4-[14-Hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one

ID: ALA1159613

PubChem CID: 46905254

Max Phase: Preclinical

Molecular Formula: C29H44O9

Molecular Weight: 536.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CCC(O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)CC1CCC1C2CC[C@]2(C)C(C3=CC(=O)OC3)CCC12O

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?/m1/s1

Standard InChI Key:  CMHWMOGWFZWDMR-YYFQVYEJSA-N

Molfile:  

     RDKit          2D

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  1  2  1  0
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  6 27  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1159613

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

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. Rathore H, From AH, Ahmed K, Fullerton DS..  (1986)  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity.,  29  (10): [PMID:3020248] [10.1021/jm00160a025]

2. Rathore H, From AH, Ahmed K, Fullerton DS..  (1986)  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity.,  29  (10): [PMID:3020248] [10.1021/jm00160a025]

Source

Source(1):

• Scientific Literature