6'-O-feruloyl-desglucouzarin

ID: ALA510977

Chembl Id: CHEMBL510977

PubChem CID: 44573470

Max Phase: Preclinical

Molecular Formula: C39H52O12

Molecular Weight: 712.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)OC[C@H]2O[C@@H](O[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@@H](C6=CC(=O)OC6)CC[C@]54O)C3)[C@H](O)[C@@H](O)[C@@H]2O)ccc1O

Standard InChI:  InChI=1S/C39H52O12/c1-37-13-10-24(18-23(37)6-7-27-26(37)11-14-38(2)25(12-15-39(27,38)46)22-17-32(42)48-19-22)50-36-35(45)34(44)33(43)30(51-36)20-49-31(41)9-5-21-4-8-28(40)29(16-21)47-3/h4-5,8-9,16-17,23-27,30,33-36,40,43-46H,6-7,10-15,18-20H2,1-3H3/b9-5+/t23-,24-,25+,26-,27+,30+,33+,34-,35+,36+,37-,38+,39-/m0/s1

Standard InChI Key:  OQQLWHSEFACXNN-SDSYWWGPSA-N

Alternative Forms

1. Parent:

   

   ALA510977

   [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop

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: 712.83

Molecular Weight (Monoisotopic): 712.3459

AlogP: 3.41

#Rotatable Bonds: 8

Polar Surface Area: 181.44

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.18

CX Basic pKa: 0.24

CX LogP: 3.87

CX LogD: 3.45

Aromatic Rings: 1

Heavy Atoms: 51

QED Weighted: 0.15

Np Likeness Score: 2.47

References

1. Li JZ, Qing C, Chen CX, Hao XJ, Liu HY..  (2009)  Cytotoxicity of cardenolides and cardenolide glycosides from Asclepias curassavica.,  19  (7): [PMID:19251412] [10.1016/j.bmcl.2009.02.045]

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