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

ID: ALA1096801

PubChem CID: 135891365

Max Phase: Preclinical

Molecular Formula: C23H20N4O6

Molecular Weight: 448.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=c1oc2cc(O)ccc2cc1C(=O)NCCCNC(=O)c1cc2ccc(O)cc2oc1=N

Standard InChI:  InChI=1S/C23H20N4O6/c24-20-16(8-12-2-4-14(28)10-18(12)32-20)22(30)26-6-1-7-27-23(31)17-9-13-3-5-15(29)11-19(13)33-21(17)25/h2-5,8-11,24-25,28-29H,1,6-7H2,(H,26,30)(H,27,31)

Standard InChI Key:  VLAVPACPOLPQDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   20.1137  -21.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1149  -22.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4005  -23.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4023  -21.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6874  -21.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6840  -22.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9692  -23.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2533  -22.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2567  -21.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9760  -21.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5381  -23.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5439  -21.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8286  -21.8431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5464  -20.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1158  -21.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4006  -21.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8277  -23.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6889  -21.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6877  -22.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4022  -23.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4004  -21.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1152  -21.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1186  -22.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8335  -23.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5494  -22.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5460  -21.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8267  -21.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645  -23.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2588  -21.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9740  -21.8431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2562  -20.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6867  -21.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9749  -23.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  4  1  1  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
 20 23  2  0
  8  9  1  0
 22 21  2  0
 21 18  1  0
 22 23  1  0
  9 10  2  0
  5  6  1  0
  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
M  END

Alternative Forms

1. Parent:

   

   ALA1096801

   ---

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: 448.44

Molecular Weight (Monoisotopic): 448.1383

AlogP: 2.10

#Rotatable Bonds: 6

Polar Surface Area: 172.64

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.47

CX Basic pKa: 4.78

CX LogP: 0.88

CX LogD: 0.57

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -0.16

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