Lariciresinol

Details

• Internal ID: ae846773-f2fa-4148-8df2-a8a485b9bf51
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,9-epoxylignans
• IUPAC Name: 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@H]2CO[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
• InChI Key: MHXCIKYXNYCMHY-AUSJPIAWSA-N
• Popularity: 405 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 88.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• (+)-Lariciresinol
• 27003-73-2
• NSC-329247
• UNII-73XCE5OZB0
• 73XCE5OZB0
• CHEBI:67246
• CHEMBL518421
• 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2S,3R,4R)-
• DTXSID30318362
• 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-vanillyl-
• 4-((2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methoxyphenol
• larici-resinol
• Lariciresinol, (+)-
• 4-[(2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methoxyphenol
• 4-[[(3R,4R,5S)-4-(hydroxymethyl)-5-(3-methoxy-4-oxidanyl-phenyl)oxolan-3-yl]methyl]-2-methoxy-phenol
• 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
• SCHEMBL121881
• DTXCID70269485
• MHXCIKYXNYCMHY-AUSJPIAWSA-N
• (2S,3R,4R)-Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-furanmethanol; (+)-Lariciresinol
• 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2R-(2alpha,3beta,4beta))-
• BDBM50335920
• NSC329247
• AKOS032948405
• (+)-Lariciresinol, >=95.0% (HPLC)
• E87137
• Q6489358
• C(O)C1C(COC1c2ccc(O)c(OC)c2)Cc3ccc(O)c(OC)c3
• (+)-4-[[(3S,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
• 3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (2S,3R,4R)-
• 4-[(2S,3R,4R)-4-(4-Hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydro-2-furanyl]-2-methoxyphenol
• 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxy-phenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl]methyl]-2-methoxy-phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9186	91.86%
Caco-2	+	0.6052	60.52%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8846	88.46%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8902	89.02%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6687	66.87%
P-glycoprotein inhibitior	+	0.6106	61.06%
P-glycoprotein substrate	-	0.8208	82.08%
CYP3A4 substrate	+	0.5487	54.87%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.4095	40.95%
CYP3A4 inhibition	+	0.6808	68.08%
CYP2C9 inhibition	+	0.6295	62.95%
CYP2C19 inhibition	+	0.7795	77.95%
CYP2D6 inhibition	-	0.8542	85.42%
CYP1A2 inhibition	+	0.5377	53.77%
CYP2C8 inhibition	+	0.7211	72.11%
CYP inhibitory promiscuity	+	0.9397	93.97%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8708	87.08%
Carcinogenicity (trinary)	Non-required	0.5707	57.07%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.8624	86.24%
Skin irritation	-	0.8326	83.26%
Skin corrosion	-	0.9571	95.71%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7714	77.14%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8188	81.88%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8609	86.09%
Acute Oral Toxicity (c)	III	0.6454	64.54%
Estrogen receptor binding	+	0.7819	78.19%
Androgen receptor binding	+	0.7147	71.47%
Thyroid receptor binding	+	0.6796	67.96%
Glucocorticoid receptor binding	+	0.6571	65.71%
Aromatase binding	-	0.5125	51.25%
PPAR gamma	-	0.5503	55.03%
Honey bee toxicity	-	0.8896	88.96%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9566	95.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	25600 nM	IC50	PMID: 21138310

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.77%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.67%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.63%	99.17%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	90.28%	85.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.49%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.36%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.08%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.26%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.87%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.72%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.86%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.00%	89.00%

Plants that contains it

• Abies pinsapo
• Ananas comosus
• Anastatica hierochuntica
• Aquilaria sinensis
• Arabidopsis thaliana
• Araucaria angustifolia
• Arum italicum
• Astragalus mongholicus
• Berberis koreana
• Brassica fruticulosa
• Callicarpa furfuracea
• Camellia sinensis
• Capsicum annuum
• Cedrus deodara
• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Cucurbita pepo
• Cycas revoluta
• Daphne feddei
• Daphne genkwa
• Daphne mezereum
• Daphne odora
• Daphne oleoides
• Daphne tangutica
• Dirca occidentalis
• Ephedra viridis
• Eucommia ulmoides
• Euterpe oleracea
• Fagraea racemosa
• Gliricidia sepium
• Gnetum montanum
• Helianthus annuus
• Hemerocallis fulva
• Hibiscus cannabinus
• Isatis tinctoria
• Leitneria floridana
• Linum album
• Linum usitatissimum
• Magnolia denudata
• Magnolia kachirachirai
• Morina chinensis
• Nierembergia aristata
• Oenothera odorata
• Perovskia atriplicifolia
• Persicaria tinctoria
• Picea jezoensis subsp. jezoensis
• Picea koraiensis
• Pinellia ternata
• Premna resinosa
• Prunus armeniaca
• Rhodiola rosea
• Rubia cordifolia
• Rubia yunnanensis
• Sambucus nigra
• Sambucus williamsii
• Saussurea medusa
• Sesamum indicum
• Stellera chamaejasme
• Styrax camporum
• Taxus baccata
• Taxus cuspidata
• Taxus mairei
• Taxus wallichiana
• Tsuga heterophylla
• Vaccinium myrtillus
• Vitex peduncularis
• Vitex trifolia subsp. litoralis
• Vitis vinifera

Cross-Links

• PubChem: 332427
• NPASS: NPC257582
• ChEMBL: CHEMBL518421
• LOTUS: LTS0010950
• wikiData: Q6489358