Preferred name
PSI-697
Synonyms
P-Selectin Inhibitor ()
WAY-197697 ()
P&D ID
PD058179
CAS
851546-61-7
Tags
available
drug candidate
Drug indication
Thrombosis
Atherosclerosis
Drug Status
investigational
Max Phase
1.0
Structure
SMILES
O=C(O)c1c(O)c(Cc2ccc(Cl)cc2)nc2c3c(ccc12)CCCC3
InChI
InChI=1S/C21H18ClNO3/c22-14-8-5-12(6-9-14)11-17-20(24)18(21(25)26)16-10-7-13-3-1-2-4-15(13)19(16)23-17/h5-10,24H,1-4,11H2,(H,25,26)
InChIkey
DIEPFYNZGUUVHD-UHFFFAOYSA-N
MOL
PSI-697
RDKit 2D
26 29 0 0 0 0 0 0 0 0999 V2000
-1.5000 -7.7942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-5.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-7.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-8.2500 1.2990 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
-8.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-7.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
2 4 1 0
4 5 2 0
5 6 1 0
5 7 1 0
7 8 1 0
8 9 1 0
9 10 2 0
10 11 1 0
11 12 2 0
12 13 1 0
12 14 1 0
14 15 2 0
7 16 2 0
16 17 1 0
17 18 2 0
18 19 1 0
19 20 2 0
20 21 1 0
21 22 2 0
19 23 1 0
23 24 1 0
24 25 1 0
25 26 1 0
22 4 1 0
15 9 1 0
22 17 1 0
26 18 1 0
M END
> <ID>
PD058179
> <Name>
PSI-697
0
0
3
2022
Structural modification aimed for improving solubility of lead compounds in early phase drug discovery.
Das B, Baidya ATK et al. Bioorg Med Chem
2010
Discovery of 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury.
Huang A, Moretto A et al. J. Med. Chem.
6
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugMAP
MedChem Express Bioactive Compound Library
ReFrame library
3
Mcule
MedChem Express Bioactive Compound Library
18
ChEMBL CHEMBL219046
PubChem 12004316
ZINC ZINC000028603970
BindingDB 50201984
ChemSpider 10176783
ClinicalTrials.gov PSI-697
COCONUT CNP0513133.0
DrugBank DB12211
FDA SRS LH1XC916ME
GSRS f2eae0fe-89f0-4...
HMDB HMDB0256897
IBM NIH F6946DE18C2EC48...
Mcule MCULE-6722883206
PubChem TPS 17503603
Reactome 10176783
SureChEMBL SCHEMBL43527
(calculated by RDKit )
Molecular Weight
367.1
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
3
Ring Count
4
Aromatic Ring Count
3
cLogP
4.76
TPSA
70.42
Fraction CSP3
0.24
Chiral centers
0.0
Largest ring
6.0
QED
0.7
0
No structural alerts detected
(extracted from source data)
MOA
P selectin inhibitor
Pathway
Immunology/Inflammation
Target
P-selectin
