11-((S,E)-3-((S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanamido)-5-phenylpent-1-enylsulfonyl)-N-((S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)undecanamide

ID: ALA1241103

PubChem CID: 23643994

Max Phase: Preclinical

Molecular Formula: C40H53N5O9S

Molecular Weight: 779.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)CCCCCCCCCCS(=O)(=O)/C=C/[C@H](CCc1ccccc1)NC(=O)[C@@H](N)Cc1ccc(O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C40H53N5O9S/c41-34(26-31-18-22-37(47)36(28-31)45(51)52)40(50)43-32(19-15-29-12-8-7-9-13-29)23-25-55(53,54)24-11-6-4-2-1-3-5-10-14-38(48)44-35(39(42)49)27-30-16-20-33(46)21-17-30/h7-9,12-13,16-18,20-23,25,28,32,34-35,46-47H,1-6,10-11,14-15,19,24,26-27,41H2,(H2,42,49)(H,43,50)(H,44,48)/b25-23+/t32-,34-,35-/m0/s1

Standard InChI Key:  CSHWCGNIXJHXMY-YLJLSDLWSA-N

Molfile:  

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M  CHG  2  33   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1241103

   (E)-11-(3-(2-Amino-3-(4-hydroxy-3-nitrophenyl)propanamido)-5-phenylpent-1-enylsulfonyl)-N-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)undecanamide

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: 779.96

Molecular Weight (Monoisotopic): 779.3564

AlogP: 4.65

#Rotatable Bonds: 25

Polar Surface Area: 245.05

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.63

CX Basic pKa: 7.67

CX LogP: 4.19

CX LogD: 4.18

Aromatic Rings: 3

Heavy Atoms: 55

QED Weighted: 0.04

Np Likeness Score: 0.04

References

1. Arastu-Kapur S, Ponder EL, Fonović UP, Yeoh S, Yuan F, Fonović M, Grainger M, Phillips CI, Powers JC, Bogyo M..  (2008)  Identification of proteases that regulate erythrocyte rupture by the malaria parasite Plasmodium falciparum.,  4  (3): [PMID:18246061] [10.1038/nchembio.70]

Source

Source(1):

• Scientific Literature