Myxochelin B4

ID: ALA4476763

PubChem CID: 155538568

Max Phase: Preclinical

Molecular Formula: C20H25N3O5

Molecular Weight: 387.44

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H25N3O5/c21-12-13(23-20(28)15-8-5-10-17(25)18(15)26)6-3-4-11-22-19(27)14-7-1-2-9-16(14)24/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:  HJKTUTBIUUIOGM-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   29.1152   -9.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1140  -10.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8289  -11.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5453  -10.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5424   -9.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8271   -9.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2554   -9.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2523   -8.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9714   -9.8325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6843   -9.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4003   -9.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1132   -9.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8292   -9.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5422   -9.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2581   -9.8164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9711   -9.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6870   -9.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9679   -8.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6878  -10.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4029  -11.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1169  -10.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1110   -9.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3954   -9.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5390   -8.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8230   -8.1718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8245   -8.6038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3885   -8.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8225   -9.3819    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
 23 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476763

   ---

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