(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E,4S)-4-hydroxy-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol

Details

• Internal ID: 3f86f45f-6079-44bc-a897-4efcee7115c5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E,4S)-4-hydroxy-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCC(C(=CCOC1C(C(C(C(O1)COC2C(C(C(O2)CO)O)O)O)O)O)C)O)C
• SMILES (Isomeric): CC(=CC[C@@H](/C(=C/CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H](O2)CO)O)O)O)O)O)/C)O)C
• InChI: InChI=1S/C21H36O11/c1-10(2)4-5-12(23)11(3)6-7-29-20-19(28)17(26)16(25)14(32-20)9-30-21-18(27)15(24)13(8-22)31-21/h4,6,12-28H,5,7-9H2,1-3H3/b11-6+/t12-,13-,14+,15-,16+,17-,18+,19+,20+,21+/m0/s1
• InChI Key: YURWKCHIKAZLIL-GOBCCTTRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₁₁
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.22576196 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.07
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6201	62.01%
Caco-2	-	0.8867	88.67%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7819	78.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8928	89.28%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8100	81.00%
P-glycoprotein inhibitior	-	0.7821	78.21%
P-glycoprotein substrate	-	0.9065	90.65%
CYP3A4 substrate	+	0.5519	55.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8353	83.53%
CYP3A4 inhibition	-	0.9680	96.80%
CYP2C9 inhibition	-	0.8943	89.43%
CYP2C19 inhibition	-	0.8738	87.38%
CYP2D6 inhibition	-	0.9002	90.02%
CYP1A2 inhibition	-	0.8709	87.09%
CYP2C8 inhibition	-	0.8134	81.34%
CYP inhibitory promiscuity	-	0.8926	89.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7190	71.90%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9609	96.09%
Skin irritation	-	0.7990	79.90%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6596	65.96%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6916	69.16%
skin sensitisation	-	0.8735	87.35%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.4887	48.87%
Acute Oral Toxicity (c)	III	0.5732	57.32%
Estrogen receptor binding	+	0.5333	53.33%
Androgen receptor binding	-	0.6687	66.87%
Thyroid receptor binding	+	0.5615	56.15%
Glucocorticoid receptor binding	-	0.6082	60.82%
Aromatase binding	+	0.5975	59.75%
PPAR gamma	+	0.6287	62.87%
Honey bee toxicity	-	0.7776	77.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.9600	96.00%
Fish aquatic toxicity	-	0.3639	36.39%

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	95.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.14%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	89.88%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.71%	97.25%
CHEMBL2581	P07339	Cathepsin D	87.17%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.42%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.53%	94.45%

Plants that contains it

• Rhodiola rosea

Cross-Links

• PubChem: 101849417
• LOTUS: LTS0014966
• wikiData: Q105364483