3-{[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid

ID: ALA32960

Chembl Id: CHEMBL32960

PubChem CID: 9885190

Max Phase: Preclinical

Molecular Formula: C19H25N3O4

Molecular Weight: 359.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: L-709780 | L-709780|CHEMBL32960|BDBM50078448|l709780|3-{[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid|3-{[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid(L-709780)

Canonical SMILES:  O=C(O)CCNC(=O)c1ccc2c(c1)C(=O)N(CCC1CCNCC1)C2

Standard InChI:  InChI=1S/C19H25N3O4/c23-17(24)5-9-21-18(25)14-1-2-15-12-22(19(26)16(15)11-14)10-6-13-3-7-20-8-4-13/h1-2,11,13,20H,3-10,12H2,(H,21,25)(H,23,24)

Standard InChI Key:  YAAYYZAARZCUQN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA32960

   3-{[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic 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: 359.43

Molecular Weight (Monoisotopic): 359.1845

AlogP: 1.24

#Rotatable Bonds: 7

Polar Surface Area: 98.74

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.18

CX Basic pKa: 10.36

CX LogP: -2.19

CX LogD: -2.19

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.68

Np Likeness Score: -0.40

References

1. Egbertson M, Bednar B, Bednar R, Hartman G, Gould R, Lynch R, Vassallo L, Young S.  (1996)  Non-peptide glycoprotein IIb/IIIa inhibitors. 9. Centrally constrained alpha-sulfonamides are useful tools for exploring platelet receptor function,  6  (12): [10.1016/0960-894X(96)00242-9]

2. Egbertson M, Naylor A, Hartman G, Cook J, Gould R, Holahan M, Lynch J, Lynch R, Stranieri M, Vassallo L.  (1994)  Non-peptide fibrinogen receptor antagonists. 3. design and discovery of a centrally constrained inhibitor,  4  (15): [10.1016/S0960-894X(01)80380-2]

3. Naylor A, Egbertson M, Vassallo L, Birchenough L, Zhang G, Gould R, Hartman G.  (1994)  Non-peptide fibrinogen receptor antagonists. 4. Proposed three-dimensional requirements in centrally constrained inhibitors.,  4  (15): [10.1016/S0960-894X(01)80381-4]

4. Egbertson MS, Bednar B, Askew BC, Bednar RA, Brashear K, Breslin MJ, Duggan ME, Fisher TE, Halczenko W, Hutchinson JH, Ihle N, Prugh JD, Wai JS, Gould RJ, Hartman GD..  (2000)  Nonpeptide GPIIB/IIIA receptor antagonists. Part 21: C-6 flexibility and amide bond orientation are important factors in determining the affinity of compounds for activated or resting platelet receptors.,  10  (17): [PMID:10987423] [10.1016/s0960-894x(00)00385-1]

5. Egbertson MS, Cook JJ, Bednar B, Prugh JD, Bednar RA, Gaul SL, Gould RJ, Hartman GD, Homnick CF, Holahan MA, Libby LA, Lynch JJ, Lynch RJ, Sitko GR, Stranieri MT, Vassallo LM..  (1999)  Non-peptide GPIIb/IIIa inhibitors. 20. Centrally constrained thienothiophene alpha-sulfonamides are potent, long acting in vivo inhibitors of platelet aggregation.,  42  (13): [PMID:10395482] [10.1021/jm980722p]

6. Egbertson M, Hartman G, Gould R, Bednar B, Bednar R, Cook J, Gaul S, Holahan M, Libby L, Lynch J, Lynch R, Sitko G, Stranieri M, Vassallo L.  (1996)  Nonpeptide GPIIb/IIIa inhibitors. 10. Centrally constrained alpha-sulfonamides are potent inhibitors of platelet aggregation,  6  (21): [10.1016/0960-894X(96)00473-8]

7. Halczenko W, Cook JJ, Holahan MA, Sitko GR, Stranieri MT, Zhang G, Lynch RJ, Lynch JJ, Gould RJ, Hartman GD.  (1996)  Nonpeptide glycoprotein IIB/IIIA inhibitors. 12. Potent and orally active centrally constrained thieno[2,3-c]pyridones,  6  (22): [10.1016/S0960-894X(96)00511-2]

8. Scarborough RM, Gretler DD..  (2000)  Platelet glycoprotein IIb-IIIa antagonists as prototypical integrin blockers: novel parenteral and potential oral antithrombotic agents.,  43  (19): [PMID:10999999] [10.1021/jm000022w]

9. Krysko AA, Samoylenko GV, Polishchuk PG, Andronati SA, Kabanova TA, Khristova TM, Kuz'min VE, Kabanov VM, Krysko OL, Varnek AA, Grygorash RY..  (2011)  RGD mimetics containing phthalimidine fragment as novel ligands of fibrinogen receptor.,  21  (19): [PMID:21852128] [10.1016/j.bmcl.2011.07.063]

Source

Source(1):

• Scientific Literature