(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-2-(3-methylbut-2-enyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 17de1d84-d4b8-4c04-883a-626e8562d6dd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-2-(3-methylbut-2-enyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC(=CCC1=C(C2=CC=CC=C2C(=C1O)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=CC=CC=C2C(=C1O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C
• InChI: InChI=1S/C27H36O13/c1-11(2)7-8-14-17(30)25(40-27-23(36)21(34)19(32)16(10-29)38-27)13-6-4-3-5-12(13)24(14)39-26-22(35)20(33)18(31)15(9-28)37-26/h3-7,15-16,18-23,26-36H,8-10H2,1-2H3/t15-,16-,18-,19-,20+,21+,22-,23-,26+,27+/m1/s1
• InChI Key: CSQAGHSISJPGCD-GIKBFHJQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₃
• Molecular Weight: 568.60 g/mol
• Exact Mass: 568.21559120 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -1.59
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6850	68.50%
Caco-2	-	0.8602	86.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6388	63.88%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.7988	79.88%
OATP1B3 inhibitior	+	0.9660	96.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7561	75.61%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8959	89.59%
CYP3A4 substrate	+	0.5684	56.84%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.7886	78.86%
CYP3A4 inhibition	-	0.9457	94.57%
CYP2C9 inhibition	-	0.7616	76.16%
CYP2C19 inhibition	-	0.6392	63.92%
CYP2D6 inhibition	-	0.7556	75.56%
CYP1A2 inhibition	-	0.6294	62.94%
CYP2C8 inhibition	+	0.4470	44.70%
CYP inhibitory promiscuity	-	0.5704	57.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7184	71.84%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9030	90.30%
Skin irritation	-	0.8095	80.95%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8042	80.42%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.7291	72.91%
skin sensitisation	-	0.8245	82.45%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8613	86.13%
Acute Oral Toxicity (c)	III	0.6014	60.14%
Estrogen receptor binding	+	0.6314	63.14%
Androgen receptor binding	+	0.5746	57.46%
Thyroid receptor binding	-	0.4884	48.84%
Glucocorticoid receptor binding	+	0.5795	57.95%
Aromatase binding	+	0.5731	57.31%
PPAR gamma	+	0.6172	61.72%
Honey bee toxicity	-	0.8124	81.24%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9627	96.27%

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	99.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.32%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	94.54%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.40%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.88%	98.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.11%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.04%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.69%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.85%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.47%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.11%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.91%	95.83%

Plants that contains it

• Anisodus tanguticus
• Cardopatium corymbosum
• Indocypraea montana
• Lonchocarpus yucatanensis
• Sidastrum tehuacanum

Cross-Links

• PubChem: 16216283
• NPASS: NPC41103
• LOTUS: LTS0263406
• wikiData: Q104969496