(S)-5-guanidino-2-(2-((S)-1-(3-methoxybenzamido)-3-methylbutyl)-5-methyloxazole-4-carboxamido)pentanoic acid

ID: ALA3736115

PubChem CID: 89570460

Max Phase: Preclinical

Molecular Formula: C24H34N6O6

Molecular Weight: 502.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)N[C@@H](CC(C)C)c2nc(C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)c(C)o2)c1

Standard InChI:  InChI=1S/C24H34N6O6/c1-13(2)11-18(29-20(31)15-7-5-8-16(12-15)35-4)22-30-19(14(3)36-22)21(32)28-17(23(33)34)9-6-10-27-24(25)26/h5,7-8,12-13,17-18H,6,9-11H2,1-4H3,(H,28,32)(H,29,31)(H,33,34)(H4,25,26,27)/t17-,18-/m0/s1

Standard InChI Key:  HXXFRBRLJLGXNV-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
    4.6332   -7.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5122   -8.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051   -8.6063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8856   -9.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3785   -9.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2589  -10.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7519  -10.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6323  -11.9449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1252  -11.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6152  -10.6957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8292  -12.7629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222   -9.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -6.1218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959   -3.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -6.1134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -7.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2756  -11.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4933   -3.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245   -8.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5348   -3.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4891   -4.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9806  -12.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0822  -11.3185    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 21  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
 15 18  1  1
 19 14  1  0
 20 19  1  0
  1 20  2  0
 18 22  1  0
 20 23  1  0
 22 24  1  0
 22 25  1  0
 17 26  2  0
 17 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 33 34  1  0
 31 33  1  0
 21 35  2  0
 21 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3736115

   (2S)-5-(diaminomethylideneamino)-2-[[2-[(1S)-1-[(3-methoxybenzoyl)amino]-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: 502.57

Molecular Weight (Monoisotopic): 502.2540

AlogP: 1.96

#Rotatable Bonds: 13

Polar Surface Area: 192.66

Molecular Species: ZWITTERION

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.98

CX Basic pKa: 11.85

CX LogP: -0.40

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.13

Np Likeness Score: -0.51

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