5-((6-(3-Hydroxy-2-(methylcarbamoyl)-4-oxopyridin-1(4H)-yl)-hexyl)oxy)-2,5-dioxopentan-1-aminium Chloride

ID: ALA4067704

PubChem CID: 137633629

Max Phase: Preclinical

Molecular Formula: C18H28ClN3O6

Molecular Weight: 381.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1c(O)c(=O)ccn1CCCCCCOC(=O)CCC(=O)CN.Cl

Standard InChI:  InChI=1S/C18H27N3O6.ClH/c1-20-18(26)16-17(25)14(23)8-10-21(16)9-4-2-3-5-11-27-15(24)7-6-13(22)12-19;/h8,10,25H,2-7,9,11-12,19H2,1H3,(H,20,26);1H

Standard InChI Key:  XNFIQKFVSBCMPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
    0.5893   -3.4964    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9834   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834   -4.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5544   -3.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412   -3.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226   -2.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5557   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2702   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9847   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6992   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4137   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1281   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8426   -3.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5525   -3.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2649   -3.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2691   -2.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5547   -1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8362   -2.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9851   -1.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9777   -3.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5500   -4.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8343   -4.7403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2632   -4.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8319   -5.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  2  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 22  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 20 23  2  0
 19 24  1  0
 18 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
M  END

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: 381.43

Molecular Weight (Monoisotopic): 381.1900

AlogP: 0.33

#Rotatable Bonds: 12

Polar Surface Area: 140.72

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.47

CX Basic pKa: 7.83

CX LogP: -0.10

CX LogD: -0.67

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.35

Np Likeness Score: -0.17

References

1. Battah S, Hider RC, MacRobert AJ, Dobbin PS, Zhou T..  (2017)  Hydroxypyridinone and 5-Aminolaevulinic Acid Conjugates for Photodynamic Therapy.,  60  (8): [PMID:28363026] [10.1021/acs.jmedchem.7b00346]

Source

Source(1):

• Scientific Literature