ID: ALA3416177

Max Phase: Preclinical

Molecular Formula: C22H30O4

Molecular Weight: 358.48

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  COC1=CC(=O)C(O)=C(C/C=C(\C)CC/C=C(\C)CCC=C(C)C)C1=O

Standard InChI:  InChI=1S/C22H30O4/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-18-21(24)19(23)14-20(26-5)22(18)25/h8,10,12,14,24H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+

Standard InChI Key:  AUDYECRPXIOJSY-JTCWOHKRSA-N

Associated Targets(Human)

Arachidonate 5-lipoxygenase 6568 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Arachidonate 12-lipoxygenase 3262 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Arachidonate 15-lipoxygenase 7108 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Macrophage-expressed gene 1 protein 83 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

PC-3 62116 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HeLa 62764 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

MCF7 126967 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 358.48Molecular Weight (Monoisotopic): 358.2144AlogP: 5.29#Rotatable Bonds: 9
Polar Surface Area: 63.60Molecular Species: ACIDHBA: 4HBD: 1
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: 5.54CX Basic pKa: CX LogP: 5.03CX LogD: 3.17
Aromatic Rings: 0Heavy Atoms: 26QED Weighted: 0.45Np Likeness Score: 2.43

References

1. Filosa R, Peduto A, Schaible AM, Krauth V, Weinigel C, Barz D, Petronzi C, Bruno F, Roviezzo F, Spaziano G, D'Agostino B, De Rosa M, Werz O..  (2015)  Novel series of benzoquinones with high potency against 5-lipoxygenase in human polymorphonuclear leukocytes.,  94  [PMID:25765759] [10.1016/j.ejmech.2015.02.042]
2. Jiso A, Kittiwisut S, Chantakul R, Yuenyongsawad S, Putchakarn S, Schäberle TF, Temkitthaworn P, Ingkaninan K, Chaithirayanon K, Plubrukarn A..  (2020)  Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper.,  83  (2): [PMID:32040314] [10.1021/acs.jnatprod.9b00886]

Source