ID: ALA515742

Max Phase: Preclinical

Molecular Formula: C20H24N2O7

Molecular Weight: 404.42

Molecule Type: Small molecule

Representations

Synonyms (1): (S)-Myxochelin A
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(NCCCC[C@@H](CO)NC(=O)c1cccc(O)c1O)c1cccc(O)c1O

Standard InChI:  InChI=1S/C20H24N2O7/c23-11-12(22-20(29)14-7-4-9-16(25)18(14)27)5-1-2-10-21-19(28)13-6-3-8-15(24)17(13)26/h3-4,6-9,12,23-27H,1-2,5,10-11H2,(H,21,28)(H,22,29)/t12-/m0/s1

Standard InChI Key:  WNBVGSNESTZACV-LBPRGKRZSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 404.42

Molecular Weight (Monoisotopic): 404.1584

AlogP: 1.20

#Rotatable Bonds: 9

Polar Surface Area: 159.35

Molecular Species: NEUTRAL

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.01

CX Basic pKa:

CX LogP: 2.40

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.24

Np Likeness Score: -0.04

References

1. Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y..  (2009)  Synthesis and evaluation of myxochelin analogues as antimetastatic agents.,  17  (7): [PMID:19282185] [10.1016/j.bmc.2009.02.040]

2. 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