(S)-2-(2-((S)-1-(3,3-dimethylbutanamido)-3-methylbutyl)-5-methyloxazole-4-carboxamido)-5-guanidinopentanoic acid

ID: ALA3734935

PubChem CID: 117634961

Max Phase: Preclinical

Molecular Formula: C22H38N6O5

Molecular Weight: 466.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc([C@H](CC(C)C)NC(=O)CC(C)(C)C)nc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C22H38N6O5/c1-12(2)10-15(26-16(29)11-22(4,5)6)19-28-17(13(3)33-19)18(30)27-14(20(31)32)8-7-9-25-21(23)24/h12,14-15H,7-11H2,1-6H3,(H,26,29)(H,27,30)(H,31,32)(H4,23,24,25)/t14-,15-/m0/s1

Standard InChI Key:  LIILRFIVVRIGRP-GJZGRUSLSA-N

Molfile:  

     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
    0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -2.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -3.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -3.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873   -4.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8797   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7644   -5.4025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2567   -5.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7429   -4.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9641   -6.2128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470   -3.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040    3.5228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    5.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2689    5.6254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2969    3.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050   -4.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    5.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    3.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969    1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    7.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6511    7.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5729    7.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    8.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -5.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120   -4.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 22  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  2  0
  1 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 15 19  1  1
 20 14  1  0
 21 20  1  0
  1 21  2  0
 19 23  1  0
 17 24  1  0
 21 25  1  0
 23 26  1  0
 23 27  1  0
 24 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 22 32  2  0
 22 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3734935

   (2S)-5-(diaminomethylideneamino)-2-[[2-[(1S)-1-(3,3-dimethylbutanoylamino)-3-methylbutyl]-5-methyl-1,3-oxazole-4-carbonyl]amino]pentanoic 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: 466.58

Molecular Weight (Monoisotopic): 466.2904

AlogP: 2.07

#Rotatable Bonds: 12

Polar Surface Area: 183.43

Molecular Species: ZWITTERION

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.98

CX Basic pKa: 11.84

CX LogP: -0.36

CX LogD: -0.36

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: -0.44

References

1. Singh R, Reed AN, Chu P, Scully CC, Yau MK, Suen JY, Durek T, Reid RC, Fairlie DP..  (2015)  Potent complement C3a receptor agonists derived from oxazole amino acids: Structure-activity relationships.,  25  (23): [PMID:26522948] [10.1016/j.bmcl.2015.10.038]

Source

Source(1):

• Scientific Literature