desglucouzarin

ID: ALA449767

Chembl Id: CHEMBL449767

PubChem CID: 15558779

Max Phase: Preclinical

Molecular Formula: C29H44O9

Molecular Weight: 536.66

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Deglucouzarin | Desglucouzarin | Deglucouzarin|CHEMBL449767|C29H44O9

Canonical SMILES:  C[C@]12CC[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O

Standard InChI:  InChI=1S/C29H44O9/c1-27-8-5-17(37-26-25(34)24(33)23(32)21(13-30)38-26)12-16(27)3-4-20-19(27)6-9-28(2)18(7-10-29(20,28)35)15-11-22(31)36-14-15/h11,16-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t16-,17-,18+,19-,20+,21+,23+,24-,25+,26+,27-,28+,29-/m0/s1

Standard InChI Key:  CMHWMOGWFZWDMR-UEVATAMWSA-N

Alternative Forms

1. Parent:

   

   ALA449767

   DESGLUCOUZARIN

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: 536.66

Molecular Weight (Monoisotopic): 536.2985

AlogP: 1.43

#Rotatable Bonds: 4

Polar Surface Area: 145.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.18

CX Basic pKa: 0.24

CX LogP: 1.30

CX LogD: 0.87

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: 3.02

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. Araya JJ, Kindscher K, Timmermann BN..  (2012)  Cytotoxic cardiac glycosides and other compounds from Asclepias syriaca.,  75  (3): [PMID:22316168] [10.1021/np2008076]

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]

4. Pederson PJ,Cai S,Carver C,Powell DR,Risinger AL,Grkovic T,O'Keefe BR,Mooberry SL,Cichewicz RH.  (2020)  Triple-Negative Breast Cancer Cells Exhibit Differential Sensitivity to Cardenolides from Calotropis gigantea.,  83  (7.0): [PMID:32649211] [10.1021/acs.jnatprod.0c00423]

Source

Source(1):

• Scientific Literature