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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

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

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
The anti-inflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production.
2003 Aug 15
The mechanism of honokiol-induced and magnolol-induced inhibition on muscle contraction and Ca2+ mobilization in rat uterus.
2003 Oct
Effects of Magnolol and Honokiol on the activities of streptococcal glucosyltransferases both in solution and adsorbed on an experimental pellicle.
2004
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004 Apr
In vitro antibacterial and anti-inflammatory effects of honokiol and magnolol against Propionibacterium sp.
2004 Aug 2
Honokiol: a potent chemotherapy candidate for human colorectal carcinoma.
2004 Dec 1
[Pharmacokinetics of honokiol in rats].
2004 Feb
Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis.
2004 Mar
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
Anxiolytic agent, dihydrohonokiol-B, recovers amyloid beta protein-induced neurotoxicity in cultured rat hippocampal neurons.
2005 Aug 12-19
Novel curcumin- and emodin-related compounds identified by in silico 2D/3D conformer screening induce apoptosis in tumor cells.
2005 Aug 5
[Studies on HPLC chromatogram of phenolic constituents of Cortex Magnoliae Officinalis].
2005 Jul
Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement.
2005 Jul 28
Honokiol-induced neurite outgrowth promotion depends on activation of extracellular signal-regulated kinases (ERK1/2).
2005 Jun 1
Anti-arrhythmic effects of herbal medicine.
2005 Mar-Apr
Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia.
2005 Nov
Honokiol protects against carbon tetrachloride induced liver damage in the rat.
2005 Nov
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
[Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule].
2006 Dec
Natural health products that inhibit angiogenesis: a potential source for investigational new agents to treat cancer-Part 1.
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
Down-regulation of P-glycoprotein expression in MDR breast cancer cell MCF-7/ADR by honokiol.
2006 Nov 18
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
Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol.
2007 Aug 15
Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract.
2007 Dec
Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography.
2007 Feb 23
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
Magnolol and honokiol: inhibitors against mouse passive cutaneous anaphylaxis reaction and scratching behaviors.
2007 Nov
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
Effects of honokiol and magnolol on acute and inflammatory pain models in mice.
2007 Sep 8
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
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
Enhancement of therapeutic effectiveness by combining liposomal honokiol with cisplatin in ovarian carcinoma.
2008 Jul-Aug
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 17 13:05:36 UTC 2022
Edited
by admin
on Sat Dec 17 13:05:36 UTC 2022
Record UNII
11513CCO0N
Record Status Validated (UNII)
Record Version
  • Download
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 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
Code System Code Type Description
WIKIPEDIA
HONOKIOL
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
EVMPD
SUB33674
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
PUBCHEM
72303
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
DAILYMED
11513CCO0N
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
NSC
293100
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
FDA UNII
11513CCO0N
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
EPA CompTox
DTXSID30188845
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
CAS
35354-74-6
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
RXCUI
2562546
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY
MERCK INDEX
M6051
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY Merck Index
MESH
C005499
Created by admin on Sat Dec 17 13:05:36 UTC 2022 , Edited by admin on Sat Dec 17 13:05:36 UTC 2022
PRIMARY