H48O16

Molecular Weight: 748.78

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C37H48O16/c1-10-18(2)28(43)32(44)52-31-29(50-17-38)27(19(3)37(46)24(41)13-23(36(31,37)8)22-11-12-48-15-22)35(7)25(51-21(5)40)14-26(42)53-34(6,16-49-20(4)39)30(35)33(45)47-9/h11-12,15,17-18,23,25,27-31,43,46H,3,10,13-14,16H2,1-2,4-9H3/t18-,23+,25+,27-,28-,29-,30+,31+,34-,35-,36-,37-/m1/s1

Standard InChI Key:  KEIRAXFVAMECMP-VFOAQDGDSA-N

Molecule Features

Natural Product: Yes

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: 748.78

Molecular Weight (Monoisotopic): 748.2942

AlogP: 2.12

#Rotatable Bonds: 12

Polar Surface Area: 228.47

Molecular Species: NEUTRAL

HBA: 16

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.95

CX Basic pKa:

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 1

Heavy Atoms: 53

QED Weighted: 0.13

Np Likeness Score: 2.52

References

1. Lukacova V, Polonsky J, Moretti C, Pettit GR, Schmidt JM.  (1982)  Isolation and Structure of 14,15-Epoxyprieurianin From the South American Tree Guarea guidona,  45  (3): [10.1021/np50021a010]

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

3. Pettit GR, Barton DH, Herald CL, Polonsky J, Schmidt JM, Connolly JD..  (1983)  Evaluation of limonoids against the murine P388 lymphocytic leukemia cell line.,  46  (3): [PMID:6619886] [10.1021/np50027a015]

4. 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]

5. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

6. Yan Y, Zhang JX, Huang T, Mao XY, Gu W, He HP, Di YT, Li SL, Chen DZ, Zhang Y, Hao XJ..  (2015)  Bioactive Limonoid Constituents of Munronia henryi.,  78  (4): [PMID:25798528] [10.1021/np501057f]

Source

Source(1):

• Scientific Literature