6'-dehydroxyghalakinoside

ID: ALA469426

Chembl Id: CHEMBL469426

PubChem CID: 16086566

Max Phase: Preclinical

Molecular Formula: C29H42O10

Molecular Weight: 550.65

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6'-Dehydroxyghalakinoside | 6-Dehydroxyghalakinoside | 6'-dehydroxyghalakinoside|6-Dehydroxyghalakinoside|CHEMBL469426|3-[(1S,3R,5S,7R,9R,10S,12R,14R,15S,17R,18S,19R,22S,23R)-9,10,17,22-tetrahydroxy-14-(hydroxymethyl)-7,18-dimethyl-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-19-yl]-2H-furan-5-one

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

Standard InChI:  InChI=1S/C29H42O10/c1-14-7-23(32)29(35)25(37-14)38-20-9-16-3-4-18-19(27(16,13-30)11-21(20)39-29)10-22(31)26(2)17(5-6-28(18,26)34)15-8-24(33)36-12-15/h8,14,16-23,25,30-32,34-35H,3-7,9-13H2,1-2H3/t14-,16+,17-,18-,19+,20-,21-,22-,23-,25+,26+,27-,28+,29+/m1/s1

Standard InChI Key:  RGJSIZOZMBPAIL-YUVWTAJSSA-N

Alternative Forms

1. Parent:

   

   ALA469426

   6'-Dehydroxyghalakinoside

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: 550.65

Molecular Weight (Monoisotopic): 550.2778

AlogP: 0.76

#Rotatable Bonds: 2

Polar Surface Area: 155.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.31

CX Basic pKa: ┄

CX LogP: 0.42

CX LogD: 0.41

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.25

Np Likeness Score: 3.47

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. Piacente S, Masullo M, De Nève N, Dewelle J, Hamed A, Kiss R, Mijatovic T..  (2009)  Cardenolides from Pergularia tomentosa display cytotoxic activity resulting from their potent inhibition of Na+/K+-ATPase.,  72  (6): [PMID:19555122] [10.1021/np800810f]

3. 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