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

ID: ALA3736513

PubChem CID: 117634967

Max Phase: Preclinical

Molecular Formula: C22H30BrN7O5

Molecular Weight: 552.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc([C@H](CC(C)C)NC(=O)c2cncc(Br)c2)nc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C22H30BrN7O5/c1-11(2)7-16(29-18(31)13-8-14(23)10-26-9-13)20-30-17(12(3)35-20)19(32)28-15(21(33)34)5-4-6-27-22(24)25/h8-11,15-16H,4-7H2,1-3H3,(H,28,32)(H,29,31)(H,33,34)(H4,24,25,27)/t15-,16-/m0/s1

Standard InChI Key:  AGTWYKXMPIDJBA-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

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    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
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   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
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    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 N   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
    0.0000    2.7000    0.0000 Br  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
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  3  4  1  0
  4 21  1  1
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  6  7  1  0
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 15 18  1  1
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  1 20  2  0
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 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
 29 33  1  0
 21 34  2  0
 21 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3736513

   (2S)-2-[[2-[(1S)-1-[(5-bromopyridine-3-carbonyl)amino]-3-methylbutyl]-5-methyl-1,3-oxazole-4-carbonyl]amino]-5-(diaminomethylideneamino)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: 552.43

Molecular Weight (Monoisotopic): 551.1492

AlogP: 2.10

#Rotatable Bonds: 12

Polar Surface Area: 196.32

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: 12.22

CX LogP: -0.69

CX LogD: -0.69

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.13

Np Likeness Score: -0.61

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