ID: ALA1789965

Max Phase: Preclinical

Molecular Formula: C48H78O19

Molecular Weight: 959.13

Molecule Type: Small molecule

Representations

Synonyms (1): Asiaticoside
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H]1[C@H](C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@H]12

Standard InChI:  InChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22-,24-,25-,26-,27-,28-,29+,30+,31-,32-,33+,34-,35-,36-,37-,38-,39+,40-,41+,42+,44+,45+,46-,47-,48+/m1/s1

Standard InChI Key:  WYQVAPGDARQUBT-JVGKFWCXSA-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: 959.13

Molecular Weight (Monoisotopic): 958.5137

AlogP: -1.03

#Rotatable Bonds: 9

Polar Surface Area: 315.21

Molecular Species: NEUTRAL

HBA: 19

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.87

CX Basic pKa:

CX LogP: -0.54

CX LogD: -0.54

Aromatic Rings: 0

Heavy Atoms: 67

QED Weighted: 0.10

Np Likeness Score: 2.61

References

1. Jew SS, Yoo CH, Lim DY, Kim H, Mook-Jung I, Jung MW, Choi H, Jung YH, Kim H, Park HG..  (2000)  Structure-activity relationship study of asiatic acid derivatives against beta amyloid (A beta)-induced neurotoxicity.,  10  (2): [PMID:10673093] [10.1016/s0960-894x(99)00658-7]

2. Wen X, Sun H, Liu J, Cheng K, Zhang P, Zhang L, Hao J, Zhang L, Ni P, Zographos SE, Leonidas DD, Alexacou KM, Gimisis T, Hayes JM, Oikonomakos NG..  (2008)  Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.,  51  (12): [PMID:18517260] [10.1021/jm8000949]

3. Nhiem NX, Tai BH, Quang TH, Kiem PV, Minh CV, Nam NH, Kim JH, Im LR, Lee YM, Kim YH..  (2011)  A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells.,  21  (6): [PMID:21353543] [10.1016/j.bmcl.2011.01.066]

Source

Source(1):

• Scientific Literature