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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
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
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 Mon Mar 31 21:02:53 GMT 2025
Edited
by admin
on Mon Mar 31 21:02:53 GMT 2025
Record UNII
11513CCO0N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HONOKIOL
INCI   MI  
INCI  
Official Name English
FMLT BSASM H
Preferred 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
(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 Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
Code System Code Type Description
WIKIPEDIA
HONOKIOL
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
EVMPD
SUB33674
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
PUBCHEM
72303
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
DAILYMED
11513CCO0N
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
NSC
293100
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
SMS_ID
100000127617
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
FDA UNII
11513CCO0N
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID30188845
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
CAS
35354-74-6
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
RXCUI
2562546
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
MERCK INDEX
m6051
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY Merck Index
MESH
C005499
Created by admin on Mon Mar 31 21:02:53 GMT 2025 , Edited by admin on Mon Mar 31 21:02:53 GMT 2025
PRIMARY
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ACTIVE MOIETY