N,N'-(Propane-1,3-diyl)bis(6,7-dihydroxy-2-imino-2H-chromene-3-carboxamide)

ID: ALA1094197

PubChem CID: 135891380

Max Phase: Preclinical

Molecular Formula: C23H20N4O8

Molecular Weight: 480.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=c1oc2cc(O)c(O)cc2cc1C(=O)NCCCNC(=O)c1cc2cc(O)c(O)cc2oc1=N

Standard InChI:  InChI=1S/C23H20N4O8/c24-20-12(4-10-6-14(28)16(30)8-18(10)34-20)22(32)26-2-1-3-27-23(33)13-5-11-7-15(29)17(31)9-19(11)35-21(13)25/h4-9,24-25,28-31H,1-3H2,(H,26,32)(H,27,33)

Standard InChI Key:  FKOFIPBOYPUDNV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   20.7737  -26.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0593  -27.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0611  -25.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3461  -25.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3427  -26.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6279  -27.1845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6347  -25.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1968  -27.1802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2026  -25.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4873  -25.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2052  -24.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7745  -25.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0587  -25.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7737  -25.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7771  -26.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4918  -27.1845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2078  -26.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2044  -25.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4850  -25.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9230  -27.1802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9172  -25.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6325  -25.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9146  -24.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3453  -25.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6331  -27.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6331  -25.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2 17  1  0
  5 10  1  0
  1 18  1  0
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  7  8  1  0
 19 20  2  0
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 21 24  2  0
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  2  3  1  0
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 24 25  1  0
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 26 27  1  0
 27 28  2  0
  3  6  2  0
 26 29  2  0
 12 14  2  0
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  1  2  2  0
 30 31  1  0
 13 15  1  0
 30 32  2  0
  5  4  2  0
 31 33  1  0
 33 16  1  0
 15 16  1  0
 20 34  1  0
  4  1  1  0
 19 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094197

   ---

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: 480.43

Molecular Weight (Monoisotopic): 480.1281

AlogP: 1.51

#Rotatable Bonds: 6

Polar Surface Area: 213.10

Molecular Species: NEUTRAL

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.55

CX Basic pKa: 4.61

CX LogP: 0.27

CX LogD: 0.01

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.15

Np Likeness Score: -0.13

References

1. Hill TA, Mariana A, Gordon CP, Odell LR, Robertson MJ, McGeachie AB, Chau N, Daniel JA, Gorgani NN, Robinson PJ, McCluskey A..  (2010)  Iminochromene inhibitors of dynamins I and II GTPase activity and endocytosis.,  53  (10): [PMID:20426422] [10.1021/jm100119c]

2.  (2012)  Use of dynamin ring stabilizers, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data