Acetic acid 3,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester

ID: ALA374839

Chembl Id: CHEMBL374839

Cas Number: 465-15-6

PubChem CID: 9802865

Max Phase: Preclinical

Molecular Formula: C25H36O6

Molecular Weight: 432.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1C1=CC(=O)OC1

Standard InChI:  InChI=1S/C25H36O6/c1-14(26)31-20-12-25(29)19-5-4-16-11-17(27)6-8-23(16,2)18(19)7-9-24(25,3)22(20)15-10-21(28)30-13-15/h10,16-20,22,27,29H,4-9,11-13H2,1-3H3/t16-,17+,18+,19-,20+,22+,23+,24-,25+/m1/s1

Standard InChI Key:  IWCNCUVTGOMGKG-YOVVEKLRSA-N

Alternative Forms

1. Parent:

   

   ALA374839

   Oleandrigenin

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: 432.56

Molecular Weight (Monoisotopic): 432.2512

AlogP: 3.15

#Rotatable Bonds: 2

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.82

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 1.45

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: 3.19

References

1. Hashimoto T, Rathore H, Satoh D, Hong G, Griffin JF, From AH, Ahmed K, Fullerton DS..  (1986)  Cardiac glycosides. 6. Gitoxigenin C16 acetates, formates, methoxycarbonates, and digitoxosides. Synthesis and Na+,K+-ATPase inhibitory activities.,  29  (6): [PMID:3012087] [10.1021/jm00156a017]

2. Farr CD, Tabet MR, Ball WJ, Fishwild DM, Wang X, Nair AC, Welsh WJ..  (2002)  Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.,  45  (15): [PMID:12109909] [10.1021/jm0102811]

3. Zhao M, Bai L, Wang L, Toki A, Hasegawa T, Kikuchi M, Abe M, Sakai J, Hasegawa R, Bai Y, Mitsui T, Ogura H, Kataoka T, Oka S, Tsushima H, Kiuchi M, Hirose K, Tomida A, Tsuruo T, Ando M..  (2007)  Bioactive cardenolides from the stems and twigs of Nerium oleander.,  70  (7): [PMID:17595134] [10.1021/np068066g]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Michalak K, Rárová L, Kubala M, Čechová P, Strnad M, Wicha J..  (2019)  Synthesis and evaluation of cytotoxic and Na⁺/K⁺-ATP-ase inhibitory activity of selected 5α-oleandrigenin derivatives.,  180  [PMID:31325787] [10.1016/j.ejmech.2019.07.028]

7. Michalak K,Rárová L,Kubala M,Štenclová T,Strnad M,Wicha J.  (2020)  Synthesis and evaluation of Na/K-ATP-ase inhibiting and cytotoxic in vitro activities of oleandrigenin and its selected 17β-(butenolidyl)- and 17β-(3-furyl)- analogues.,  202  [PMID:32645647] [10.1016/j.ejmech.2020.112520]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays