Myxochelin B6

ID: ALA4474339

PubChem CID: 155536830

Max Phase: Preclinical

Molecular Formula: C20H25N3O4

Molecular Weight: 371.44

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H25N3O4/c21-13-14(23-20(27)16-9-2-4-11-18(16)25)7-5-6-12-22-19(26)15-8-1-3-10-17(15)24/h1-4,8-11,14,24-25H,5-7,12-13,21H2,(H,22,26)(H,23,27)/t14-/m0/s1

Standard InChI Key:  SOFCRXWKHRVUSZ-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   15.9256  -17.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9244  -18.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6325  -18.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3421  -18.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3393  -17.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6307  -16.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0455  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0424  -15.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7547  -17.2016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4609  -16.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1701  -17.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8763  -16.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5855  -17.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2917  -16.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0009  -17.1856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7071  -16.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4163  -17.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7040  -15.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4170  -17.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1254  -18.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8326  -17.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8268  -17.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1179  -16.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2886  -15.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5794  -15.5565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1111  -15.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6282  -15.9845    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
 23 26  1  0
  6 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474339

   ---

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: 371.44

Molecular Weight (Monoisotopic): 371.1845

AlogP: 1.76

#Rotatable Bonds: 9

Polar Surface Area: 124.68

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.87

CX Basic pKa: 9.26

CX LogP: 1.82

CX LogD: 1.54

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: -0.22

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