4beta-(E)-3-(4-Nitrophenyl)-2-(3,4,5-trimethoxyphenyl)acrylamido podophyllotoxin

ID: ALA1813296

PubChem CID: 56681900

Max Phase: Preclinical

Molecular Formula: C40H38N2O13

Molecular Weight: 754.75

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: COc1cc(/C(=C\c2ccc([N+](=O)[O-])cc2)C(=O)N[C@@H]2c3cc4c(cc3[C@@H](c3cc(OC)c(OC)c(OC)c3)[C@H]3C(=O)OC[C@@H]32)OCO4)cc(OC)c1OC

Standard InChI: InChI=1S/C40H38N2O13/c1-47-30-12-21(13-31(48-2)37(30)51-5)24(11-20-7-9-23(10-8-20)42(45)46)39(43)41-36-26-17-29-28(54-19-55-29)16-25(26)34(35-27(36)18-53-40(35)44)22-14-32(49-3)38(52-6)33(15-22)50-4/h7-17,27,34-36H,18-19H2,1-6H3,(H,41,43)/b24-11+/t27-,34+,35-,36+/m0/s1

Standard InChI Key: XPGHMXHCFFNSCN-KCIZRZKISA-N

Molfile:

     RDKit          2D

 57 63  0  0  0  0  0  0  0  0999 V2000
    9.9527   -9.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9516  -10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6664  -10.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3828  -10.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3800   -9.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6646   -8.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6662  -11.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3806  -11.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804  -12.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947  -13.0822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0921  -11.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8068  -11.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5208  -11.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5215  -10.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8021  -10.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0910  -10.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658  -13.0819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0945  -13.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0898  -15.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0865  -16.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3686  -16.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0743  -18.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7922  -17.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3633  -17.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -16.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6457  -18.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9344  -17.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0679  -18.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3502  -19.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5036  -18.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4975  -18.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8101  -14.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8098  -15.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5946  -15.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0801  -14.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5951  -14.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8493  -16.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3773  -15.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3823  -14.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6774  -13.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6714  -15.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9659  -15.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9642  -14.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1829  -14.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7017  -14.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1857  -15.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7994   -9.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5125   -8.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2355  -10.1949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9504  -10.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2350  -11.8471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2344  -12.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8042  -13.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8042  -15.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6606   -8.1231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9449   -7.7127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3738   -7.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 24 26  1  0
  1  2  2  0
 26 27  1  0
 13 14  2  0
 22 28  1  0
  3  7  1  0
 28 29  1  0
 14 15  1  0
 23 30  1  0
  3  4  2  0
 30 31  1  0
 32 33  1  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
  7  8  2  0
  9 17  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 32 36  1  0
 34 37  2  0
 18 10  1  1
 18 39  1  0
 38 39  2  0
  8  9  1  0
 39 40  1  0
 40 43  2  0
 18 32  1  0
 42 41  2  0
 41 38  1  0
 42 43  1  0
 38 19  1  0
 19 33  1  0
  4  5  1  0
 19 20  1  6
 20 21  2  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 42  1  0
  9 10  1  0
 15 47  1  0
 22 23  1  0
 47 48  1  0
  2  3  1  0
 14 49  1  0
  5  6  2  0
 49 50  1  0
 11 12  2  0
 13 51  1  0
  6  1  1  0
 51 52  1  0
 20 25  1  0
 32 53  1  6
 21 24  1  0
 33 54  1  1
 24 22  2  0
 23 25  2  0
 12 13  1  0
 55 56  2  0
 55 57  1  0
  6 55  1  0
M  CHG  2  55   1  57  -1
M  END

Associated Targets(Human)

ZR-75-1 (953 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

COLO 205 (50209 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HOP-62 (47048 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A2780 (11979 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 754.75	Molecular Weight (Monoisotopic): 754.2374	AlogP: 5.71	#Rotatable Bonds: 12
Polar Surface Area: 172.38	Molecular Species: NEUTRAL	HBA: 13	HBD: 1
#RO5 Violations: 3	HBA (Lipinski): 15	HBD (Lipinski): 1	#RO5 Violations (Lipinski): 3
CX Acidic pKa: ┄	CX Basic pKa: ┄	CX LogP: 4.83	CX LogD: 4.83
Aromatic Rings: 4	Heavy Atoms: 55	QED Weighted: 0.06	Np Likeness Score: 0.48

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]

4beta-(E)-3-(4-Nitrophenyl)-2-(3,4,5-trimethoxyphenyl)acrylamido podophyllotoxin

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source