3-O-[alpha-L-arabinopyranosyl(1_>2)-alpha-L-arabinopyranosyl(1_>6)]-beta-D-glucopyranosyl oleanolic acid

ID: ALA1765596

Chembl Id: CHEMBL1765596

PubChem CID: 54581283

Max Phase: Preclinical

Molecular Formula: C46H74O16

Molecular Weight: 883.08

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pitheduloside C | CHEBI:67803|Pitheduloside C|CHEMBL1765596|Q27136281|3-O-[beta-D-xylopyranosyl(1->2)-alpha-L-arabinopyranosyl(1->6)]-beta-D-glucopyranosyl oleanolic acid

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](CO[C@@H]7OC[C@H](O)[C@H](O)[C@H]7O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C46H74O16/c1-41(2)14-16-46(40(55)56)17-15-44(6)22(23(46)18-41)8-9-28-43(5)12-11-29(42(3,4)27(43)10-13-45(28,44)7)61-38-35(54)33(52)32(51)26(60-38)21-59-39-36(31(50)25(48)20-58-39)62-37-34(53)30(49)24(47)19-57-37/h8,23-39,47-54H,9-21H2,1-7H3,(H,55,56)/t23-,24+,25-,26+,27-,28+,29-,30-,31-,32+,33-,34+,35+,36+,37-,38-,39-,43-,44+,45+,46-/m0/s1

Standard InChI Key:  WBBKABSSSHJZGN-WCSFHXAVSA-N

Alternative Forms

1. Parent:

   

   ALA1765596

   PITHEDULOSIDE C

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

Calculated Properties

Molecular Weight: 883.08

Molecular Weight (Monoisotopic): 882.4977

AlogP: 1.98

#Rotatable Bonds: 8

Polar Surface Area: 254.52

Molecular Species: ACID

HBA: 15

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.74

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: -0.06

Aromatic Rings: ┄

Heavy Atoms: 62

QED Weighted: 0.12

Np Likeness Score: 2.61

References

1. Zhang H, Samadi AK, Rao KV, Cohen MS, Timmermann BN..  (2011)  Cytotoxic oleanane-type saponins from Albizia inundata.,  74  (3): [PMID:21314099] [10.1021/np100702p]

2. Kakuta K, Baba M, Ito S, Kinoshita K, Koyama K, Takahashi K..  (2012)  New triterpenoid saponins from cacti and anti-type I allergy activity of saponins from cactus.,  22  (14): [PMID:22704889] [10.1016/j.bmcl.2012.05.058]

3. Ye X, Yu S, Liang Y, Huang H, Lian XY, Zhang Z..  (2014)  Bioactive triterpenoid saponins and phenolic compounds against glioma cells.,  24  (22): [PMID:25442304] [10.1016/j.bmcl.2014.09.087]

Source

Source(1):

• Scientific Literature