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

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
Antifungal activity of magnolol and honokiol.
2000 Feb
Effects of the extract of the bark of Magnolia obovata and its biphenolic constituents magnolol and honokiol on histamine release from peritoneal mast cells in rats.
2001 Nov
An anxiolytic agent, dihydrohonokiol-B, inhibits ammonia-induced increases in the intracellular Cl(-) of cultured rat hippocampal neurons via GABA(c) receptors.
2001 Oct 19
Anti-platelet effect of the constituents isolated from the barks and fruits of Magnolia obovata.
2002 Jun
[Study on HPLC-FPS of cortex magnoliae officinalis].
2002 Sep
The anti-inflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production.
2003 Aug 15
Honokiol ameliorates cerebral infarction from ischemia-reperfusion injury in rats.
2003 Feb
Honokiol, a small molecular weight natural product, inhibits angiogenesis in vitro and tumor growth in vivo.
2003 Sep 12
Honokiol induces apoptosis through p53-independent pathway in human colorectal cell line RKO.
2004 Aug 1
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
Honokiol induces apoptosis via cytochrome c release and caspase activation in activated rat hepatic stellate cells in vitro.
2005 Jan
Determination of honokiol and magnolol by micro HPLC with electrochemical detection and its application to the distribution analysis in branches and leaves of Magnolia obovata.
2005 Mar
Honokiol inhibits TNF-alpha-stimulated NF-kappaB activation and NF-kappaB-regulated gene expression through suppression of IKK activation.
2005 Nov 15
Differential inhibitory effects of honokiol and magnolol on excitatory amino acid-evoked cation signals and NMDA-induced seizures.
2005 Sep
Honokiol, a small molecular weight natural product, alleviates experimental mesangial proliferative glomerulonephritis.
2006 Aug
[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
Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage.
2006 May 10
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
Analysis of magnolol and honokiol in biological fluids by capillary zone electrophoresis.
2007 Feb 23
Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells.
2007 Jan 18
Honokiol induces calpain-mediated glucose-regulated protein-94 cleavage and apoptosis in human gastric cancer cells and reduces tumor growth.
2007 Oct 31
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 Thu Jul 06 08:09:47 UTC 2023
Edited
by admin
on Thu Jul 06 08:09:47 UTC 2023
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 Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
Code System Code Type Description
WIKIPEDIA
HONOKIOL
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
EVMPD
SUB33674
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
PUBCHEM
72303
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
DAILYMED
11513CCO0N
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
NSC
293100
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
SMS_ID
100000127617
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
FDA UNII
11513CCO0N
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID30188845
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
CAS
35354-74-6
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
RXCUI
2562546
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
MERCK INDEX
M6051
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY Merck Index
MESH
C005499
Created by admin on Thu Jul 06 08:09:48 UTC 2023 , Edited by admin on Thu Jul 06 08:09:48 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT