4alpha-(furoic-2-acyl)-4-desoxy-podophyllotoxin

ID: ALA3925676

PubChem CID: 134141950

Max Phase: Preclinical

Molecular Formula: C27H24O10

Molecular Weight: 508.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@H](OC(=O)c3ccco3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C27H24O10/c1-30-20-7-13(8-21(31-2)25(20)32-3)22-14-9-18-19(36-12-35-18)10-15(14)24(16-11-34-27(29)23(16)22)37-26(28)17-5-4-6-33-17/h4-10,16,22-24H,11-12H2,1-3H3/t16-,22+,23-,24-/m0/s1

Standard InChI Key:  NUHXIHVEMQHVAM-ZFIFVKQDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3925676

   ---

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: 508.48

Molecular Weight (Monoisotopic): 508.1369

AlogP: 3.87

#Rotatable Bonds: 6

Polar Surface Area: 111.89

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.18

CX LogD: 3.18

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.46

Np Likeness Score: 1.07

References

1. Zhang L, Zhang Z, Chen F, Chen Y, Lin Y, Wang J..  (2016)  Aromatic heterocyclic esters of podophyllotoxin exert anti-MDR activity in human leukemia K562/ADR cells via ROS/MAPK signaling pathways.,  123  [PMID:27484511] [10.1016/j.ejmech.2016.07.050]

2. Xiao J, Gao M, Sun Z, Diao Q, Wang P, Gao F..  (2020)  Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020).,  208  [PMID:32992133] [10.1016/j.ejmech.2020.112830]

Source

Source(1):

• Scientific Literature