2-(3-Carboxy-3-hydroxy-4-{5-[hydroxy-(3-phenyl-acryloyl)-amino]-1-methoxycarbonyl-pentylcarbamoyl}-butyrylamino)-6-[hydroxy-(3-phenyl-acryloyl)-amino]-hexanoic acid methyl ester

ID: ALA303290

Chembl Id: CHEMBL303290

PubChem CID: 11814693

Max Phase: Preclinical

Molecular Formula: C38H48N4O13

Molecular Weight: 768.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](CCCCN(O)C(=O)/C=C/c1ccccc1)NC(=O)CC(O)(CC(=O)N[C@@H](CCCCN(O)C(=O)/C=C/c1ccccc1)C(=O)OC)C(=O)O

Standard InChI:  InChI=1S/C38H48N4O13/c1-54-35(47)29(17-9-11-23-41(52)33(45)21-19-27-13-5-3-6-14-27)39-31(43)25-38(51,37(49)50)26-32(44)40-30(36(48)55-2)18-10-12-24-42(53)34(46)22-20-28-15-7-4-8-16-28/h3-8,13-16,19-22,29-30,51-53H,9-12,17-18,23-26H2,1-2H3,(H,39,43)(H,40,44)(H,49,50)/b21-19+,22-20+/t29-,30-/m0/s1

Standard InChI Key:  PLSKKAXSAYSCJS-HTPZWQEUSA-N

Alternative Forms

1. Parent:

   

   ALA303290

   Nannochelin A

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: 768.82

Molecular Weight (Monoisotopic): 768.3218

AlogP: 2.10

#Rotatable Bonds: 23

Polar Surface Area: 249.41

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.58

CX Basic pKa:

CX LogP: 1.98

CX LogD: -1.40

Aromatic Rings: 2

Heavy Atoms: 55

QED Weighted: 0.03

Np Likeness Score: 0.20

References

1. Guo H, Naser SA, Ghobrial G, Phanstiel O..  (2002)  Synthesis and biological evaluation of new citrate-based siderophores as potential probes for the mechanism of iron uptake in mycobacteria.,  45  (10): [PMID:11985473] [10.1021/jm0104522]

2. Jansen R, Sood S, Mohr KI, Kunze B, Irschik H, Stadler M, Müller R..  (2014)  Nannozinones and sorazinones, unprecedented pyrazinones from myxobacteria.,  77  (11): [PMID:25397992] [10.1021/np500632c]

Source

Source(1):

• Scientific Literature