(2S,3R,4S,5S,6R)-2-[4-[(1S,2S,3S)-3,7-dihydroxy-2,3-bis(hydroxymethyl)-6-methoxy-2,4-dihydro-1H-naphthalen-1-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: e1142800-2d52-4f2d-9e95-6cc3231b030f
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(1S,2S,3S)-3,7-dihydroxy-2,3-bis(hydroxymethyl)-6-methoxy-2,4-dihydro-1H-naphthalen-1-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=C2C(C(C(CC2=C1)(CO)O)CO)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2[C@@H]([C@H]([C@@](CC2=C1)(CO)O)CO)C3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O
• InChI: InChI=1S/C26H34O12/c1-35-18-6-13-8-26(34,11-29)15(9-27)21(14(13)7-16(18)30)12-3-4-17(19(5-12)36-2)37-25-24(33)23(32)22(31)20(10-28)38-25/h3-7,15,20-25,27-34H,8-11H2,1-2H3/t15-,20-,21+,22-,23+,24-,25-,26-/m1/s1
• InChI Key: CBHWSKLIWKFSRU-MNAFQOMLSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₂
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.20502652 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• NCGC00347812-02
• (2S,3R,4S,5S,6R)-2-[4-[(1S,2S,3S)-3,7-dihydroxy-2,3-bis(hydroxymethyl)-6-methoxy-2,4-dihydro-1H-naphthalen-1-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• beta-D-Glucopyranoside, 2-methoxy-4-[(1S,2S,3S)-1,2,3,4-tetrahydro-3,7-dihydroxy-2,3-bis(hydroxymethyl)-6-methoxy-1-naphthalenyl]phenyl
• NCGC00347812-02_C26H34O12_beta-D-Glucopyranoside, 2-methoxy-4-[(1S,2S,3S)-1,2,3,4-tetrahydro-3,7-dihydroxy-2,3-bis(hydroxymethyl)-6-methoxy-1-naphthalenyl]phenyl

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5663	56.63%
Caco-2	-	0.8403	84.03%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5530	55.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8942	89.42%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7616	76.16%
P-glycoprotein inhibitior	+	0.5732	57.32%
P-glycoprotein substrate	-	0.6163	61.63%
CYP3A4 substrate	+	0.6645	66.45%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.8982	89.82%
CYP2C9 inhibition	-	0.9249	92.49%
CYP2C19 inhibition	-	0.8115	81.15%
CYP2D6 inhibition	-	0.9187	91.87%
CYP1A2 inhibition	-	0.7751	77.51%
CYP2C8 inhibition	+	0.7001	70.01%
CYP inhibitory promiscuity	-	0.8428	84.28%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6269	62.69%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9338	93.38%
Skin irritation	-	0.8260	82.60%
Skin corrosion	-	0.9486	94.86%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8899	88.99%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7819	78.19%
Acute Oral Toxicity (c)	III	0.6367	63.67%
Estrogen receptor binding	+	0.8305	83.05%
Androgen receptor binding	+	0.5413	54.13%
Thyroid receptor binding	+	0.5695	56.95%
Glucocorticoid receptor binding	+	0.6262	62.62%
Aromatase binding	+	0.5745	57.45%
PPAR gamma	+	0.5963	59.63%
Honey bee toxicity	-	0.8070	80.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7699	76.99%

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	99.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.89%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.35%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.01%	92.94%
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.87%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.77%	95.89%
CHEMBL4208	P20618	Proteasome component C5	91.23%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.81%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.15%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.71%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.53%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.15%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.08%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.89%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.52%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.77%	97.25%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.59%	89.62%
CHEMBL249	P25103	Neurokinin 1 receptor	81.46%	99.17%

Plants that contains it

• Stereospermum cylindricum

Cross-Links

• PubChem: 45360271
• LOTUS: LTS0064164
• wikiData: Q104952376