[(1S,4aS,7R,7aS)-7-(acetyloxymethyl)-7-hydroxy-4-[[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: d4fe3c40-5e7b-43c4-8999-99d5360a9de0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,7R,7aS)-7-(acetyloxymethyl)-7-hydroxy-4-[[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(CCC2(COC(=O)C)O)C(=CO1)COC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@H]2[C@H](CC[C@@]2(COC(=O)C)O)C(=CO1)CO[C@H]3[C@@H]([C@@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C23H36O12/c1-11(2)6-16(26)35-21-17-14(4-5-23(17,30)10-33-12(3)25)13(8-31-21)9-32-22-20(29)19(28)18(27)15(7-24)34-22/h8,11,14-15,17-22,24,27-30H,4-7,9-10H2,1-3H3/t14-,15-,17-,18-,19-,20-,21+,22-,23+/m1/s1
• InChI Key: YYQCJTVJAARIPW-VRYXWLBUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₁₂
• Molecular Weight: 504.50 g/mol
• Exact Mass: 504.22067658 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.05
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• 97941-29-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7635	76.35%
Caco-2	-	0.8323	83.23%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.7953	79.53%
OATP1B3 inhibitior	+	0.8531	85.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	-	0.8361	83.61%
P-glycoprotein inhibitior	-	0.5635	56.35%
P-glycoprotein substrate	-	0.6248	62.48%
CYP3A4 substrate	+	0.6665	66.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.9338	93.38%
CYP2C9 inhibition	-	0.8660	86.60%
CYP2C19 inhibition	-	0.9202	92.02%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.9175	91.75%
CYP2C8 inhibition	-	0.5674	56.74%
CYP inhibitory promiscuity	-	0.9543	95.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6497	64.97%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9378	93.78%
Skin irritation	-	0.5878	58.78%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.5370	53.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3747	37.47%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.9023	90.23%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6148	61.48%
Acute Oral Toxicity (c)	III	0.4907	49.07%
Estrogen receptor binding	+	0.6328	63.28%
Androgen receptor binding	+	0.6806	68.06%
Thyroid receptor binding	-	0.6958	69.58%
Glucocorticoid receptor binding	+	0.5573	55.73%
Aromatase binding	+	0.5249	52.49%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7695	76.95%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9554	95.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.59%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.17%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.50%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.26%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.84%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.10%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	89.36%	95.93%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.66%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.30%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.56%	92.50%
CHEMBL2996	Q05655	Protein kinase C delta	85.19%	97.79%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.00%	94.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.56%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.21%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.41%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.32%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.71%	86.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.84%	82.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.40%	96.00%

Plants that contains it

• Artemisia pedemontana
• Calea cuneifolia
• Dracocephalum moldavica
• Eucalyptus rubida
• Eurya japonica
• Hemionitis lemmonii
• Juniperus formosana
• Mucuna urens
• Murdannia triquetra
• Ozothamnus ferrugineus
• Phlomis nissolii
• Stephania merrillii
• Styrax japonicus
• Tanacetum balsamitoides
• Viburnum furcatum

Cross-Links

• PubChem: 101316457
• NPASS: NPC254607
• LOTUS: LTS0077615
• wikiData: Q105368856