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 |
|---|---|---|---|
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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 |
|---|---|---|
| Liposomal honokiol, a promising agent for treatment of cisplatin-resistant human ovarian cancer. | 2008-09 |
|
| 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. | 2008-07-15 |
|
| Preparation and characterization of honokiol nanoparticles. | 2008-07 |
|
| Enhanced effects of xanthohumol plus honokiol on apoptosis in 3T3-L1 adipocytes. | 2008-06 |
|
| Differential proteomic analysis of HeLa cells treated with Honokiol using a quantitative proteomic strategy. | 2008-06 |
|
| Antidepressant-like effects of the mixture of honokiol and magnolol from the barks of Magnolia officinalis in stressed rodents. | 2008-04-01 |
|
| Growth inhibitory effects of obovatol through induction of apoptotic cell death in prostate and colon cancer by blocking of NF-kappaB. | 2008-03-17 |
|
| Chlorogenic acid and its metabolite m-coumaric acid evoke neurite outgrowth in hippocampal neuronal cells. | 2008-03 |
|
| Shb gene knockdown increases the susceptibility of SVR endothelial tumor cells to apoptotic stimuli in vitro and in vivo. | 2008-03 |
|
| Honokiol, a constituent of oriental medicinal herb magnolia officinalis, inhibits growth of PC-3 xenografts in vivo in association with apoptosis induction. | 2008-02-15 |
|
| Preparative purification of anti-tumor derivatives of honokiol by high-speed counter-current chromatography. | 2008-01-18 |
|
| Anti-inflammatory effect of honokiol is mediated by PI3K/Akt pathway suppression. | 2008-01 |
|
| Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract. | 2007-12 |
|
| Compressed mints and chewing gum containing magnolia bark extract are effective against bacteria responsible for oral malodor. | 2007-11-14 |
|
| Magnolol and honokiol: inhibitors against mouse passive cutaneous anaphylaxis reaction and scratching behaviors. | 2007-11 |
|
| Honokiol induces calpain-mediated glucose-regulated protein-94 cleavage and apoptosis in human gastric cancer cells and reduces tumor growth. | 2007-10-31 |
|
| Liquid chromatographic determination of honokiol and magnolol in hou po (Magnolia officinalis) as the raw herb and dried aqueous extract. | 2007-10-25 |
|
| Agmatine protects retinal ganglion cells from hypoxia-induced apoptosis in transformed rat retinal ganglion cell line. | 2007-10-02 |
|
| Honokiol causes G0-G1 phase cell cycle arrest in human prostate cancer cells in association with suppression of retinoblastoma protein level/phosphorylation and inhibition of E2F1 transcriptional activity. | 2007-10 |
|
| Protective action of honokiol, administered orally, against oxidative stress in brain of mice challenged with NMDA. | 2007-10 |
|
| Enhancement of therapeutic effectiveness by combining liposomal honokiol with cisplatin in ovarian carcinoma. | 2007-09-26 |
|
| Effects of honokiol and magnolol on acute and inflammatory pain models in mice. | 2007-09-08 |
|
| Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol. | 2007-08-15 |
|
| Honokiol, a neuroprotectant against mouse cerebral ischaemia, mediated by preserving Na+, K+-ATPase activity and mitochondrial functions. | 2007-08 |
|
| Honokiol, a natural plant product, inhibits inflammatory signals and alleviates inflammatory arthritis. | 2007-07-15 |
|
| Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS. | 2007-06-15 |
|
| [Effects of the active compounds of M. officinalis on cariogenic bacteria]. | 2007-06 |
|
| Honokiol, a natural biphenyl, inhibits in vitro and in vivo growth of breast cancer through induction of apoptosis and cell cycle arrest. | 2007-06 |
|
| Honokiol induces a necrotic cell death through the mitochondrial permeability transition pore. | 2007-05-15 |
|
| Honokiol, a natural plant product, inhibits the bone metastatic growth of human prostate cancer cells. | 2007-04-01 |
|
| Analysis of magnolol and honokiol in biological fluids by capillary zone electrophoresis. | 2007-02-23 |
|
| Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography. | 2007-02-23 |
|
| Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells. | 2007-01-18 |
|
| Honokiol up-regulates prostacyclin synthease protein expression and inhibits endothelial cell apoptosis. | 2007-01-05 |
|
| [Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule]. | 2006-12 |
|
| Determination of liquiritin, naringin, hesperidin, thymol, imperatorin, honokiol, isoimperatorin, and magnolol in the traditional Chinese medicinal preparation Huoxiang-zhengqi liquid using high-performance liquid chromatography. | 2006-11 |
|
| 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. | 2006-10-02 |
|
| [Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design]. | 2006-10 |
|
| [Evaluation of antioxidant activity of Radix Linderae and other two Chinese drugs using TLC-bioautography]. | 2006-10 |
|
| Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection. | 2006-10 |
|
| Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway. | 2006-09 |
|
| Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada. | 2006-08-07 |
|
| Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis. | 2006-08 |
|
| Honokiol, a small molecular weight natural product, alleviates experimental mesangial proliferative glomerulonephritis. | 2006-08 |
|
| Determination of honokiol and magnolol in cortex Magnoliae Officinalis by capillary electrophoresis with electrochemical detection. | 2006-06-16 |
|
| Facile purification of honokiol and its antiviral and cytotoxic properties. | 2006-06-01 |
|
| Honokiol reduces oxidative stress, c-jun-NH2-terminal kinase phosphorylation and protects against glycochenodeoxycholic acid-induced apoptosis in primary cultured rat hepatocytes. | 2006-06 |
|
| Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage. | 2006-05-10 |
|
| Natural health products that inhibit angiogenesis: a potential source for investigational new agents to treat cancer-Part 1. | 2006-02 |
|
| Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. | 2004-03 |
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
Mon Mar 31 21:02:53 GMT 2025
by
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on
Mon Mar 31 21:02:53 GMT 2025
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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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Official Name | English | ||
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Preferred Name | English | ||
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| Classification Tree | Code System | Code | ||
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DSLD |
2680 (Number of products:8)
Created by
admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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HONOKIOL
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SUB33674
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72303
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11513CCO0N
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293100
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100000127617
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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
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PRIMARY | Merck Index | ||
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C005499
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| Related Record | Type | Details | ||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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