(2R,3R,4S,5S,6R)-2-[[(1R,3aR,4R,5R,7aS)-1-hydroxy-1-(hydroxymethyl)-7a-methyl-5-propan-2-yl-3,3a,4,5,6,7-hexahydro-2H-inden-4-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: b6a27dc5-82fe-49eb-a79c-1115a51426f5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1R,3aR,4R,5R,7aS)-1-hydroxy-1-(hydroxymethyl)-7a-methyl-5-propan-2-yl-3,3a,4,5,6,7-hexahydro-2H-inden-4-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(C)C1CCC2(C(C1COC3C(C(C(C(O3)CO)O)O)O)CCC2(CO)O)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@]2([C@@H]([C@@H]1CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CC[C@@]2(CO)O)C
• InChI: InChI=1S/C21H38O8/c1-11(2)12-4-6-20(3)14(5-7-21(20,27)10-23)13(12)9-28-19-18(26)17(25)16(24)15(8-22)29-19/h11-19,22-27H,4-10H2,1-3H3/t12-,13-,14-,15-,16-,17+,18-,19-,20+,21+/m1/s1
• InChI Key: NSBVLCNEJFYMMI-MQXSHROSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₈O₈
• Molecular Weight: 418.50 g/mol
• Exact Mass: 418.25666817 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.38
• 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	+	0.5736	57.36%
Caco-2	-	0.7745	77.45%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6481	64.81%
OATP2B1 inhibitior	-	0.7234	72.34%
OATP1B1 inhibitior	+	0.8888	88.88%
OATP1B3 inhibitior	+	0.9083	90.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6442	64.42%
P-glycoprotein inhibitior	-	0.8038	80.38%
P-glycoprotein substrate	-	0.8308	83.08%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8352	83.52%
CYP3A4 inhibition	-	0.9296	92.96%
CYP2C9 inhibition	-	0.8614	86.14%
CYP2C19 inhibition	-	0.8554	85.54%
CYP2D6 inhibition	-	0.9590	95.90%
CYP1A2 inhibition	-	0.8858	88.58%
CYP2C8 inhibition	-	0.7134	71.34%
CYP inhibitory promiscuity	-	0.9626	96.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7170	71.70%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9332	93.32%
Skin irritation	-	0.7009	70.09%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4076	40.76%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6999	69.99%
skin sensitisation	-	0.9279	92.79%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8381	83.81%
Acute Oral Toxicity (c)	I	0.5615	56.15%
Estrogen receptor binding	+	0.6394	63.94%
Androgen receptor binding	+	0.6783	67.83%
Thyroid receptor binding	+	0.6483	64.83%
Glucocorticoid receptor binding	+	0.5812	58.12%
Aromatase binding	+	0.7246	72.46%
PPAR gamma	+	0.6106	61.06%
Honey bee toxicity	-	0.7817	78.17%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
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	98.78%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.28%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.10%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.76%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	94.65%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.89%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	93.78%	89.05%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.46%	96.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.10%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.92%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.48%	94.45%
CHEMBL1871	P10275	Androgen Receptor	86.90%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.78%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.15%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.90%	95.89%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.23%	97.47%
CHEMBL237	P41145	Kappa opioid receptor	85.06%	98.10%
CHEMBL1937	Q92769	Histone deacetylase 2	84.40%	94.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.59%	96.47%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.09%	95.89%
CHEMBL259	P32245	Melanocortin receptor 4	82.94%	95.38%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	82.87%	92.32%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.36%	92.86%
CHEMBL2996	Q05655	Protein kinase C delta	81.75%	97.79%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.45%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	80.74%	90.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.71%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.36%	82.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.18%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.09%	90.08%

Plants that contains it

• Corydalis conspersa
• Dendrobium nobile
• Gynochthodes parvifolia
• Ligustrum ovalifolium
• Mespilus germanica
• Mikania luetzelburgii
• Pittosporum brevicalyx
• Sideritis grandiflora
• Solanum euacanthum
• Ungernia victoris

Cross-Links

• PubChem: 11761556
• NPASS: NPC277772
• LOTUS: LTS0274552
• wikiData: Q105184952