Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H18O2 |
Molecular Weight | 266.3343 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(CC=C)C=C1C2=CC(CC=C)=C(O)C=C2
InChI
InChIKey=FVYXIJYOAGAUQK-UHFFFAOYSA-N
InChI=1S/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2
Molecular Formula | C18H18O2 |
Molecular Weight | 266.3343 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Honokiol is a biphenolic natural product isolated from the bark and leaves of Magnolia plant spp. Honokiol possesses anti-carcinogenic, anti-inflammatory, anti-oxidative, anti-angiogenic as well as the inhibitory effect on malignant transformation of papillomas to carcinomas in vitro and in vivo animal models without any appreciable toxicity. Honokiol affects multiple signaling pathways, molecular and cellular targets including nuclear factor-κB (NF-κB), STAT3, epidermal growth factor receptor (EGFR), cell survival signaling, cell cycle, cyclooxygenase and other inflammatory mediators, etc. Honokiol can permeate the blood-brain barrier and the blood-cerebrospinal fluid to increase its bioavailability in neurological tissues. Diverse studies have provided evidence on the neuroprotective effect of honokiol in the central nervous system, due to its potent antioxidant activity, and amelioration of the excitotoxicity mainly related to the blockade of glutamate receptors and reduction in neuroinflammation. Honokiol can attenuate neurotoxicity exerted by abnormally aggregated Abeta in Alzheimer's disease. Honokiol is being developed by Huons as HL tablet for the treatment of alcoholic and non-alcoholic fatty liver.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28848085 |
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Target ID: STAT3 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/27849557 |
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Target ID: GO:0006914 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate [IC50 13.8 uM] | ||||
moderate [IC50 14 uM] | ||||
moderate [Ki 32.6 uM] | ||||
no [IC50 158.1 uM] | ||||
no [IC50 97.3 uM] | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
no | |||
unlikely [Ki 1392 uM] | ||||
unlikely [Ki 1709 uM] | ||||
unlikely [Ki 262 uM] | ||||
weak [IC50 36.4 uM] | ||||
weak [IC50 50.5 uM] | ||||
weak [Ki 79.8 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/25395831/ |
weak | |||
yes [IC50 0.96 uM] | ||||
yes [IC50 2.1 uM] | ||||
yes [IC50 2.2 uM] | ||||
yes [IC50 4.1 uM] | ||||
yes [IC50 8.9 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely [Km 0.41 uM] | ||||
likely | ||||
likely | ||||
likely | ||||
likely | ||||
major [Km 1.32 uM] | ||||
major [Km 3.67 uM] | ||||
minor [Km 0.85 uM] | ||||
minor [Km 1.07 uM] | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 0.84 uM] | ||||
yes [Km 1.82 uM] | ||||
yes [Km 48 uM] | ||||
yes [Km 92.3 uM] | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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The anti-inflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production. | 2003 Aug 15 |
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The mechanism of honokiol-induced and magnolol-induced inhibition on muscle contraction and Ca2+ mobilization in rat uterus. | 2003 Oct |
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Effects of Magnolol and Honokiol on the activities of streptococcal glucosyltransferases both in solution and adsorbed on an experimental pellicle. | 2004 |
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Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
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In vitro antibacterial and anti-inflammatory effects of honokiol and magnolol against Propionibacterium sp. | 2004 Aug 2 |
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Honokiol: a potent chemotherapy candidate for human colorectal carcinoma. | 2004 Dec 1 |
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[Pharmacokinetics of honokiol in rats]. | 2004 Feb |
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Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. | 2004 Mar |
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Anti-inflammatory effects of magnolol and honokiol are mediated through inhibition of the downstream pathway of MEKK-1 in NF-kappaB activation signaling. | 2005 Apr |
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Anxiolytic agent, dihydrohonokiol-B, recovers amyloid beta protein-induced neurotoxicity in cultured rat hippocampal neurons. | 2005 Aug 12-19 |
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Novel curcumin- and emodin-related compounds identified by in silico 2D/3D conformer screening induce apoptosis in tumor cells. | 2005 Aug 5 |
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[Studies on HPLC chromatogram of phenolic constituents of Cortex Magnoliae Officinalis]. | 2005 Jul |
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Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement. | 2005 Jul 28 |
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Honokiol-induced neurite outgrowth promotion depends on activation of extracellular signal-regulated kinases (ERK1/2). | 2005 Jun 1 |
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Anti-arrhythmic effects of herbal medicine. | 2005 Mar-Apr |
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Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia. | 2005 Nov |
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Honokiol protects against carbon tetrachloride induced liver damage in the rat. | 2005 Nov |
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Honokiol inhibits TNF-alpha-stimulated NF-kappaB activation and NF-kappaB-regulated gene expression through suppression of IKK activation. | 2005 Nov 15 |
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Honokiol inhibits arterial thrombosis through endothelial cell protection and stimulation of prostacyclin. | 2005 Sep |
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[Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule]. | 2006 Dec |
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Natural health products that inhibit angiogenesis: a potential source for investigational new agents to treat cancer-Part 1. | 2006 Feb |
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Honokiol reduces oxidative stress, c-jun-NH2-terminal kinase phosphorylation and protects against glycochenodeoxycholic acid-induced apoptosis in primary cultured rat hepatocytes. | 2006 Jun |
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Facile purification of honokiol and its antiviral and cytotoxic properties. | 2006 Jun 1 |
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Determination of honokiol and magnolol in cortex Magnoliae Officinalis by capillary electrophoresis with electrochemical detection. | 2006 Jun 16 |
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Down-regulation of P-glycoprotein expression in MDR breast cancer cell MCF-7/ADR by honokiol. | 2006 Nov 18 |
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Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection. | 2006 Oct |
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Honokiol causes the p21WAF1-mediated G(1)-phase arrest of the cell cycle through inducing p38 mitogen activated protein kinase in vascular smooth muscle cells. | 2006 Oct 2 |
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Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway. | 2006 Sep |
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Honokiol, a natural plant product, inhibits the bone metastatic growth of human prostate cancer cells. | 2007 Apr 1 |
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Honokiol, a neuroprotectant against mouse cerebral ischaemia, mediated by preserving Na+, K+-ATPase activity and mitochondrial functions. | 2007 Aug |
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Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol. | 2007 Aug 15 |
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Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract. | 2007 Dec |
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Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography. | 2007 Feb 23 |
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Honokiol, a natural plant product, inhibits inflammatory signals and alleviates inflammatory arthritis. | 2007 Jul 15 |
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[Effects of the active compounds of M. officinalis on cariogenic bacteria]. | 2007 Jun |
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Magnolol and honokiol: inhibitors against mouse passive cutaneous anaphylaxis reaction and scratching behaviors. | 2007 Nov |
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Protective action of honokiol, administered orally, against oxidative stress in brain of mice challenged with NMDA. | 2007 Oct |
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Agmatine protects retinal ganglion cells from hypoxia-induced apoptosis in transformed rat retinal ganglion cell line. | 2007 Oct 2 |
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Effects of honokiol and magnolol on acute and inflammatory pain models in mice. | 2007 Sep 8 |
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Antidepressant-like effects of the mixture of honokiol and magnolol from the barks of Magnolia officinalis in stressed rodents. | 2008 Apr 1 |
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Honokiol, a constituent of oriental medicinal herb magnolia officinalis, inhibits growth of PC-3 xenografts in vivo in association with apoptosis induction. | 2008 Feb 15 |
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Anti-inflammatory effect of honokiol is mediated by PI3K/Akt pathway suppression. | 2008 Jan |
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Preparation and characterization of honokiol nanoparticles. | 2008 Jul |
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Rapid simultaneous quantification of five active constituents in rat plasma by high-performance liquid chromatography/tandem mass spectrometry after oral administration of Da-Cheng-Qi decoction. | 2008 Jul 15 |
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Enhancement of therapeutic effectiveness by combining liposomal honokiol with cisplatin in ovarian carcinoma. | 2008 Jul-Aug |
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Enhanced effects of xanthohumol plus honokiol on apoptosis in 3T3-L1 adipocytes. | 2008 Jun |
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Differential proteomic analysis of HeLa cells treated with Honokiol using a quantitative proteomic strategy. | 2008 Jun |
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Chlorogenic acid and its metabolite m-coumaric acid evoke neurite outgrowth in hippocampal neuronal cells. | 2008 Mar |
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Growth inhibitory effects of obovatol through induction of apoptotic cell death in prostate and colon cancer by blocking of NF-kappaB. | 2008 Mar 17 |
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Liposomal honokiol, a promising agent for treatment of cisplatin-resistant human ovarian cancer. | 2008 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28932090
High dose 400 mg and low dose 133.4 mg daily for 12 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25763821
Honokiol inhibited the proliferation of both glioblastoma multiforme (GBM8401) parental cells and cancer stem-like side population (SP) cells in a dose-dependent manner, the IC50 were 5.3 and 11 uM, respectively. The proportions of cancer stem-like side population (SP) in GBM8401 cells were diminished by Honokiol from 1.5 % down to 0.3 % and 0.2 % at doses of 2.5 uM and 5 uM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 17 13:05:36 UTC 2022
by
admin
on
Sat Dec 17 13:05:36 UTC 2022
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Record UNII |
11513CCO0N
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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DSLD |
2680 (Number of products:8)
Created by
admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
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Code System | Code | Type | Description | ||
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HONOKIOL
Created by
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SUB33674
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72303
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11513CCO0N
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293100
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11513CCO0N
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DTXSID30188845
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35354-74-6
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2562546
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M6051
Created by
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PRIMARY | Merck Index | ||
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C005499
Created by
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PRIMARY |