(1R,3S)-N1-((5S,6S,11aR,11bS)-2-Oxo-2,4,5,6,9,10,11,11aoctahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-5-yl)-N3-((5S,6S,11aS,11bS)-2-oxo-2,4,5,6,9,10,11,11a-octahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-5-yl)-N1,N3-dipropylcyclohexane-1,3-dicarboxamide

ID: ALA4172840

PubChem CID: 145950770

Max Phase: Preclinical

Molecular Formula: C40H56N4O6

Molecular Weight: 688.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN(C(=O)[C@H]1CCC[C@@H](C(=O)N(CCC)[C@H]2CC3=CC(=O)O[C@@]34C[C@@H]2N2CCCC[C@@H]24)C1)[C@@H]1CC2=CC(=O)O[C@@]23C[C@@H]1N1CCCC[C@@H]13

Standard InChI:  InChI=1S/C40H56N4O6/c1-3-14-43(29-19-27-21-35(45)49-39(27)23-31(29)41-16-7-5-12-33(39)41)37(47)25-10-9-11-26(18-25)38(48)44(15-4-2)30-20-28-22-36(46)50-40(28)24-32(30)42-17-8-6-13-34(40)42/h21-22,25-26,29-34H,3-20,23-24H2,1-2H3/t25-,26+,29+,30-,31-,32-,33+,34+,39-,40-/m0/s1

Standard InChI Key:  LPMPZJGXVWGHDV-ZFZAKILISA-N

Molfile:  

     RDKit          2D

 54 62  0  0  0  0  0  0  0  0999 V2000
   17.9504  -17.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6699  -18.2806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3803  -17.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0962  -18.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8087  -17.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6724  -19.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9345  -19.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8228  -20.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4399  -20.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1503  -20.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5478  -21.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3918  -21.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8355  -20.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4330  -20.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5906  -20.1003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4256  -19.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5329  -19.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0059  -19.0682    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7036  -21.5416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.0994  -21.7128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2776  -21.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1182  -20.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7112  -22.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9428  -17.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0124  -18.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9991  -17.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2646  -16.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0363  -16.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0726  -15.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3279  -15.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1105  -14.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8290  -16.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6880  -17.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6626  -17.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3860  -18.2925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3853  -19.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0979  -19.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0972  -20.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0993  -17.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8160  -18.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8111  -19.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5224  -19.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2371  -19.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2381  -18.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5218  -17.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1000  -17.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0239  -17.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2086  -17.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7506  -18.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1085  -18.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9162  -18.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3751  -18.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6578  -16.6623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0110  -19.1139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  2  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 14 15  1  0
 15 10  1  0
 15 16  1  0
 16 17  1  0
  9 17  1  6
 16 18  1  6
  6 16  1  0
 10 19  1  1
 20  9  1  0
 21 20  1  0
 22 21  1  0
 22  8  2  0
 23 21  2  0
  1 24  2  0
 25 26  1  0
 27 26  1  6
 28 27  1  0
 29 28  2  0
 29 30  1  0
 31 30  2  0
 30 32  1  0
 32 27  1  0
 33 28  1  0
 34 33  1  0
 34 25  1  0
 34 35  1  6
 35 36  1  0
 36 37  1  0
 37 38  1  0
 35 39  1  0
 40 39  1  1
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 40  1  0
 39 46  2  0
 47 27  1  0
 48 47  1  0
 49 48  1  0
 50 49  1  0
 51 50  1  0
 51 52  1  0
 52 25  1  0
 52 47  1  0
 47 53  1  1
 25 54  1  6
 44  1  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4172840

   ---

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: 688.91

Molecular Weight (Monoisotopic): 688.4200

AlogP: 4.51

#Rotatable Bonds: 8

Polar Surface Area: 99.70

Molecular Species: BASE

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.60

CX LogP: 4.26

CX LogD: 0.48

Aromatic Rings: ┄

Heavy Atoms: 50

QED Weighted: 0.34

Np Likeness Score: 0.55

References

1. Hou W, Lin H, Wang ZY, Banwell MG, Zeng T, Sun PH, Lin J, Chen WM..  (2017)  Novel bivalent securinine mimetics as topoisomerase I inhibitors.,  8  (2): [PMID:30108747] [10.1039/C6MD00563B]

Source

Source(1):

• Scientific Literature