Epipodophyllotoxin 4-[N-(2-propynyl)]carbamate

ID: ALA1773342

PubChem CID: 54580154

Max Phase: Preclinical

Molecular Formula: C26H25NO9

Molecular Weight: 495.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCNC(=O)O[C@@H]1c2cc3c(cc2[C@@H](c2cc(OC)c(OC)c(OC)c2)[C@H]2C(=O)OC[C@@H]21)OCO3

Standard InChI:  InChI=1S/C26H25NO9/c1-5-6-27-26(29)36-23-15-10-18-17(34-12-35-18)9-14(15)21(22-16(23)11-33-25(22)28)13-7-19(30-2)24(32-4)20(8-13)31-3/h1,7-10,16,21-23H,6,11-12H2,2-4H3,(H,27,29)/t16-,21+,22-,23+/m0/s1

Standard InChI Key:  WLGYXVZLJAOZGE-AZIXLERZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1773342

   [(5S,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] N-prop-2-ynylcarbamate

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: 495.48

Molecular Weight (Monoisotopic): 495.1529

AlogP: 2.78

#Rotatable Bonds: 6

Polar Surface Area: 110.78

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: ┄

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.48

Np Likeness Score: 0.95

References

1. Kamal A, Kumar BA, Suresh P, Juvekar A, Zingde S..  (2011)  Synthesis of 4β-carbamoyl epipodophyllotoxins as potential antitumour agents.,  19  (9): [PMID:21489802] [10.1016/j.bmc.2011.03.030]

Source

Source(1):

• Scientific Literature