argadin

ID: ALA445236

Chembl Id: CHEMBL445236

Cas Number: 289665-92-5

PubChem CID: 449123

Max Phase: Preclinical

Molecular Formula: C29H42N10O9

Molecular Weight: 674.72

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Argadin | Argadin|289665-92-5|CHEMBL445236|FO 7314|1waw|1w9u|SCHEMBL141316|BDBM10854|DTXSID40332296|BDBM50089857|DB04350|NS00071705|Q654611|4-[(1S, 4R, 10S, 13S, 16S, 18R)-10-[3-[[acetamido(amino)methylidene]amino]propyl]-18-hydroxy-16-(1H-imidazol-5-ylmethyl)-3, 9, 12, 15, 20-pentaoxo-2, 8, 11, 14, 17-pentazatricyclo[15.2.1.04, 8]icosan-13-yl]butanoic acid|4-[(1S,4R,10S,13S,16S,18R)-10-[3-[[acetamido(amino)methylidene]amino]propyl]-18-hydroxy-16-(1H-imidazol-5-ylmethyl)-3,9,12,15,20-pentaoxo-2,Show More⌵

Canonical SMILES:  CC(=O)NC(=N)NCCC[C@@H]1NC(=O)[C@H](CCCC(=O)O)NC(=O)[C@H](Cc2c[nH]cn2)N2C(=O)[C@H](C[C@H]2O)NC(=O)[C@H]2CCCN2C1=O

Standard InChI:  InChI=1S/C29H42N10O9/c1-15(40)34-29(30)32-9-3-6-18-27(47)38-10-4-7-20(38)25(45)37-19-12-22(41)39(28(19)48)21(11-16-13-31-14-33-16)26(46)35-17(24(44)36-18)5-2-8-23(42)43/h13-14,17-22,41H,2-12H2,1H3,(H,31,33)(H,35,46)(H,36,44)(H,37,45)(H,42,43)(H3,30,32,34,40)/t17-,18-,19-,20+,21-,22+/m0/s1

Standard InChI Key:  FOZYKTUSOWWQGR-KNPYFFGGSA-N

Alternative Forms

1. Parent:

   

   ALA445236

   ARGADIN

Molecule Features

Natural Product: Yes

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: 674.72

Molecular Weight (Monoisotopic): 674.3136

AlogP: -2.97

#Rotatable Bonds: 10

Polar Surface Area: 279.11

Molecular Species: ZWITTERION

HBA: 10

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.92

CX Basic pKa: 8.67

CX LogP: -5.86

CX LogD: -5.84

Aromatic Rings: 1

Heavy Atoms: 48

QED Weighted: 0.07

Np Likeness Score: 0.68

References

1. Gouda H, Yanai Y, Sugawara A, Sunazuka T, Omura S, Hirono S..  (2008)  Computational analysis of the binding affinities of the natural-product cyclopentapeptides argifin and argadin to chitinase B from Serratia marcescens.,  16  (7): [PMID:18313305] [10.1016/j.bmc.2008.02.017]

2. Sugawara A, Maita N, Gouda H, Yamamoto T, Hirose T, Kimura S, Saito Y, Nakano H, Kasai T, Nakano H, Shiomi K, Hirono S, Watanabe T, Taniguchi H, Omura S, Sunazuka T..  (2015)  Creation of Customized Bioactivity within a 14-Membered Macrolide Scaffold: Design, Synthesis, and Biological Evaluation Using a Family-18 Chitinase.,  58  (12): [PMID:26030312] [10.1021/acs.jmedchem.5b00175]

Source

Source(1):

• Scientific Literature