4beta-(E)-2-(2-Methoxyphenyl)-3-(2-nitrophenyl)acrylamido podophyllotoxin

ID: ALA1813301

PubChem CID: 56657975

Max Phase: Preclinical

Molecular Formula: C38H34N2O11

Molecular Weight: 694.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1/C=C(/C(=O)N[C@@H]1c2cc3c(cc2[C@@H](c2cc(OC)c(OC)c(OC)c2)[C@H]2C(=O)OC[C@@H]21)OCO3)c1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C38H34N2O11/c1-45-28-12-8-5-9-20(28)13-25(22-10-6-7-11-27(22)40(43)44)37(41)39-35-24-17-30-29(50-19-51-30)16-23(24)33(34-26(35)18-49-38(34)42)21-14-31(46-2)36(48-4)32(15-21)47-3/h5-17,26,33-35H,18-19H2,1-4H3,(H,39,41)/b25-13+/t26-,33+,34-,35+/m0/s1

Standard InChI Key:  HPVQEJICFXVZJM-PMPNLIMNSA-N

Molfile:  

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M  CHG  2   1   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1813301

   (E)-N-[(5S,5aS,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]-3-(2-methoxyphenyl)-2-(2-nitrophenyl)prop-2-enamide

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: 694.69

Molecular Weight (Monoisotopic): 694.2163

AlogP: 5.69

#Rotatable Bonds: 10

Polar Surface Area: 153.92

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.42

CX Basic pKa: ┄

CX LogP: 5.14

CX LogD: 5.14

Aromatic Rings: 4

Heavy Atoms: 51

QED Weighted: 0.07

Np Likeness Score: 0.39

References

1. Kamal A, Suresh P, Janaki Ramaiah M, Mallareddy A, Kumar BA, Raju P, Vinay Gopal J, Pushpavalli SN, Lavanya A, Sarma P, Pal-Bhadra M..  (2011)  Synthesis and biological evaluation of 4β-acrylamidopodophyllotoxin congeners as DNA damaging agents.,  19  (15): [PMID:21737288] [10.1016/j.bmc.2011.06.017]

Source

Source(1):

• Scientific Literature