2-Hydroxy-6-tetradecyloxy-benzoic acid

ID: ALA418973

Chembl Id: CHEMBL418973

PubChem CID: 10360553

Max Phase: Preclinical

Molecular Formula: C21H34O4

Molecular Weight: 350.50

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCOc1cccc(O)c1C(=O)O

Standard InChI:  InChI=1S/C21H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-25-19-16-14-15-18(22)20(19)21(23)24/h14-16,22H,2-13,17H2,1H3,(H,23,24)

Standard InChI Key:  COUQHIRIFUVLDU-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

KAT2B Tchem Histone acetyltransferase PCAF (884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecalis (29875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LOX1.5 Probable linoleate 9S-lipoxygenase 5 (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LOX1.1 Seed lipoxygenase-1 (463 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 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

Calculated Properties

Molecular Weight: 350.50Molecular Weight (Monoisotopic): 350.2457AlogP: 6.17#Rotatable Bonds: 15
Polar Surface Area: 66.76Molecular Species: ACIDHBA: 3HBD: 2
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski): 1
CX Acidic pKa: 2.44CX Basic pKa: CX LogP: 7.59CX LogD: 4.08
Aromatic Rings: 1Heavy Atoms: 25QED Weighted: 0.37Np Likeness Score: 0.24

References

1. Kanojia RM, Murray W, Bernstein J, Fernandez J, Foleno BD, Krause H, Lawrence L, Webb G, Barrett JF..  (1999)  6-oxa isosteres of anacardic acids as potent inhibitors of bacterial histidine protein kinase (HPK)-mediated two-component regulatory systems.,  (20): [PMID:10571153] [10.1016/s0960-894x(99)00508-9]
2. Ghizzoni M, Boltjes A, Graaf Cd, Haisma HJ, Dekker FJ..  (2010)  Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative.,  18  (16): [PMID:20655754] [10.1016/j.bmc.2010.06.089]
3. Wisastra R, Ghizzoni M, Boltjes A, Haisma HJ, Dekker FJ..  (2012)  Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases.,  20  (16): [PMID:22789707] [10.1016/j.bmc.2012.06.019]
4. Wisastra R, Kok PA, Eleftheriadis N, Baumgartner MP, Camacho CJ, Haisma HJ, Dekker FJ..  (2013)  Discovery of a novel activator of 5-lipoxygenase from an anacardic acid derived compound collection.,  21  (24): [PMID:24231650] [10.1016/j.bmc.2013.10.015]
5. Malwal SR, Chen L, Hicks H, Qu F, Liu W, Shillo A, Law WX, Zhang J, Chandnani N, Han X, Zheng Y, Chen CC, Guo RT, AbdelKhalek A, Seleem MN, Oldfield E..  (2019)  Discovery of Lipophilic Bisphosphonates That Target Bacterial Cell Wall and Quinone Biosynthesis.,  62  (5): [PMID:30730737] [10.1021/acs.jmedchem.8b01878]

Source