5-(2-(2-(2-(2-Ethyl-3-hydroxy-4-oxopyridin-1(4H)-yl)ethoxy)-ethoxy)ethoxy)-2,5-dioxopentan-1-aminium Chloride

ID: ALA4066692

PubChem CID: 137631714

Max Phase: Preclinical

Molecular Formula: C18H29ClN2O7

Molecular Weight: 384.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(O)c(=O)ccn1CCOCCOCCOC(=O)CCC(=O)CN.Cl

Standard InChI:  InChI=1S/C18H28N2O7.ClH/c1-2-15-18(24)16(22)5-6-20(15)7-8-25-9-10-26-11-12-27-17(23)4-3-14(21)13-19;/h5-6,24H,2-4,7-13,19H2,1H3;1H

Standard InChI Key:  FWSHPZFARNKHOY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   14.8893  -10.6071    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1323   -8.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1323   -9.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -9.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5583   -9.1927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5583   -8.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -7.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4156   -7.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -9.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453  -10.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1298  -10.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2733   -9.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -9.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -9.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4161   -9.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1310   -9.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8470   -9.1989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5619   -9.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2780   -9.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9929   -9.6127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7048   -9.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4196   -9.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7060   -8.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1358   -9.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8506   -9.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5667   -9.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8494  -10.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2816   -9.6189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  2  8  2  0
  3  9  1  0
  4 10  1  0
 10 11  1  0
  5 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 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: 384.43

Molecular Weight (Monoisotopic): 384.1897

AlogP: 0.00

#Rotatable Bonds: 14

Polar Surface Area: 130.08

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.54

CX Basic pKa: 7.83

CX LogP: 0.02

CX LogD: -0.55

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.34

Np Likeness Score: -0.30

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