ID: ALA303561

Max Phase: Preclinical

Molecular Formula: C21H31N7O7

Molecular Weight: 493.52

Molecule Type: Protein

Representations

Canonical SMILES:  N=C(N)NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C21H31N7O7/c22-13(7-4-8-25-21(23)24)18(32)26-11-16(29)27-14(10-17(30)31)19(33)28-15(20(34)35)9-12-5-2-1-3-6-12/h1-3,5-6,13-15H,4,7-11,22H2,(H,26,32)(H,27,29)(H,28,33)(H,30,31)(H,34,35)(H4,23,24,25)/t13-,14-,15-/m0/s1

Standard InChI Key:  ARNGIGOPGOEJCH-KKUMJFAQSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 493.52

Molecular Weight (Monoisotopic): 493.2285

AlogP: -2.54

#Rotatable Bonds: 15

Polar Surface Area: 249.82

Molecular Species: ZWITTERION

HBA: 7

HBD: 9

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.47

CX Basic pKa: 11.85

CX LogP: -6.56

CX LogD: -6.70

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.07

Np Likeness Score: 0.23

References

1. Barker PL, Bullens S, Bunting S, Burdick DJ, Chan KS, Deisher T, Eigenbrot C, Gadek TR, Gantzos R, Lipari MT..  (1992)  Cyclic RGD peptide analogues as antiplatelet antithrombotics.,  35  (11): [PMID:1597855] [10.1021/jm00089a014]

2. Liu J, Zhao M, Wang C, Peng S..  (2003)  Synthesis and bioactivities of nitronyl nitroxide and RGD containing pseudopeptides.,  13  (22): [PMID:14592509] [10.1016/j.bmcl.2003.08.041]

3. Alig L, Edenhofer A, Hadváry P, Hürzeler M, Knopp D, Müller M, Steiner B, Trzeciak A, Weller T..  (1992)  Low molecular weight, non-peptide fibrinogen receptor antagonists.,  35  (23): [PMID:1447740] [10.1021/jm00101a017]

4. Zablocki JA, Miyano M, Rao SN, Panzer-Knodle S, Nicholson N, Feigen L..  (1992)  Potent inhibitors of platelet aggregation based upon the Arg-Gly-Asp-Phe sequence of fibrinogen. A proposal on the nature of the binding interaction between the Asp-carboxylate of RGDX mimetics and the platelet GP IIb-IIIa receptor.,  35  (26): [PMID:1479591] [10.1021/jm00104a019]

5. Bi W, Bi L, Cai J, Liu S, Peng S, Fischer NO, Tok JB, Wang G..  (2006)  Dual-acting agents that possess free radical scavenging and antithrombotic activities: design, synthesis, and evaluation of phenolic tetrahydro-beta-carboline RGD peptide conjugates.,  16  (17): [PMID:16797986] [10.1016/j.bmcl.2006.06.024]

6. Xiong Y, Zhao M, Wang C, Chang HW, Peng S..  (2007)  Improved anti-osteoporosis potency and reduced endometrial membrane hyperplasia during hormone replacement therapy with estrogen-RGD peptide conjugates.,  50  (14): [PMID:17571867] [10.1021/jm070242a]

7. Liu J, Zhang X, Zhao M, Peng S..  (2009)  Synthesis, evaluation and 3D QSAR analysis of novel estradiol-RGD octapeptide conjugates with oral anti-osteoporosis activity.,  44  (4): [PMID:19004530] [10.1016/j.ejmech.2008.09.036]

8. Hegemann JD, De Simone M, Zimmermann M, Knappe TA, Xie X, Di Leva FS, Marinelli L, Novellino E, Zahler S, Kessler H, Marahiel MA..  (2014)  Rational improvement of the affinity and selectivity of integrin binding of grafted lasso peptides.,  57  (13): [PMID:24949551] [10.1021/jm5004478]

Source

Source(1):

• Scientific Literature