ID: ALA1242095

Max Phase: Preclinical

Molecular Formula: C18H24O4

Molecular Weight: 304.39

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)c1c(O)cc(O)c(C/C=C(\C)CCC=C(C)C)c1O

Standard InChI:  InChI=1S/C18H24O4/c1-11(2)6-5-7-12(3)8-9-14-15(20)10-16(21)17(13(4)19)18(14)22/h6,8,10,20-22H,5,7,9H2,1-4H3/b12-8+

Standard InChI Key:  RCOXTTLIGHDQHU-XYOKQWHBSA-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: 304.39

Molecular Weight (Monoisotopic): 304.1675

AlogP: 4.24

#Rotatable Bonds: 6

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.80

CX Basic pKa:

CX LogP: 5.31

CX LogD: 5.16

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.54

Np Likeness Score: 2.25

References

1. Basabe P, de Román M, Marcos IS, Diez D, Blanco A, Bodero O, Mollinedo F, Sierra BG, Urones JG..  (2010)  Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation.,  45  (9): [PMID:20619940] [10.1016/j.ejmech.2010.06.025]

2. Shaari K, Suppaiah V, Wai LK, Stanslas J, Tejo BA, Israf DA, Abas F, Ismail IS, Shuaib NH, Zareen S, Lajis NH..  (2011)  Bioassay-guided identification of an anti-inflammatory prenylated acylphloroglucinol from Melicope ptelefolia and molecular insights into its interaction with 5-lipoxygenase.,  19  (21): [PMID:21958738] [10.1016/j.bmc.2011.09.001]

3. Sun Q, Schmidt S, Tremmel M, Heilmann J, König B..  (2014)  Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity.,  85  [PMID:25128665] [10.1016/j.ejmech.2014.08.017]

4. Eaton AL, Dalal S, Cassera MB, Zhao S, Kingston DG..  (2016)  Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds.,  79  (6): [PMID:27228055] [10.1021/acs.jnatprod.6b00347]

5. Svouraki A, Garscha U, Kouloura E, Pace S, Pergola C, Krauth V, Rossi A, Sautebin L, Halabalaki M, Werz O, Gaboriaud-Kolar N, Skaltsounis AL..  (2017)  Evaluation of Dual 5-Lipoxygenase/Microsomal Prostaglandin E2 Synthase-1 Inhibitory Effect of Natural and Synthetic Acronychia-Type Isoprenylated Acetophenones.,  80  (3): [PMID:28240894] [10.1021/acs.jnatprod.6b01008]

Source

Source(1):

• Scientific Literature