ID: ALA510257

Max Phase: Preclinical

Molecular Formula: C28H16O14

Molecular Weight: 576.42

Molecule Type: Small molecule

Representations

Synonyms (1): Vinaxanthone
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)c1cc2c(=O)c3c(C(=O)O)c(O)c(O)cc3oc2c(C(C)=O)c1-c1coc2cc(O)c(O)c(C(=O)O)c2c1=O

Standard InChI:  InChI=1S/C28H16O14/c1-7(29)9-3-10-22(33)19-15(5-13(32)25(36)21(19)28(39)40)42-26(10)16(8(2)30)17(9)11-6-41-14-4-12(31)24(35)20(27(37)38)18(14)23(11)34/h3-6,31-32,35-36H,1-2H3,(H,37,38)(H,39,40)

Standard InChI Key:  MEYYEMQDVMMNNR-UHFFFAOYSA-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: 576.42

Molecular Weight (Monoisotopic): 576.0540

AlogP: 3.34

#Rotatable Bonds: 5

Polar Surface Area: 250.08

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.40

CX Basic pKa:

CX LogP: 2.84

CX LogD: -6.81

Aromatic Rings: 5

Heavy Atoms: 42

QED Weighted: 0.10

Np Likeness Score: 1.12

References

1. Lee JS, Cho YS, Park EJ, Kim J, Oh WK, Lee HS, Ahn JS..  (1998)  Phospholipase Cgamma1 inhibitory principles from the sarcotestas of Ginkgo biloba.,  61  (7): [PMID:9677265] [10.1021/np970367q]

2. Rezanka T, Rezanka P, Sigler K..  (2008)  A biaryl xanthone derivative having axial chirality from Penicillium vinaceum.,  71  (5): [PMID:18355033] [10.1021/np800020p]

3. Yogiara null,Mordukhova EA,Kim D,Kim WG,Hwang JK,Pan JG.  (2020)  The food-grade antimicrobial xanthorrhizol targets the enoyl-ACP reductase (FabI) in Escherichia coli.,  30  (24): [PMID:33130290] [10.1016/j.bmcl.2020.127651]

4. Rana P, Ghouse SM, Akunuri R, Madhavi YV, Chopra S, Nanduri S..  (2020)  FabI (enoyl acyl carrier protein reductase) - A potential broad spectrum therapeutic target and its inhibitors.,  208  [PMID:32883635] [10.1016/j.ejmech.2020.112757]

Source

Source(1):

• Scientific Literature