U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of HONOKIOL

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

HIDE SMILES / InChI
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

Sources: DOI: 10.1248/cpb.20.212

Approval Year

OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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
no
no
no
no
no
no
no
no
no
no
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]
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

Drug as victim

TargetModalityActivityMetaboliteClinical 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

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Novel curcumin- and emodin-related compounds identified by in silico 2D/3D conformer screening induce apoptosis in tumor cells.
2005 Aug 5
Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement.
2005 Jul 28
Anti-arrhythmic effects of herbal medicine.
2005 Mar-Apr
Honokiol inhibits TNF-alpha-stimulated NF-kappaB activation and NF-kappaB-regulated gene expression through suppression of IKK activation.
2005 Nov 15
Honokiol inhibits arterial thrombosis through endothelial cell protection and stimulation of prostacyclin.
2005 Sep
Separation and determination of honokiol and magnolol in herbal medicines by flow injection-capillary electrophoresis.
2006 Apr
Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis.
2006 Aug
Honokiol, a small molecular weight natural product, alleviates experimental mesangial proliferative glomerulonephritis.
2006 Aug
Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada.
2006 Aug 7
[Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule].
2006 Dec
A comparative study of upright counter-current chromatography and high-performance liquid chromatograpohy for preparative isolation and purification ofphenolic compounds from Magnoliae officinalis.
2006 Feb
Honokiol reduces oxidative stress, c-jun-NH2-terminal kinase phosphorylation and protects against glycochenodeoxycholic acid-induced apoptosis in primary cultured rat hepatocytes.
2006 Jun
Facile purification of honokiol and its antiviral and cytotoxic properties.
2006 Jun 1
Determination of honokiol and magnolol in cortex Magnoliae Officinalis by capillary electrophoresis with electrochemical detection.
2006 Jun 16
Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage.
2006 May 10
Protective effects of honokiol against oxidized LDL-induced cytotoxicity and adhesion molecule expression in endothelial cells.
2006 May 15
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 Nov
[Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design].
2006 Oct
Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection.
2006 Oct
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
Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway.
2006 Sep
Honokiol, a natural plant product, inhibits the bone metastatic growth of human prostate cancer cells.
2007 Apr 1
Honokiol, a neuroprotectant against mouse cerebral ischaemia, mediated by preserving Na+, K+-ATPase activity and mitochondrial functions.
2007 Aug
Analysis of magnolol and honokiol in biological fluids by capillary zone electrophoresis.
2007 Feb 23
Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography.
2007 Feb 23
Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells.
2007 Jan 18
Honokiol, a natural plant product, inhibits inflammatory signals and alleviates inflammatory arthritis.
2007 Jul 15
[Effects of the active compounds of M. officinalis on cariogenic bacteria].
2007 Jun
Honokiol, a natural biphenyl, inhibits in vitro and in vivo growth of breast cancer through induction of apoptosis and cell cycle arrest.
2007 Jun
Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS.
2007 Jun 15
Honokiol induces a necrotic cell death through the mitochondrial permeability transition pore.
2007 May 15
Magnolol and honokiol: inhibitors against mouse passive cutaneous anaphylaxis reaction and scratching behaviors.
2007 Nov
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 Oct
Protective action of honokiol, administered orally, against oxidative stress in brain of mice challenged with NMDA.
2007 Oct
Agmatine protects retinal ganglion cells from hypoxia-induced apoptosis in transformed rat retinal ganglion cell line.
2007 Oct 2
Honokiol induces calpain-mediated glucose-regulated protein-94 cleavage and apoptosis in human gastric cancer cells and reduces tumor growth.
2007 Oct 31
Effects of honokiol and magnolol on acute and inflammatory pain models in mice.
2007 Sep 8
Liquid chromatographic determination of honokiol and magnolol in hou po (Magnolia officinalis) as the raw herb and dried aqueous extract.
2007 Sep-Oct
Antidepressant-like effects of the mixture of honokiol and magnolol from the barks of Magnolia officinalis in stressed rodents.
2008 Apr 1
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
Anti-inflammatory effect of honokiol is mediated by PI3K/Akt pathway suppression.
2008 Jan
Preparative purification of anti-tumor derivatives of honokiol by high-speed counter-current chromatography.
2008 Jan 18
Preparation and characterization of honokiol nanoparticles.
2008 Jul
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
Enhanced effects of xanthohumol plus honokiol on apoptosis in 3T3-L1 adipocytes.
2008 Jun
Differential proteomic analysis of HeLa cells treated with Honokiol using a quantitative proteomic strategy.
2008 Jun
Chlorogenic acid and its metabolite m-coumaric acid evoke neurite outgrowth in hippocampal neuronal cells.
2008 Mar
Shb gene knockdown increases the susceptibility of SVR endothelial tumor cells to apoptotic stimuli in vitro and in vivo.
2008 Mar
Growth inhibitory effects of obovatol through induction of apoptotic cell death in prostate and colon cancer by blocking of NF-kappaB.
2008 Mar 17
Liposomal honokiol, a promising agent for treatment of cisplatin-resistant human ovarian cancer.
2008 Sep
Patents

Sample Use Guides

High dose 400 mg and low dose 133.4 mg daily for 12 weeks
Route of Administration: Oral
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.
Name Type Language
HONOKIOL
INCI   MI  
INCI  
Official Name English
HONOKIOL [MI]
Common Name English
(1,1'-BIPHENYL)-2,4'-DIOL, 3',5-DI-2-PROPEN-1-YL-
Systematic Name English
3',5-DIALLYL-2,4'-BIPHENYLDIOL
Systematic Name English
NSC-293100
Code English
PURINOL
Systematic Name English
FMLT BSASM H
Brand Name English
HONOKIOL [INCI]
Common Name English
(1,1'-BIPHENYL)-2,4'-DIOL, 3',5-DI-2-PROPENYL-
Systematic Name English
Honokiol [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 2680 (Number of products:8)
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
Code System Code Type Description
WIKIPEDIA
HONOKIOL
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
EVMPD
SUB33674
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
PUBCHEM
72303
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
DAILYMED
11513CCO0N
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
NSC
293100
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
SMS_ID
100000127617
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
FDA UNII
11513CCO0N
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID30188845
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
CAS
35354-74-6
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
RXCUI
2562546
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY
MERCK INDEX
m6051
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY Merck Index
MESH
C005499
Created by admin on Sat Dec 16 01:53:28 GMT 2023 , Edited by admin on Sat Dec 16 01:53:28 GMT 2023
PRIMARY