(S)-2-[2-((R)-1-Carbamimidoyl-piperidin-3-yl)-acetylamino]-3-(4-phenylethynyl-phenyl)-propionic acid methyl ester

ID: ALA419362

Chembl Id: CHEMBL419362

PubChem CID: 5288250

Max Phase: Preclinical

Molecular Formula: C26H30N4O3

Molecular Weight: 446.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ro-264550 | CHEMBL419362|2-[3-METHYL-4-(N-METHYL-GUANIDINO)-BUTYRYLAMINO]-3-(4-PHENYLETHYNYL-PHENYL)-PROPIONIC ACID METHYL ESTER|SCHEMBL14136720|1m48|BDBM50147974|AKOS040749349|DB03453|Ro-264550|NCGC00166396-01|methyl (2S)-2-[[2-[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl]amino]-3-[4-(2-phenylethynyl)phenyl]propanoate|PD070751|NS00070927|Q27460411|Methyl N-{[(3R)-1-carbamimidoyl-3-piperidinyl]acetyl}-4-(phenylethynyl)-L-phenylalaninate|methyl N-{[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl}-4-(phenShow More⌵

Canonical SMILES:  COC(=O)[C@H](Cc1ccc(C#Cc2ccccc2)cc1)NC(=O)C[C@H]1CCCN(C(=N)N)C1

Standard InChI:  InChI=1S/C26H30N4O3/c1-33-25(32)23(29-24(31)17-22-8-5-15-30(18-22)26(27)28)16-21-13-11-20(12-14-21)10-9-19-6-3-2-4-7-19/h2-4,6-7,11-14,22-23H,5,8,15-18H2,1H3,(H3,27,28)(H,29,31)/t22-,23+/m1/s1

Standard InChI Key:  MRNGXYMKYHNMLV-PKTZIBPZSA-N

Alternative Forms

1. Parent:

   

   ALA419362

   2-[3-Methyl-4-(N-methyl-guanidino)-butyrylamino]-3-(4-phenylethynyl-phenyl)-propionic acid methyl ester

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: 446.55

Molecular Weight (Monoisotopic): 446.2318

AlogP: 2.28

#Rotatable Bonds: 6

Polar Surface Area: 108.51

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.40

CX Basic pKa: 11.87

CX LogP: 2.63

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -0.46

References

1. Raimundo BC, Oslob JD, Braisted AC, Hyde J, McDowell RS, Randal M, Waal ND, Wilkinson J, Yu CH, Arkin MR..  (2004)  Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.,  47  (12): [PMID:15163192] [10.1021/jm049967u]

2. Waal ND, Yang W, Oslob JD, Arkin MR, Hyde J, Lu W, McDowell RS, Yu CH, Raimundo BC..  (2005)  Identification of nonpeptidic small-molecule inhibitors of interleukin-2.,  15  (4): [PMID:15686897] [10.1016/j.bmcl.2004.12.045]

3. Jeon YH, Lee JY, Kim S..  (2012)  Chemical modulators working at pharmacological interface of target proteins.,  20  (6): [PMID:22227462] [10.1016/j.bmc.2011.12.016]

4. Kalsoom S, Rashid U, Shaukat A, Abdalla OM, Hussain K, Khan W, Nazir S, Mesaik MA, Zaheer-ul-Haq, Ansari FL.  (2013)  In vitro and in silico exploration of IL-2 inhibition by small drug-like molecules,  22  (12): [10.1007/s00044-013-0564-x]

5. Zheng J, Chen D, Xu J, Ding X, Wu Y, Shen HC, Tan X..  (2021)  Small molecule approaches to treat autoimmune and inflammatory diseases (Part III): Targeting cytokines and cytokine receptor complexes.,  48  [PMID:34214508] [10.1016/j.bmcl.2021.128229]

Source

Source(1):

• Scientific Literature