(2S,3S)-2-((S)-2-{(S)-2-[4-(4-dimethylamino-phenylazo)-benzoylamino]-5-guanidino-pentanoylamino}-5-guanidino-pentanoylamino)-3-methyl-pentanoic acid

ID: ALA446366

PubChem CID: 44454404

Max Phase: Preclinical

Molecular Formula: C33H50N12O5

Molecular Weight: 694.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)c1ccc(/N=N/c2ccc(N(C)C)cc2)cc1)C(=O)O

Standard InChI:  InChI=1S/C33H50N12O5/c1-5-20(2)27(31(49)50)42-30(48)26(9-7-19-39-33(36)37)41-29(47)25(8-6-18-38-32(34)35)40-28(46)21-10-12-22(13-11-21)43-44-23-14-16-24(17-15-23)45(3)4/h10-17,20,25-27H,5-9,18-19H2,1-4H3,(H,40,46)(H,41,47)(H,42,48)(H,49,50)(H4,34,35,38)(H4,36,37,39)/b44-43+/t20-,25-,26-,27-/m0/s1

Standard InChI Key:  BXKLSUUGSSQDPF-WYTXKKOUSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA446366

   (2S,3S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]pentanoyl]amino]pentanoyl]amino]-3-methylpentanoic 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: 694.84

Molecular Weight (Monoisotopic): 694.4027

AlogP: 1.89

#Rotatable Bonds: 20

Polar Surface Area: 276.36

Molecular Species: ZWITTERION

HBA: 9

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.97

CX Basic pKa: 12.00

CX LogP: -0.07

CX LogD: -2.01

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.04

Np Likeness Score: -0.27

References

1. Agarkov A, Chauhan S, Lory PJ, Gilbertson SR, Motin VL..  (2008)  Substrate specificity and screening of the integral membrane protease Pla.,  18  (1): [PMID:17981463] [10.1016/j.bmcl.2007.09.104]

Source

Source(1):

• Scientific Literature