3,3'-(2,2'-(4-Methoxyphenylazanediyl)bis(ethane-2,1-diyl))-bis-(4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide)

ID: ALA2419260

PubChem CID: 44255959

Max Phase: Preclinical

Molecular Formula: C21H21N13O5

Molecular Weight: 535.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N(CCn2nnc3c(C(N)=O)ncn3c2=O)CCn2nnc3c(C(N)=O)ncn3c2=O)cc1

Standard InChI:  InChI=1S/C21H21N13O5/c1-39-13-4-2-12(3-5-13)30(6-8-33-20(37)31-10-24-14(16(22)35)18(31)26-28-33)7-9-34-21(38)32-11-25-15(17(23)36)19(32)27-29-34/h2-5,10-11H,6-9H2,1H3,(H2,22,35)(H2,23,36)

Standard InChI Key:  WVBQIOMSBAUBRB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.0838  -28.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5843  -29.8163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA2419260

   3-[2-[N-[2-(8-carbamoyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3-yl)ethyl]-4-methoxyanilino]ethyl]-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

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: 535.49

Molecular Weight (Monoisotopic): 535.1789

AlogP: -2.70

#Rotatable Bonds: 10

Polar Surface Area: 228.81

Molecular Species: NEUTRAL

HBA: 16

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.16

CX Basic pKa: 3.16

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: 5

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: -1.08

References

1. Pletsas D, Garelnabi EA, Li L, Phillips RM, Wheelhouse RT..  (2013)  Synthesis and quantitative structure-activity relationship of imidazotetrazine prodrugs with activity independent of O6-methylguanine-DNA-methyltransferase, DNA mismatch repair, and p53.,  56  (17): [PMID:23895620] [10.1021/jm401121k]

Source

Source(1):

• Scientific Literature