(Z)-2-((2S,4S,5R,6S)-5-acetamido-2-carboxy-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-yloxy)-1-(pyrrolidin-1-yl)diazene oxide

ID: ALA4071503

PubChem CID: 137638952

Max Phase: Preclinical

Molecular Formula: C15H26N4O10

Molecular Weight: 422.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@@H]([C@H](O)[C@H](O)CO)O[C@@](O/N=[N+](\[O-])N2CCCC2)(C(=O)O)C[C@@H]1O

Standard InChI:  InChI=1S/C15H26N4O10/c1-8(21)16-11-9(22)6-15(14(25)26,28-13(11)12(24)10(23)7-20)29-17-19(27)18-4-2-3-5-18/h9-13,20,22-24H,2-7H2,1H3,(H,16,21)(H,25,26)/b19-17-/t9-,10+,11+,12+,13-,15-/m0/s1

Standard InChI Key:  QPEZUULJIGKBQQ-PAGMXWTISA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   17.7625   -4.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3518   -5.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1771   -5.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9290   -5.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9290   -6.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6420   -6.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3550   -6.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6420   -4.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3435   -3.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5879   -4.4546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5960   -5.8853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4214   -5.8806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8361   -6.5937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8280   -5.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6420   -7.2344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2182   -6.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2165   -4.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2194   -7.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5046   -7.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9313   -7.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2141   -3.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5022   -5.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9242   -3.5260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4974   -3.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4950   -2.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2155   -5.5834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.5071   -7.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1218   -7.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8350   -7.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6608   -6.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  5  1  0
  4  8  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  2  8  1  0
  1  9  1  0
  1 10  2  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
  6 15  1  6
  5 16  1  1
  4 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 17 21  1  0
 17 22  1  6
 21 23  1  1
 21 24  1  0
 24 25  1  0
  4 26  1  6
 13 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 13  1  0
M  CHG  2  12   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4071503

   ---

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: 422.39

Molecular Weight (Monoisotopic): 422.1649

AlogP: -2.96

#Rotatable Bonds: 8

Polar Surface Area: 207.45

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.92

CX Basic pKa: ┄

CX LogP: -5.63

CX LogD: -7.13

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.13

Np Likeness Score: 0.77

References

1. Huang Z, Fu J, Zhang Y..  (2017)  Nitric Oxide Donor-Based Cancer Therapy: Advances and Prospects.,  60  (18): [PMID:28505442] [10.1021/acs.jmedchem.6b01672]

Source

Source(1):

• Scientific Literature