(+)-Isolariciresinol-3alpha-O-beta-D-glucopyranoside

Details

• Internal ID: b27c8cf9-93cb-42ee-94ff-9ba3a455c677
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2R,3R,4S)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=C2C(C(C(CC2=C1)COC3C(C(C(C(O3)CO)O)O)O)CO)C4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2[C@@H]([C@H]([C@@H](CC2=C1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C26H34O11/c1-34-19-6-12(3-4-17(19)29)22-15-8-18(30)20(35-2)7-13(15)5-14(16(22)9-27)11-36-26-25(33)24(32)23(31)21(10-28)37-26/h3-4,6-8,14,16,21-33H,5,9-11H2,1-2H3/t14-,16-,21+,22-,23+,24-,25+,26+/m0/s1
• InChI Key: BUQQDANPHQFSEK-QBCFYRCNSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₁
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.21011190 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• NCGC00385296-01
• (?)-Isolariciresinol 2a-O-beta-D-glucopyranoside
• (+)-Isolariciresinol-3alpha-O-beta-D-glucopyranoside
• 63358-11-2
• NCGC00385296-01_C26H34O11_[(2R,3R,4S)-6-Hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5417	54.17%
Caco-2	-	0.8468	84.68%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5963	59.63%
OATP2B1 inhibitior	-	0.8622	86.22%
OATP1B1 inhibitior	+	0.8435	84.35%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4616	46.16%
P-glycoprotein inhibitior	-	0.5999	59.99%
P-glycoprotein substrate	-	0.6706	67.06%
CYP3A4 substrate	+	0.6148	61.48%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7492	74.92%
CYP3A4 inhibition	-	0.8799	87.99%
CYP2C9 inhibition	-	0.8790	87.90%
CYP2C19 inhibition	-	0.7680	76.80%
CYP2D6 inhibition	-	0.9091	90.91%
CYP1A2 inhibition	-	0.7748	77.48%
CYP2C8 inhibition	+	0.6324	63.24%
CYP inhibitory promiscuity	-	0.6057	60.57%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6627	66.27%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.8428	84.28%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8111	81.11%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.9211	92.11%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8085	80.85%
Acute Oral Toxicity (c)	III	0.6609	66.09%
Estrogen receptor binding	+	0.7985	79.85%
Androgen receptor binding	+	0.5950	59.50%
Thyroid receptor binding	+	0.6015	60.15%
Glucocorticoid receptor binding	+	0.5492	54.92%
Aromatase binding	-	0.5057	50.57%
PPAR gamma	+	0.5563	55.63%
Honey bee toxicity	-	0.8189	81.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8329	83.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.90%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.51%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.60%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.78%	89.62%
CHEMBL2581	P07339	Cathepsin D	90.76%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.55%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.51%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.46%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.31%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.36%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.29%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.42%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.19%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.33%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.15%	94.73%
CHEMBL3438	Q05513	Protein kinase C zeta	81.85%	88.48%
CHEMBL3194	P02766	Transthyretin	80.06%	90.71%

Plants that contains it

• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Crambe tatarica
• Diospyros eriantha
• Fritillaria monantha
• Glochidion zeylanicum
• Hoffmannia strigillosa
• Humulus lupulus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Osmanthus fragrans
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Spiraea formosana
• Stenocereus griseus
• Syncarpia hillii

Cross-Links

• PubChem: 10625849
• NPASS: NPC183486
• LOTUS: LTS0083512
• wikiData: Q104946257