(2R,3R,4S,5S,6R)-2-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 17a91fd9-6036-4daf-882f-669d44d7e8a0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CC=C(C1C2)COC3C(C(C(C(O3)CO)O)O)O)C
• SMILES (Isomeric): CC1([C@H]2CC=C([C@@H]1C2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C
• InChI: InChI=1S/C16H26O6/c1-16(2)9-4-3-8(10(16)5-9)7-21-15-14(20)13(19)12(18)11(6-17)22-15/h3,9-15,17-20H,4-7H2,1-2H3/t9-,10-,11+,12+,13-,14+,15+/m0/s1
• InChI Key: ATKXBUNPUFHUHF-CLYJXRMCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₆
• Molecular Weight: 314.37 g/mol
• Exact Mass: 314.17293854 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5551	55.51%
Caco-2	-	0.7890	78.90%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7834	78.34%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8903	89.03%
OATP1B3 inhibitior	+	0.9024	90.24%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9119	91.19%
P-glycoprotein inhibitior	-	0.8872	88.72%
P-glycoprotein substrate	-	0.9055	90.55%
CYP3A4 substrate	+	0.5750	57.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8427	84.27%
CYP3A4 inhibition	-	0.9639	96.39%
CYP2C9 inhibition	-	0.8435	84.35%
CYP2C19 inhibition	-	0.7927	79.27%
CYP2D6 inhibition	-	0.9094	90.94%
CYP1A2 inhibition	-	0.8301	83.01%
CYP2C8 inhibition	-	0.7640	76.40%
CYP inhibitory promiscuity	-	0.8947	89.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6819	68.19%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9894	98.94%
Skin irritation	-	0.7859	78.59%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4540	45.40%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6947	69.47%
skin sensitisation	-	0.8292	82.92%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7013	70.13%
Acute Oral Toxicity (c)	III	0.5856	58.56%
Estrogen receptor binding	+	0.5845	58.45%
Androgen receptor binding	+	0.5228	52.28%
Thyroid receptor binding	+	0.5239	52.39%
Glucocorticoid receptor binding	+	0.5999	59.99%
Aromatase binding	-	0.5510	55.10%
PPAR gamma	+	0.5978	59.78%
Honey bee toxicity	-	0.7794	77.94%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9225	92.25%

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	97.87%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.30%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.49%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	84.00%	95.93%
CHEMBL2996	Q05655	Protein kinase C delta	83.04%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.48%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.35%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.08%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.02%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.79%	94.45%

Plants that contains it

• Rhodiola rosea

Cross-Links

• PubChem: 10734031
• LOTUS: LTS0106322
• wikiData: Q104918482