ID: ALA3261720

Max Phase: Preclinical

Molecular Formula: C24H30O6

Molecular Weight: 414.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1c(O)cc2oc3cc(O)c(CCC(C)C)c(O)c3c(=O)c2c1CCC(C)C

Standard InChI:  InChI=1S/C24H30O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h10-13,25-27H,6-9H2,1-5H3

Standard InChI Key:  HPZRMYXEESOBKU-UHFFFAOYSA-N

Molecule Features

Natural Product: No

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: 414.50

Molecular Weight (Monoisotopic): 414.2042

AlogP: 5.25

#Rotatable Bonds: 7

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.63

CX Basic pKa:

CX LogP: 6.81

CX LogD: 6.59

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: 1.40

References

1. Fei X, Jo M, Lee B, Han SB, Lee K, Jung JK, Seo SY, Kwak YS..  (2014)  Synthesis of xanthone derivatives based on α-mangostin and their biological evaluation for anti-cancer agents.,  24  (9): [PMID:24717154] [10.1016/j.bmcl.2014.03.047]

2. Koh JJ, Lin S, Aung TT, Lim F, Zou H, Bai Y, Li J, Lin H, Pang LM, Koh WL, Salleh SM, Lakshminarayanan R, Zhou L, Qiu S, Pervushin K, Verma C, Tan DT, Cao D, Liu S, Beuerman RW..  (2015)  Amino acid modified xanthone derivatives: novel, highly promising membrane-active antimicrobials for multidrug-resistant Gram-positive bacterial infections.,  58  (2): [PMID:25474410] [10.1021/jm501285x]

3. Koh JJ, Zou H, Lin S, Lin H, Soh RT, Lim FH, Koh WL, Li J, Lakshminarayanan R, Verma C, Tan DT, Cao D, Beuerman RW, Liu S..  (2016)  Nonpeptidic Amphiphilic Xanthone Derivatives: Structure-Activity Relationship and Membrane-Targeting Properties.,  59  (1): [PMID:26681070] [10.1021/acs.jmedchem.5b01500]

4. Yang K, Nong K, Gu Q, Dong J, Wang J..  (2018)  Discovery of N-hydroxy-3-alkoxybenzamides as direct acid sphingomyelinase inhibitors using a ligand-based pharmacophore model.,  151  [PMID:29649738] [10.1016/j.ejmech.2018.03.065]

5. Skácel J, Slusher BS, Tsukamoto T..  (2021)  Small Molecule Inhibitors Targeting Biosynthesis of Ceramide, the Central Hub of the Sphingolipid Network.,  64  (1.0): [PMID:33395289] [10.1021/acs.jmedchem.0c01664]

6. Lu Y, Guan T, Wang S, Zhou C, Wang M, Wang X, Zhang K, Han X, Lin J, Tang Q, Wang C, Zhou W..  (2023)  Novel xanthone antibacterials: Semi-synthesis, biological evaluation, and the action mechanisms.,  83  [PMID:36940608] [10.1016/j.bmc.2023.117232]

Source

Source(1):

• Scientific Literature