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

Details

• Internal ID: 51be40d9-84d5-416d-b03c-7fc777dcdcd5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1S,4S,5R)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,3,5-trimethylcyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1CC(CC(C1(C=CC(C)O)O)(C)C)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H](CC([C@]1(/C=C/[C@@H](C)O)O)(C)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C19H34O8/c1-10-7-12(8-18(3,4)19(10,25)6-5-11(2)21)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-6,10-17,20-25H,7-9H2,1-4H3/b6-5+/t10-,11-,12+,13-,14-,15+,16-,17-,19-/m1/s1
• InChI Key: KAZMSBSNWWWNPL-QEKTYAEASA-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): -0.70
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7377	73.77%
Caco-2	-	0.7412	74.12%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7841	78.41%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9082	90.82%
OATP1B3 inhibitior	+	0.9053	90.53%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9332	93.32%
P-glycoprotein inhibitior	-	0.8242	82.42%
P-glycoprotein substrate	-	0.7588	75.88%
CYP3A4 substrate	+	0.6071	60.71%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.8800	88.00%
CYP2C9 inhibition	-	0.7908	79.08%
CYP2C19 inhibition	-	0.8396	83.96%
CYP2D6 inhibition	-	0.9503	95.03%
CYP1A2 inhibition	-	0.8525	85.25%
CYP2C8 inhibition	-	0.8611	86.11%
CYP inhibitory promiscuity	-	0.8479	84.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6778	67.78%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9629	96.29%
Skin irritation	-	0.8555	85.55%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	-	0.6923	69.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.5266	52.66%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8486	84.86%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8074	80.74%
Acute Oral Toxicity (c)	III	0.6639	66.39%
Estrogen receptor binding	+	0.5508	55.08%
Androgen receptor binding	-	0.4903	49.03%
Thyroid receptor binding	+	0.7432	74.32%
Glucocorticoid receptor binding	+	0.6792	67.92%
Aromatase binding	+	0.6884	68.84%
PPAR gamma	-	0.5154	51.54%
Honey bee toxicity	-	0.7024	70.24%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8055	80.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.06%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.81%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.17%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.80%	97.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.98%	92.86%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.83%	96.47%
CHEMBL2996	Q05655	Protein kinase C delta	88.63%	97.79%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	86.36%	92.32%
CHEMBL1951	P21397	Monoamine oxidase A	86.12%	91.49%
CHEMBL226	P30542	Adenosine A1 receptor	84.87%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.84%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.69%	86.92%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.74%	100.00%
CHEMBL2581	P07339	Cathepsin D	82.01%	98.95%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.47%	90.08%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.37%	96.61%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.87%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.56%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.32%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.16%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	80.13%	94.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.09%	95.50%

Plants that contains it

• Beaucarnea recurvata
• Centaurea arenaria
• Cotylelobium scabriusculum
• Cratystylis conocephala
• Croton cascarilloides
• Diospyros abyssinica
• Diospyros elliptifolia
• Diospyros malabarica
• Gutenbergia cordifolia
• Laurus nobilis
• Mikania scandens
• Phyllodium pulchellum
• Scorzonera hispanica
• Trapa natans var. japonica

Cross-Links

• PubChem: 21630913
• NPASS: NPC27577
• LOTUS: LTS0189590
• wikiData: Q105138052