(4S,7S,10S,13S)-16-(3-amino-3-oxopropyl)-4-(4-aminobutyl)-7-sec-butyl-10-((R)-1-hydroxyethyl)-13-methyl-2,5,8,11,14,17,18-heptaoxo-3,6,9,12,15,19-hexaazadocosan-22-oic acid hydrochloride

ID: ALA3354605

PubChem CID: 118720293

Max Phase: Preclinical

Molecular Formula: C30H53ClN8O11

Molecular Weight: 700.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C)[C@H](NC(=O)[C@H](CCCCN)NC(C)=O)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)NC(CCC(N)=O)C(=O)C(=O)NCCC(=O)O)[C@@H](C)O.Cl

Standard InChI:  InChI=1S/C30H52N8O11.ClH/c1-6-15(2)23(37-27(46)20(35-18(5)40)9-7-8-13-31)28(47)38-24(17(4)39)29(48)34-16(3)26(45)36-19(10-11-21(32)41)25(44)30(49)33-14-12-22(42)43;/h15-17,19-20,23-24,39H,6-14,31H2,1-5H3,(H2,32,41)(H,33,49)(H,34,48)(H,35,40)(H,36,45)(H,37,46)(H,38,47)(H,42,43);1H/t15-,16+,17-,19?,20+,23+,24+;/m1./s1

Standard InChI Key:  MYNHYOJAUVDEDU-OLUPNMBYSA-N

Molfile:  

     RDKit          2D

 50 48  0  0  0  0  0  0  0  0999 V2000
    9.3110  -10.4295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4567   -8.0372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3255   -5.9870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0126   -6.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4540   -5.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7326   -9.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1480   -9.6715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9082   -6.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997   -7.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1983   -8.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -8.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9053   -8.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -9.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954   -9.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940  -10.4827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 13 21  1  0
 28  2  2  0
 17 27  1  0
  5 13  1  0
 17 33  1  0
 28 22  1  0
 14 31  2  0
  4 11  1  0
 30 16  1  0
 11 24  1  0
 25 18  1  0
 16 23  1  0
  3 23  1  1
  8 19  2  0
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 24 32  2  0
 24 12  1  0
  5  6  2  0
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  8  5  1  0
 12 25  1  0
 17 22  1  6
  3 28  1  0
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  3  7  1  0
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  7 34  1  1
  7 35  1  0
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 11 37  1  1
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 39 40  2  0
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 30 42  1  0
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 43 45  2  0
 30 46  1  6
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
M  END

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: 700.79

Molecular Weight (Monoisotopic): 700.3756

AlogP: -3.57

#Rotatable Bonds: 24

Polar Surface Area: 318.31

Molecular Species: ZWITTERION

HBA: 11

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.94

CX Basic pKa: 25.62

CX LogP: -6.34

CX LogD: -6.34

Aromatic Rings: ┄

Heavy Atoms: 49

QED Weighted: 0.03

Np Likeness Score: 0.19

References

1. Kher SS, Penzo M, Fulle S, Finn PW, Blackman MJ, Jirgensons A..  (2014)  Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1.,  24  (18): [PMID:25129616] [10.1016/j.bmcl.2014.07.086]

Source

Source(1):

• Scientific Literature