Myxochelin B5

ID: ALA4522098

PubChem CID: 155542837

Max Phase: Preclinical

Molecular Formula: C20H25N3O5

Molecular Weight: 387.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC[C@H](CCCCNC(=O)c1cccc(O)c1O)NC(=O)c1ccccc1O

Standard InChI:  InChI=1S/C20H25N3O5/c21-12-13(23-20(28)14-7-1-2-9-16(14)24)6-3-4-11-22-19(27)15-8-5-10-17(25)18(15)26/h1-2,5,7-10,13,24-26H,3-4,6,11-12,21H2,(H,22,27)(H,23,28)/t13-/m0/s1

Standard InChI Key:  PYWJNFUXMHHARX-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    1.8682  -17.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671  -18.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751  -18.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848  -18.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819  -17.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733  -17.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881  -17.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850  -16.2302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974  -17.4533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4035  -17.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128  -17.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8189  -17.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5282  -17.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2343  -17.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9436  -17.4373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6497  -17.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3590  -17.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6467  -16.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3597  -18.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0681  -18.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7752  -18.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7695  -17.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0605  -17.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2313  -16.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5220  -15.8083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5709  -16.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604  -17.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0537  -16.2014    0.0000 O   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
  6 26  1  0
  1 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522098

   ---

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: 387.44

Molecular Weight (Monoisotopic): 387.1794

AlogP: 1.46

#Rotatable Bonds: 9

Polar Surface Area: 144.91

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.92

CX Basic pKa: 9.28

CX LogP: 1.53

CX LogD: 1.23

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -0.14

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