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

Details

• Internal ID: dc8bd4ce-6c2e-47cd-90c6-b21068ae63a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,7R,7aS)-7-(acetyloxymethyl)-7-hydroxy-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]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)COC(=O)C=CC4=CC=C(C=C4)O)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)COC(=O)/C=C\C4=CC=C(C=C4)O)O)O)O
• InChI: InChI=1S/C32H42O14/c1-17(2)12-25(36)46-30-26-22(10-11-32(26,40)16-44-18(3)33)20(13-42-30)14-43-31-29(39)28(38)27(37)23(45-31)15-41-24(35)9-6-19-4-7-21(34)8-5-19/h4-9,13,17,22-23,26-31,34,37-40H,10-12,14-16H2,1-3H3/b9-6-/t22-,23-,26-,27-,28+,29-,30+,31-,32+/m1/s1
• InChI Key: USYGRXORRSAVFG-SJJBXHEASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₄
• Molecular Weight: 650.70 g/mol
• Exact Mass: 650.25745601 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.92
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 12

Synonyms

• 97995-98-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8831	88.31%
Caco-2	-	0.8760	87.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8150	81.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7987	79.87%
OATP1B3 inhibitior	+	0.8602	86.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.7040	70.40%
P-glycoprotein inhibitior	+	0.6637	66.37%
P-glycoprotein substrate	+	0.5674	56.74%
CYP3A4 substrate	+	0.7029	70.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8765	87.65%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.7977	79.77%
CYP2C19 inhibition	-	0.7949	79.49%
CYP2D6 inhibition	-	0.9025	90.25%
CYP1A2 inhibition	-	0.7939	79.39%
CYP2C8 inhibition	+	0.7138	71.38%
CYP inhibitory promiscuity	-	0.9119	91.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9264	92.64%
Skin irritation	-	0.6641	66.41%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6469	64.69%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6298	62.98%
skin sensitisation	-	0.8739	87.39%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6508	65.08%
Acute Oral Toxicity (c)	I	0.5426	54.26%
Estrogen receptor binding	+	0.7959	79.59%
Androgen receptor binding	+	0.7367	73.67%
Thyroid receptor binding	-	0.5574	55.74%
Glucocorticoid receptor binding	+	0.6898	68.98%
Aromatase binding	+	0.6170	61.70%
PPAR gamma	+	0.6898	68.98%
Honey bee toxicity	-	0.7402	74.02%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	99.08%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.34%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.43%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.47%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.01%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.27%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.93%	96.00%
CHEMBL2581	P07339	Cathepsin D	93.69%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	93.65%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.23%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.05%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.76%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.43%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.53%	89.67%
CHEMBL206	P03372	Estrogen receptor alpha	85.89%	97.64%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.73%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.63%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.62%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	85.49%	92.50%
CHEMBL221	P23219	Cyclooxygenase-1	84.66%	90.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.26%	97.21%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.82%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.99%	94.80%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.22%	97.25%
CHEMBL5028	O14672	ADAM10	81.86%	97.50%
CHEMBL242	Q92731	Estrogen receptor beta	81.49%	98.35%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.23%	85.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.93%	94.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.55%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	80.30%	94.73%

Plants that contains it

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

Cross-Links

• PubChem: 101316456
• NPASS: NPC66130
• LOTUS: LTS0162498
• wikiData: Q105278589