N,N'-(Propane-1,3-diyl)bis(7,8-dihydroxy-2-imino-2H-chromene-3-carboxamide)

ID: ALA1098764

PubChem CID: 135891379

Max Phase: Preclinical

Molecular Formula: C23H20N4O8

Molecular Weight: 480.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=c1oc2c(O)c(O)ccc2cc1C(=O)NCCCNC(=O)c1cc2ccc(O)c(O)c2oc1=N

Standard InChI:  InChI=1S/C23H20N4O8/c24-20-12(8-10-2-4-14(28)16(30)18(10)34-20)22(32)26-6-1-7-27-23(33)13-9-11-3-5-15(29)17(31)19(11)35-21(13)25/h2-5,8-9,24-25,28-31H,1,6-7H2,(H,26,32)(H,27,33)

Standard InChI Key:  WOZKPVAKLXHYED-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.0776  -26.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632  -26.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3650  -25.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6502  -25.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6468  -26.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9320  -26.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5010  -26.9775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068  -25.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916  -25.7349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094  -24.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2034  -26.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875  -26.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909  -25.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2102  -25.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724  -26.9775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782  -25.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629  -25.7349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807  -24.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502  -25.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0632  -26.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6340  -27.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3627  -27.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2 17  1  0
  5 10  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
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  8  9  1  0
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  9 10  2  0
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  8 11  2  0
  9 12  1  0
  2  3  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 12 13  1  0
 25 28  2  0
  3  6  2  0
 26 29  1  0
 12 14  2  0
 29 30  1  0
  1  2  2  0
 29 31  2  0
 13 15  1  0
 30 32  1  0
 32 16  1  0
  5  4  2  0
 19 33  1  0
 15 16  1  0
 20 34  1  0
  4  1  1  0
  3 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098764

   ---

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: 7.67

CX Basic pKa: 4.57

CX LogP: 1.57

CX LogD: 1.37

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.15

Np Likeness Score: -0.04

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