3beta-O-[2,4-Di-O-(alpha-L-rhamnopyranosyl)-beta-D-Glucopyranosyl]-ursolic-28-methyl ester

ID: ALA585173

Chembl Id: CHEMBL585173

PubChem CID: 44597480

Max Phase: Preclinical

Molecular Formula: C49H80O16

Molecular Weight: 925.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12CC[C@@H](C)[C@H](C)[C@H]1C1=CC[C@@H]3[C@@]4(C)CC[C@H](O[C@@H]5O[C@H](CO)[C@@H](O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)[C@H](O)[C@H]5O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2

Standard InChI:  InChI=1S/C49H80O16/c1-22-13-18-49(44(58)59-10)20-19-47(8)26(31(49)23(22)2)11-12-29-46(7)16-15-30(45(5,6)28(46)14-17-48(29,47)9)63-43-40(65-42-37(56)35(54)33(52)25(4)61-42)38(57)39(27(21-50)62-43)64-41-36(55)34(53)32(51)24(3)60-41/h11,22-25,27-43,50-57H,12-21H2,1-10H3/t22-,23+,24+,25+,27-,28+,29-,30+,31+,32+,33+,34-,35-,36-,37-,38+,39-,40-,41+,42+,43+,46+,47-,48-,49+/m1/s1

Standard InChI Key:  KOIJVPALNMERCY-KBBCXJNYSA-N

Alternative Forms

1. Parent:

   

   ALA585173

   methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahyd

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: 925.16

Molecular Weight (Monoisotopic): 924.5446

AlogP: 2.71

#Rotatable Bonds: 8

Polar Surface Area: 243.52

Molecular Species: NEUTRAL

HBA: 16

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.88

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: ┄

Heavy Atoms: 65

QED Weighted: 0.10

Np Likeness Score: 2.43

References

1. Song G, Yang S, Zhang W, Cao Y, Wang P, Ding N, Zhang Z, Guo Y, Li Y..  (2009)  Discovery of the first series of small molecule H5N1 entry inhibitors.,  52  (23): [PMID:19537689] [10.1021/jm900275m]

2. Ding N, Chen Q, Zhang W, Ren S, Guo Y, Li Y..  (2012)  Structure-activity relationships of saponin derivatives: a series of entry inhibitors for highly pathogenic H5N1 influenza virus.,  53  [PMID:22575533] [10.1016/j.ejmech.2012.04.022]

3. Song G, Shen X, Li S, Li Y, Liu Y, Zheng Y, Lin R, Fan J, Ye H, Liu S..  (2015)  Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors.,  93  [PMID:25728024] [10.1016/j.ejmech.2015.02.029]

Source

Source(1):

• Scientific Literature