2',3',4',7-tetra-O-acetyl-6'-O-trityl loganin

ID: ALA2238092

Chembl Id: CHEMBL2238092

PubChem CID: 76319080

Max Phase: Preclinical

Molecular Formula: C43H46O15

Molecular Weight: 802.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(c3ccccc3)(c3ccccc3)c3ccccc3)[C@@H](OC(=O)O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@@H]2[C@@H](C)[C@@H](OC(C)=O)C[C@H]12

Standard InChI:  InChI=1S/C43H46O15/c1-24-33(53-25(2)44)21-31-32(39(47)50-5)22-51-40(35(24)31)58-41-38(55-27(4)46)37(54-26(3)45)36(57-42(48)49)34(56-41)23-52-43(28-15-9-6-10-16-28,29-17-11-7-12-18-29)30-19-13-8-14-20-30/h6-20,22,24,31,33-38,40-41H,21,23H2,1-5H3,(H,48,49)/t24-,31+,33-,34+,35+,36+,37-,38+,40-,41-/m0/s1

Standard InChI Key:  VOMOJHSXQJPCCP-BBZFSHILSA-N

Alternative Forms

1. Parent:

   

   ALA2238092

   methyl (1S,4aS,6S,7R,7aS)-6-acetyloxy-1-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-5-carboxyoxy-6-(trityloxymethyl)oxan-2-yl]oxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

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: 802.83

Molecular Weight (Monoisotopic): 802.2837

AlogP: 5.28

#Rotatable Bonds: 13

Polar Surface Area: 188.65

Molecular Species: ACID

HBA: 14

HBD: 1

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.33

CX Basic pKa: ┄

CX LogP: 6.20

CX LogD: 5.09

Aromatic Rings: 3

Heavy Atoms: 58

QED Weighted: 0.13

Np Likeness Score: 1.34

References

1. Khan M, Garg A, Srivastava SK, Darokar MP.  (2012)  A cytotoxic agent from Strychnos nux-vomica and biological evaluation of its modified analogues,  21  (10): [10.1007/s00044-011-9832-9]

Source

Source(1):

• Scientific Literature