Honokiol

Details

• Internal ID: 9101d319-d435-4c50-8459-2dfbd29bd86f
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Biphenyls and derivatives
• IUPAC Name: 2-(4-hydroxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
• SMILES (Canonical): C=CCC1=CC(=C(C=C1)O)C2=CC(=C(C=C2)O)CC=C
• SMILES (Isomeric): C=CCC1=CC(=C(C=C1)O)C2=CC(=C(C=C2)O)CC=C
• InChI: 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
• InChI Key: FVYXIJYOAGAUQK-UHFFFAOYSA-N
• Popularity: 1,488 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.30 g/mol
• Exact Mass: 266.130679813 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.22
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 35354-74-6
• 5,3'-Diallyl-2,4'-dihydroxybiphenyl
• NSC 293100
• 3,5'-Diallyl-4,2'-dihydroxybiphenyl
• C18H18O2
• Honokiol,(S)
• 3',5-diallyl-2,4'-biphenyldiol
• 3',5-Diallylbiphenyl-2,4'-diol
• CPD000387107
• CHEMBL16901
• UNII-11513CCO0N
• 2-(4-hydroxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
• CHEBI:5759
• 4-allyl-2-(3-allyl-4-hydroxy-phenyl)phenol
• 11513CCO0N
• 5,3'-Diallyl-biphenyl-2,4'-diol
• MFCD00016674
• [1,1'-Biphenyl]-2,4'-diol, 3',5-di-2-propenyl-
• NSC-293100
• 2-[4-hydroxy-3-(prop-2-en-1-yl)phenyl]-4-(prop-2-en-1-yl)phenol
• 2-(4-hydroxy-3-prop-2-enyl-phenyl)- 4-prop-2-enyl-phenol
• SMR000387107
• 3',5-di(prop-2-en-1-yl)biphenyl-2,4'-diol
• (1,1'-BIPHENYL)-2,4'-DIOL, 3',5-DI-2-PROPENYL-
• -dihydroxydiphenyl
• 3',5-diallyl-[1,1'-biphenyl]-2,4'-diol
• Honokiol, HO
• 5,3&prime
• Honokiol - 95%
• -Diallyl-2,4&prime
• FMLT BSASM H
• HONOKIOL [INCI]
• HONOKIOL [MI]
• D04DQJ
• HONOKIOL [WHO-DD]
• Honokiol, analytical standard
• cid_72303
• MLS000759481
• MLS001048916
• MLS001423980
• MLS006011755
• SCHEMBL133034
• REGID_for_CID_72303
• GTPL11610
• DTXSID30188845
• 3',1'-biphenyl)-2,4'-diol
• FVYXIJYOAGAUQK-UHFFFAOYSA-N
• HMS2051C12
• HMS2271J07
• HMS3393C12
• HMS3656G03
• (1,1'-BIPHENYL)-2,4'-DIOL, 3',5-DI-2-PROPEN-1-YL-
• AMY40657
• BCP28282
• HY-N0003
• 3',5'-Diallyl-2,4'-biphenyldiol
• AC-486
• BBL027819
• BDBM50157304
• HB0328
• NSC293100
• s2310
• STK801954
• 3'',5-diallylbiphenyl-2,4''-diol
• Honokiol, >=98% (HPLC), powder
• 3,5'-diallyl-2',4-dihydroxybiphenyl
• AKOS005622639
• 3',5-Diallyl-2,4'-dihydroxybiphenyl
• CCG-100864
• CS-1696
• NC00114
• 5,3''-Diallyl-biphenyl-2,4''-diol
• SMP2_000040
• NCGC00163567-01
• NCGC00163567-02
• NCGC00163567-03
• NCGC00163567-08
• AS-15333
• XH163752
• LS-174528
• 5,3''''-Diallyl-biphenyl-2,4''''-diol
• FT-0601638
• H1309
• SW197494-3
• EN300-7399522
• A822747
• SR-01000758208
• Q-100425
• Q5896650
• SR-01000758208-5
• {1,1'-Biphenyl]-2,4'-diol, 3,5-di-2-propenyl-
• 3'',5-di-2-propenyl-1,1''-biphenyl-2,4''-diol
• BRD-K98493452-001-01-6
• 3',5-Di-2-propen-1-yl[1,1'-biphenyl]-2,4'-diol
• Honokiol, European Pharmacopoeia (EP) Reference Standard
• Z2065671480
• [1,1'-Biphenyl]-2,4'-diol, 3',5-di-2-propen-1-yl
• 4-[2-hydroxy-5-(prop-2-en-1-yl)phenyl]-2-(prop-2-en-1-yl)phenol
• InChI=1/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,1-2,5-6H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	-	0.5252	52.52%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8313	83.13%
OATP2B1 inhibitior	-	0.7132	71.32%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.8087	80.87%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5523	55.23%
P-glycoprotein inhibitior	-	0.8741	87.41%
P-glycoprotein substrate	-	0.9280	92.80%
CYP3A4 substrate	-	0.6343	63.43%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	+	0.4276	42.76%
CYP3A4 inhibition	-	0.7856	78.56%
CYP2C9 inhibition	+	0.7918	79.18%
CYP2C19 inhibition	+	0.9142	91.42%
CYP2D6 inhibition	-	0.9043	90.43%
CYP1A2 inhibition	+	0.7059	70.59%
CYP2C8 inhibition	+	0.7228	72.28%
CYP inhibitory promiscuity	+	0.8978	89.78%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6262	62.62%
Carcinogenicity (trinary)	Non-required	0.6187	61.87%
Eye corrosion	-	0.9389	93.89%
Eye irritation	+	0.7225	72.25%
Skin irritation	-	0.6313	63.13%
Skin corrosion	-	0.8103	81.03%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4135	41.35%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	+	0.9234	92.34%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.7280	72.80%
Acute Oral Toxicity (c)	III	0.5821	58.21%
Estrogen receptor binding	+	0.8435	84.35%
Androgen receptor binding	+	0.7396	73.96%
Thyroid receptor binding	+	0.7132	71.32%
Glucocorticoid receptor binding	+	0.7950	79.50%
Aromatase binding	+	0.8394	83.94%
PPAR gamma	+	0.9427	94.27%
Honey bee toxicity	-	0.7242	72.42%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9950	99.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	4200 nM	IC50	PMID: 19481465
CHEMBL218	P21554	Cannabinoid CB1 receptor	6460 nM; 6.46 nM; 6.46 nM	Ki; Ki; Ki	PMID: 24900561; PMID: 27078864; via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	5610 nM; 5.61 nM; 5.61 nM	Ki; Ki; Ki	PMID: 24900561; PMID: 27078864; via Super-PRED
CHEMBL2392	P06746	DNA polymerase beta	35481.3 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM	Potency	via CMAUP
CHEMBL2061	P19793	Retinoid X receptor alpha	11.8 nM	ED50	PMID: 24959987

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.30%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.66%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.25%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.51%	83.57%
CHEMBL1951	P21397	Monoamine oxidase A	93.99%	91.49%
CHEMBL3194	P02766	Transthyretin	87.96%	90.71%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.34%	90.24%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.48%	96.12%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.11%	99.15%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	84.81%	88.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.05%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.63%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.59%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.47%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.99%	91.71%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.92%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	81.23%	94.73%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.03%	94.01%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.42%	96.95%

Plants that contains it

• Aconitum carmichaelii
• Aconitum japonicum
• Alpinia flabellata
• Angelica japonica
• Artemisia capillaris
• Baccharis truncata
• Benincasa hispida
• Centaurea benedicta
• Chamaecyparis formosensis
• Chloranthus fortunei
• Chuquiraga erinacea
• Cryptomeria japonica
• Cuphea hyssopifolia
• Cylindrolobus mucronatus
• Euphorbia palustris
• Euphorbia pithyusa
• Farfugium japonicum
• Fouquieria diguetii
• Fritillaria monantha
• Holarrhena floribunda
• Illicium verum
• Isodon flavidus
• Lathyrus latifolius
• Magnolia obovata
• Magnolia officinalis
• Magnolia officinalis var. biloba
• Magnolia virginiana
• Ononis viscosa
• Paragynoxys meridana
• Pedicularis rex
• Pinus edulis
• Posidonia oceanica
• Pterocarpus erinaceus
• Pyrus bourgaeana
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Salvia broussonetii
• Sandoricum koetjape
• Sedum sarmentosum
• Sorbus torminalis
• Suaeda maritima
• Taxus mairei
• Torreya nucifera
• Tripterygium wilfordii
• Triunia erythrocarpa

Cross-Links

• PubChem: 72303
• NPASS: NPC168829
• ChEMBL: CHEMBL16901
• LOTUS: LTS0033178
• wikiData: Q5896650