[(2R,3S,4S,5R,6R)-6-[[(1S,3R,4S,4aR,8aR)-4-[2-(furan-3-yl)ethyl]-8-(hydroxymethyl)-3,4,8a-trimethyl-1,2,3,4a,5,6-hexahydronaphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: d6682368-a860-4b1a-8034-a27199db3b86
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1S,3R,4S,4aR,8aR)-4-[2-(furan-3-yl)ethyl]-8-(hydroxymethyl)-3,4,8a-trimethyl-1,2,3,4a,5,6-hexahydronaphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2(C(C1(C)CCC3=COC=C3)CCC=C2CO)C)OC4C(C(C(C(O4)COC(=O)C)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)CCC3=COC=C3)CCC=C2CO)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)C)O)O)O
• InChI: InChI=1S/C28H42O9/c1-16-12-22(37-26-25(33)24(32)23(31)20(36-26)15-35-17(2)30)28(4)19(13-29)6-5-7-21(28)27(16,3)10-8-18-9-11-34-14-18/h6,9,11,14,16,20-26,29,31-33H,5,7-8,10,12-13,15H2,1-4H3/t16-,20-,21-,22+,23-,24+,25-,26+,27+,28+/m1/s1
• InChI Key: JBBXKCPPMPIYMT-XJXCHKKXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₉
• Molecular Weight: 522.60 g/mol
• Exact Mass: 522.28288291 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7855	78.55%
Caco-2	-	0.8252	82.52%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8021	80.21%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.7544	75.44%
OATP1B3 inhibitior	+	0.8658	86.58%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9186	91.86%
P-glycoprotein inhibitior	+	0.5911	59.11%
P-glycoprotein substrate	-	0.5327	53.27%
CYP3A4 substrate	+	0.7052	70.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8652	86.52%
CYP3A4 inhibition	-	0.8919	89.19%
CYP2C9 inhibition	-	0.8953	89.53%
CYP2C19 inhibition	-	0.8741	87.41%
CYP2D6 inhibition	-	0.9245	92.45%
CYP1A2 inhibition	-	0.8405	84.05%
CYP2C8 inhibition	+	0.6816	68.16%
CYP inhibitory promiscuity	-	0.8419	84.19%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5913	59.13%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9479	94.79%
Skin irritation	-	0.5890	58.90%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6943	69.43%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6822	68.22%
skin sensitisation	-	0.9162	91.62%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6528	65.28%
Acute Oral Toxicity (c)	I	0.6282	62.82%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.6450	64.50%
Thyroid receptor binding	+	0.5400	54.00%
Glucocorticoid receptor binding	+	0.6425	64.25%
Aromatase binding	+	0.6870	68.70%
PPAR gamma	+	0.6189	61.89%
Honey bee toxicity	-	0.7673	76.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9814	98.14%

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	98.96%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.23%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.67%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.15%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.45%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	89.21%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.93%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.21%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.83%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.67%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	84.36%	92.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.62%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.59%	95.93%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.50%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.65%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.07%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.58%	94.73%

Plants that contains it

• Salvia greggii

Cross-Links

• PubChem: 163188864
• LOTUS: LTS0140285
• wikiData: Q105124224