1-((2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yloxy)-3-(4-(9-fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)imidazo[1,2-a]pyridin-1-ium

ID: ALA3542226

PubChem CID: 118753388

Max Phase: Preclinical

Molecular Formula: C34H34FN6O10+

Molecular Weight: 705.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(c2c[n+](O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c3ccccn23)=C1c1cn2c3c(cc(F)cc13)CN(C(=O)N1CCCCC1)CC2

Standard InChI:  InChI=1S/C34H33FN6O10/c35-18-12-17-14-39(34(49)37-7-3-1-4-8-37)11-10-38-15-20(19(13-18)25(17)38)23-24(31(46)36-30(23)45)21-16-41(22-6-2-5-9-40(21)22)51-33-28(44)26(42)27(43)29(50-33)32(47)48/h2,5-6,9,12-13,15-16,26-29,33,42-44H,1,3-4,7-8,10-11,14H2,(H-,36,45,46,47,48)/p+1/t26-,27-,28+,29-,33-/m0/s1

Standard InChI Key:  JQKLRWNJRDNNQC-CNCMDCEZSA-O

Molfile:  

     RDKit          2D

 51 58  0  0  0  0  0  0  0  0999 V2000
   15.6874  -15.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1166  -14.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5271  -15.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5062  -16.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3832  -16.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8433  -17.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3888  -15.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1034  -15.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8125  -15.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7992  -16.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0846  -16.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0770  -17.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9830  -12.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8002  -12.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0546  -11.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3916  -11.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7329  -11.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4992  -13.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7506  -13.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2800  -13.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0266  -13.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6872  -14.3095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0972  -13.0524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3452  -13.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1406  -14.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6889  -13.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4362  -12.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6413  -12.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6792  -13.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1326  -12.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3350  -12.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0871  -13.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4305  -13.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0890  -14.3036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1264  -15.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6389  -14.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5129  -15.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3171  -14.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7083  -15.5165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7853  -12.0096    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.8321  -11.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9556  -11.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2282  -16.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4188  -16.0927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5609  -16.9242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0835  -17.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4130  -18.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2256  -18.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7078  -17.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3774  -17.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4041  -18.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
 11  5  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
  7  1  1  1
  8  2  1  6
  9  3  1  1
 10  4  1  6
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 18 29  1  0
 34 19  1  0
 19 18  2  0
 13 18  1  0
 20 21  2  0
 21 22  1  0
 22 24  2  0
 23 20  1  0
 14 20  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 33 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 36  2  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 35 37  1  0
 36 38  1  0
 37 39  1  0
 38 39  1  0
 31 40  1  0
 15 41  2  0
 17 42  2  0
 39 43  1  0
 43 44  2  0
 43 45  1  0
 45 46  1  0
 45 50  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 22  1  1  0
 12 51  2  0
M  CHG  1  22   1
M  END

Alternative Forms

1. Parent:

   

   ALA3542226

   ---

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: 705.68

Molecular Weight (Monoisotopic): 705.2315

AlogP: -0.37

#Rotatable Bonds: 5

Polar Surface Area: 199.39

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.77

CX Basic pKa: ┄

CX LogP: -2.76

CX LogD: -1.99

Aromatic Rings: 4

Heavy Atoms: 51

QED Weighted: 0.13

Np Likeness Score: -0.05

References

1. Zamek-Gliszczynski MJ, Abraham TL, Alberts JJ, Kulanthaivel P, Jackson KA, Chow KH, McCann DJ, Hu H, Anderson S, Furr NA, Barbuch RJ, Cassidy KC..  (2013)  Pharmacokinetics, metabolism, and excretion of the glycogen synthase kinase-3 inhibitor LY2090314 in rats, dogs, and humans: a case study in rapid clearance by extensive metabolism with low circulating metabolite exposure.,  41  (4): [PMID:23305709] [10.1124/dmd.112.048488]

Source

Source(1):

• Scientific Literature