3'-O-beta-D-glucopyranosylcalactin

ID: ALA508988

Chembl Id: CHEMBL508988

PubChem CID: 16086565

Max Phase: Preclinical

Molecular Formula: C35H50O14

Molecular Weight: 694.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@@H](C6=CC(=O)OC6)CC[C@]54O)C[C@H]3O[C@@H]2O1

Standard InChI:  InChI=1S/C35H50O14/c1-16-9-25(48-30-29(41)28(40)27(39)24(13-36)46-30)35(43)31(45-16)47-22-11-18-3-4-21-20(33(18,15-37)12-23(22)49-35)5-7-32(2)19(6-8-34(21,32)42)17-10-26(38)44-14-17/h10,15-16,18-25,27-31,36,39-43H,3-9,11-14H2,1-2H3/t16-,18+,19-,20+,21-,22-,23-,24-,25-,27-,28+,29-,30+,31+,32-,33-,34+,35+/m1/s1

Standard InChI Key:  QHTLPWXBPOENQB-GVVIVVNYSA-N

Alternative Forms

1. Parent:

   

   ALA508988

   3'-O-beta-D-glucopyranosylcalactin

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: 694.77

Molecular Weight (Monoisotopic): 694.3201

AlogP: -0.18

#Rotatable Bonds: 5

Polar Surface Area: 210.90

Molecular Species: NEUTRAL

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.31

CX Basic pKa: 0.27

CX LogP: 0.19

CX LogD: 0.19

Aromatic Rings: ┄

Heavy Atoms: 49

QED Weighted: 0.13

Np Likeness Score: 3.32

References

1. Hamed AI, Plaza A, Balestrieri ML, Mahalel UA, Springuel IV, Oleszek W, Pizza C, Piacente S..  (2006)  Cardenolide glycosides from Pergularia tomentosa and their proapoptotic activity in Kaposi's sarcoma cells.,  69  (9): [PMID:16989527] [10.1021/np060228l]

2. Hosseini SH, Masullo M, Cerulli A, Martucciello S, Ayyari M, Pizza C, Piacente S..  (2019)  Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa.,  82  (1): [PMID:30629433] [10.1021/acs.jnatprod.8b00630]

Source

Source(1):

• Scientific Literature