(2R,3R,4S,5S,6R)-2-[[(1S,2R,4aS,5S,8aR)-5-hydroxy-4a-(hydroxymethyl)-2-(2-hydroxypropan-2-yl)-8-methyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 98bd81a3-9e4d-4c52-9cb6-aa5d86e968eb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,2R,4aS,5S,8aR)-5-hydroxy-4a-(hydroxymethyl)-2-(2-hydroxypropan-2-yl)-8-methyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1=CCC(C2(C1C(C(CC2)C(C)(C)O)OC3C(C(C(C(O3)CO)O)O)O)CO)O
• SMILES (Isomeric): CC1=CC[C@@H]([C@@]2([C@@H]1[C@@H]([C@@H](CC2)C(C)(C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O
• InChI: InChI=1S/C21H36O9/c1-10-4-5-13(24)21(9-23)7-6-11(20(2,3)28)18(14(10)21)30-19-17(27)16(26)15(25)12(8-22)29-19/h4,11-19,22-28H,5-9H2,1-3H3/t11-,12-,13+,14+,15-,16+,17-,18-,19+,21+/m1/s1
• InChI Key: AMEFGWWHFLJZDB-RTBJYZFLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₉
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.23593272 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.34
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6495	64.95%
Caco-2	-	0.8084	80.84%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9041	90.41%
OATP1B3 inhibitior	+	0.8028	80.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7799	77.99%
P-glycoprotein inhibitior	-	0.7924	79.24%
P-glycoprotein substrate	-	0.8391	83.91%
CYP3A4 substrate	+	0.6465	64.65%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9551	95.51%
CYP2C9 inhibition	-	0.8663	86.63%
CYP2C19 inhibition	-	0.8380	83.80%
CYP2D6 inhibition	-	0.9235	92.35%
CYP1A2 inhibition	-	0.8269	82.69%
CYP2C8 inhibition	-	0.5926	59.26%
CYP inhibitory promiscuity	-	0.9416	94.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7205	72.05%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9761	97.61%
Skin irritation	-	0.6915	69.15%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.8093	80.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.5324	53.24%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6726	67.26%
skin sensitisation	-	0.8592	85.92%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7806	78.06%
Acute Oral Toxicity (c)	III	0.6353	63.53%
Estrogen receptor binding	+	0.5269	52.69%
Androgen receptor binding	+	0.5886	58.86%
Thyroid receptor binding	+	0.6022	60.22%
Glucocorticoid receptor binding	+	0.5757	57.57%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.6079	60.79%
Honey bee toxicity	-	0.7753	77.53%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8516	85.16%

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	96.61%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.30%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.49%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.36%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.26%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.42%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.05%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	86.98%	94.75%
CHEMBL2581	P07339	Cathepsin D	86.09%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.30%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.13%	93.04%
CHEMBL1871	P10275	Androgen Receptor	83.50%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.47%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.72%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.41%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.23%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.11%	96.61%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.93%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.63%	90.24%

Plants that contains it

• Ageratina saltillensis
• Dictamnus dasycarpus
• Esenbeckia hartmanii
• Grewia villosa
• Salta triflora
• Salvia polystachya
• Trifolium montanum

Cross-Links

• PubChem: 101938835
• NPASS: NPC285408
• LOTUS: LTS0236449
• wikiData: Q104914570