Arctiin

Details

• Internal ID: 00648391-ef0b-4854-a518-32061369fa13
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
• SMILES (Canonical): COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)OC
• InChI: InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1
• InChI Key: XOJVHLIYNSOZOO-SWOBOCGESA-N
• Popularity: 115 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₁
• Molecular Weight: 534.60 g/mol
• Exact Mass: 534.21011190 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• 20362-31-6
• Arctigenin-4-glucoside
• Arctii
• NSC 315527
• (-)-Arctiin
• UNII-TM5RQ949K7
• CCRIS 8412
• TM5RQ949K7
• CHEBI:80793
• NSC-315527
• 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)-3-((4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl)methyl)dihydro-, (3R-trans)-
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl}oxolan-2-one
• Arctiin(NSC 315527)
• Arctium
• NSC315527
• 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-, (3R-TRANS)-
• 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(beta-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-, (3R,4R)-
• 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-(.beta.-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-, (3R-trans)-
• 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-, (3R,4R)-
• Arctiin,(S)
• MFCD00870630
• Arctii;NSC 315527;Arctigenin-4-glucoside
• ARCTIIN [INCI]
• SCHEMBL381867
• CHEMBL388452
• MEGxp0_000527
• ACon1_001261
• DTXSID20942519
• BDBM50524082
• s4738
• AKOS015895721
• Arctiin, >=95% (LC/MS-ELSD)
• AM84703
• CCG-269936
• C27-H34-O11
• NCGC00169522-01
• NCGC00169522-02
• AS-18734
• LS-69357
• C16915
• Q-100251
• Q4787606
• BRD-K02568760-001-01-7
• (3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(3-methoxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)dihydrofuran-2(3H)-one
• (3R,4R)-4-(3,4-dimethoxybenzyl)-3-(3-methoxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)benzyl)dihydrofuran-2(3H)-one
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]methyl]tetrahydrofuran-2-one
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
• 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-, (3R,4R)-
• 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-(b-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-, (3R,4R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6896	68.96%
Caco-2	-	0.8137	81.37%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7822	78.22%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7083	70.83%
P-glycoprotein inhibitior	+	0.6119	61.19%
P-glycoprotein substrate	-	0.6885	68.85%
CYP3A4 substrate	+	0.5906	59.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8578	85.78%
CYP3A4 inhibition	-	0.7181	71.81%
CYP2C9 inhibition	-	0.8497	84.97%
CYP2C19 inhibition	-	0.7668	76.68%
CYP2D6 inhibition	-	0.9116	91.16%
CYP1A2 inhibition	-	0.8585	85.85%
CYP2C8 inhibition	-	0.5845	58.45%
CYP inhibitory promiscuity	-	0.6441	64.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6598	65.98%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.8649	86.49%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8449	84.49%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8740	87.40%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7327	73.27%
Acute Oral Toxicity (c)	III	0.6858	68.58%
Estrogen receptor binding	+	0.7084	70.84%
Androgen receptor binding	+	0.6128	61.28%
Thyroid receptor binding	+	0.5247	52.47%
Glucocorticoid receptor binding	+	0.6284	62.84%
Aromatase binding	-	0.5809	58.09%
PPAR gamma	+	0.6818	68.18%
Honey bee toxicity	-	0.7754	77.54%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.9066	90.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.32%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	98.03%	83.82%
CHEMBL2581	P07339	Cathepsin D	96.82%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.31%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.07%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.07%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.97%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.35%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.33%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.02%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.01%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.85%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.29%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.01%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	85.04%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.81%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.23%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	84.21%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.62%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.20%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.85%	97.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.93%	95.50%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.48%	97.50%
CHEMBL1255126	O15151	Protein Mdm4	80.37%	90.20%

Plants that contains it

• Acacia kempeana
• Aframomum sulcatum
• Alhagi pseudalhagi subsp. persarum
• Arctium lappa
• Baillonella toxisperma
• Castanopsis cuspidata
• Centaurea arenaria
• Centaurea axillaris
• Centaurea deflexa
• Centaurea imperialis
• Centaurea nigra
• Centaurea sclerolepis
• Centaurea urvillei
• Daphne feddei
• Decaisnea fargesii
• Dendrobium crepidatum
• Dendrobium thyrsiflorum
• Diospyros buxifolia
• Forsythia koreana
• Forsythia ovata
• Forsythia suspensa
• Forsythia viridissima
• Gaillardia aestivalis
• Hymenaea courbaril
• Laburnum watereri
• Lessertia frutescens
• Montanoa guatemalensis
• Onopordum acaulon
• Onopordum illyricum
• Plectocephalus americanus
• Polygonatum stenophyllum
• Psephellus schischkinii
• Pteris biaurita subsp. fornicata
• Saussurea gossipiphora
• Saussurea laniceps
• Saussurea macrota
• Saussurea medusa
• Senecio variabilis
• Teucrium lanigerum
• Torreya nucifera
• Trachelospermum asiaticum
• Trachelospermum axillare
• Trachelospermum jasminoides

Cross-Links

• PubChem: 100528
• NPASS: NPC229882
• ChEMBL: CHEMBL388452
• LOTUS: LTS0169375
• wikiData: Q4787606