(2R,3R,4S,5S,6R)-2-[(1S,4R,5R)-4-[(E,3R)-3,4-dihydroxybut-1-enyl]-3,3,5-trimethylcyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 308df51d-b382-4ac4-87d3-19225a75e112
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1S,4R,5R)-4-[(E,3R)-3,4-dihydroxybut-1-enyl]-3,3,5-trimethylcyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1CC(CC(C1C=CC(CO)O)(C)C)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H](CC([C@H]1/C=C/[C@H](CO)O)(C)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C19H34O8/c1-10-6-12(7-19(2,3)13(10)5-4-11(22)8-20)26-18-17(25)16(24)15(23)14(9-21)27-18/h4-5,10-18,20-25H,6-9H2,1-3H3/b5-4+/t10-,11-,12+,13+,14-,15-,16+,17-,18-/m1/s1
• InChI Key: UTNHBQHELZUVMJ-GFFQCQNISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₄O₈
• Molecular Weight: 390.50 g/mol
• Exact Mass: 390.22536804 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.85
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7653	76.53%
Caco-2	-	0.7220	72.20%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7240	72.40%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.8866	88.66%
OATP1B3 inhibitior	+	0.9134	91.34%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9299	92.99%
P-glycoprotein inhibitior	-	0.8147	81.47%
P-glycoprotein substrate	-	0.8499	84.99%
CYP3A4 substrate	+	0.6367	63.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8402	84.02%
CYP3A4 inhibition	-	0.9257	92.57%
CYP2C9 inhibition	-	0.8559	85.59%
CYP2C19 inhibition	-	0.8677	86.77%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	-	0.7259	72.59%
CYP inhibitory promiscuity	-	0.9320	93.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6785	67.85%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9713	97.13%
Skin irritation	-	0.8430	84.30%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4494	44.94%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8514	85.14%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7760	77.60%
Acute Oral Toxicity (c)	III	0.6478	64.78%
Estrogen receptor binding	-	0.5575	55.75%
Androgen receptor binding	-	0.6036	60.36%
Thyroid receptor binding	+	0.6810	68.10%
Glucocorticoid receptor binding	+	0.6177	61.77%
Aromatase binding	+	0.6580	65.80%
PPAR gamma	-	0.4926	49.26%
Honey bee toxicity	-	0.6091	60.91%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.6896	68.96%

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	98.15%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.63%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.87%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.10%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.51%	97.09%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	91.02%	97.34%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.83%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.79%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.71%	96.21%
CHEMBL2581	P07339	Cathepsin D	85.26%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.37%	94.45%
CHEMBL206	P03372	Estrogen receptor alpha	83.72%	97.64%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.88%	96.47%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.34%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.24%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.96%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.79%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.70%	86.92%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.00%	93.10%

Plants that contains it

• Adenopeltis serrata
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Turraeanthus mannii

Cross-Links

• PubChem: 53494101
• NPASS: NPC161875
• LOTUS: LTS0127011
• wikiData: Q105278906