Myxochelin B3

ID: ALA4555415

PubChem CID: 155557187

Max Phase: Preclinical

Molecular Formula: C20H25N3O2

Molecular Weight: 339.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC[C@H](CCCCNC(=O)c1ccccc1)NC(=O)c1ccccc1

Standard InChI:  InChI=1S/C20H25N3O2/c21-15-18(23-20(25)17-11-5-2-6-12-17)13-7-8-14-22-19(24)16-9-3-1-4-10-16/h1-6,9-12,18H,7-8,13-15,21H2,(H,22,24)(H,23,25)/t18-/m0/s1

Standard InChI Key:  FZNCHGATFBBMPY-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   16.1275   -9.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1263  -10.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8411  -10.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5575  -10.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5546   -9.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8393   -9.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2676   -9.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2645   -8.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9835   -9.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6965   -9.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4124   -9.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1254   -9.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8413   -9.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5543   -9.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2702   -9.6913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9832   -9.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6992   -9.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9800   -8.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6998  -10.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4150  -10.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1290  -10.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1232   -9.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4074   -9.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5512   -8.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8352   -8.0467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 14 24  1  1
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555415

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 339.44

Molecular Weight (Monoisotopic): 339.1947

AlogP: 2.34

#Rotatable Bonds: 9

Polar Surface Area: 84.22

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.18

CX LogP: 2.21

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.32

References

1. Sester A, Winand L, Pace S, Hiller W, Werz O, Nett M..  (2019)  Myxochelin- and Pseudochelin-Derived Lipoxygenase Inhibitors from a Genetically Engineered Myxococcus xanthus Strain.,  82  (9): [PMID:31465225] [10.1021/acs.jnatprod.9b00403]

Source

Source(1):

• Scientific Literature