4-(2-Oxo-hexadecanoylamino)-butyric acid

ID: ALA95190

Chembl Id: CHEMBL95190

PubChem CID: 9906670

Max Phase: Preclinical

Molecular Formula: C20H37NO4

Molecular Weight: 355.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-(2-Oxohexadecanamido)Butanoic Acid | 4-(2-oxohexadecanamido)butanoic acid|CHEMBL95190|SCHEMBL1877382|BDBM50149408|4-(2-Oxo-hexadecanoylamino)-butyric acid|PD181652

Canonical SMILES:  CCCCCCCCCCCCCCC(=O)C(=O)NCCCC(=O)O

Standard InChI:  InChI=1S/C20H37NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(22)20(25)21-17-14-16-19(23)24/h2-17H2,1H3,(H,21,25)(H,23,24)

Standard InChI Key:  GCTDVJHSYNCJRN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA95190

   4-(2-Oxohexadecanamido)butanoic acid

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: 355.52

Molecular Weight (Monoisotopic): 355.2723

AlogP: 4.63

#Rotatable Bonds: 18

Polar Surface Area: 83.47

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 5.52

CX LogD: 2.45

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.28

Np Likeness Score: 0.09

References

1. Kokotos G, Kotsovolou S, Six DA, Constantinou-Kokotou V, Beltzner CC, Dennis EA..  (2002)  Novel 2-oxoamide inhibitors of human group IVA phospholipase A(2).,  45  (14): [PMID:12086476] [10.1021/jm025538p]

2. Kokotos G, Six DA, Loukas V, Smith T, Constantinou-Kokotou V, Hadjipavlou-Litina D, Kotsovolou S, Chiou A, Beltzner CC, Dennis EA..  (2004)  Inhibition of group IVA cytosolic phospholipase A2 by novel 2-oxoamides in vitro, in cells, and in vivo.,  47  (14): [PMID:15214789] [10.1021/jm030485c]

3. Stephens D, Barbayianni E, Constantinou-Kokotou V, Peristeraki A, Six DA, Cooper J, Harkewicz R, Deems RA, Dennis EA, Kokotos G..  (2006)  Differential inhibition of group IVA and group VIA phospholipases A2 by 2-oxoamides.,  49  (9): [PMID:16640343] [10.1021/jm050993h]

4. Lee KL, Foley MA, Chen L, Behnke ML, Lovering FE, Kirincich SJ, Wang W, Shim J, Tam S, Shen MW, Khor S, Xu X, Goodwin DG, Ramarao MK, Nickerson-Nutter C, Donahue F, Ku MS, Clark JD, McKew JC..  (2007)  Discovery of Ecopladib, an indole inhibitor of cytosolic phospholipase A2alpha.,  50  (6): [PMID:17305324] [10.1021/jm061131z]

5. Six DA, Barbayianni E, Loukas V, Constantinou-Kokotou V, Hadjipavlou-Litina D, Stephens D, Wong AC, Magrioti V, Moutevelis-Minakakis P, Baker SF, Dennis EA, Kokotos G..  (2007)  Structure-activity relationship of 2-oxoamide inhibition of group IVA cytosolic phospholipase A2 and group V secreted phospholipase A2.,  50  (17): [PMID:17672443] [10.1021/jm0613673]

6. Barbayianni E, Stephens D, Grkovich A, Magrioti V, Hsu YH, Dolatzas P, Kalogiannidis D, Dennis EA, Kokotos G..  (2009)  2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides.,  17  (13): [PMID:19443224] [10.1016/j.bmc.2009.03.069]

7. Noha SM, Jazzar B, Kuehnl S, Rollinger JM, Stuppner H, Schaible AM, Werz O, Wolber G, Schuster D..  (2012)  Pharmacophore-based discovery of a novel cytosolic phospholipase A(2)α inhibitor.,  22  (2): [PMID:22192589] [10.1016/j.bmcl.2011.11.093]

8. Antonopoulou G, Magrioti V, Kokotou MG, Nikolaou A, Barbayianni E, Mouchlis VD, Dennis EA, Kokotos G..  (2016)  2-Oxoamide inhibitors of cytosolic group IVA phospholipase A2 with reduced lipophilicity.,  24  (19): [PMID:27522578] [10.1016/j.bmc.2016.07.057]

Source

Source(1):

• Scientific Literature