(S)-2-[(S)-2-((S)-2-Formylamino-4-methylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester

ID: ALA285518

Chembl Id: CHEMBL285518

Cas Number: 65929-03-5

PubChem CID: 122066

Max Phase: Preclinical

Molecular Formula: C22H33N3O5S

Molecular Weight: 451.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCSC)NC=O

Standard InChI:  InChI=1S/C22H33N3O5S/c1-15(2)12-18(24-20(27)17(23-14-26)10-11-31-4)21(28)25-19(22(29)30-3)13-16-8-6-5-7-9-16/h5-9,14-15,17-19H,10-13H2,1-4H3,(H,23,26)(H,24,27)(H,25,28)/t17-,18-,19-/m0/s1

Standard InChI Key:  FTDSTRQDCPIBEG-FHWLQOOXSA-N

Alternative Forms

1. Parent:

   

   ALA285518

   Formylmethionyl-leucyl-phenylalanine 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: 451.59

Molecular Weight (Monoisotopic): 451.2141

AlogP: 1.29

#Rotatable Bonds: 14

Polar Surface Area: 113.60

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.06

CX Basic pKa: ┄

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -0.16

References

1. Cavicchioni G, Vertuani G, Scatturin A, Spisani S.  (1994)  The role of peptide bond in chemotactic for-met-leu-phe-ome focused by depsipeptide analogs,  4  (13): [10.1016/S0960-894X(01)80564-3]

2. Cavicchioni G, Turchetti M, Spisani S..  (2001)  Biological activity in human neutrophils of di-tripeptides, analogues of the chemotactic fMLP.,  11  (24): [PMID:11720864] [10.1016/s0960-894x(01)00640-0]

3. Torino D, Mollica A, Pinnen F, Feliciani F, Spisani S, Lucente G..  (2009)  Novel chemotactic For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on met residue replacement by 4-amino-proline scaffold: synthesis and bioactivity.,  17  (1): [PMID:19081258] [10.1016/j.bmc.2008.11.010]

4. Cavicchioni G, Fraulini A, Falzarano S, Spisani S..  (2009)  Oligomeric formylpeptide activity on human neutrophils.,  44  (12): [PMID:19748709] [10.1016/j.ejmech.2009.08.010]

5. Borgnia MJ, Eytan GD, Assaraf YG..  (1996)  Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity.,  271  (1): [PMID:8621716] [10.1074/jbc.271.6.3163]

6. Hayashi R, Miyazaki M, Osada S, Kawasaki H, Fujita I, Hamasaki Y, Kodama H..  (2013)  A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils.,  21  (3): [PMID:23276447] [10.1016/j.bmc.2012.11.046]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database