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

Details

• Internal ID: b0c79cdb-9c71-4759-aa66-0c34b887da73
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7R,7aS)-7-(acetyloxymethyl)-4-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxymethyl]-6,7-dihydroxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(CC(C2(COC(=O)C)O)O)C(=CO1)COC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=C(C=C4)O
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@H]2[C@H](C[C@@H]([C@@]2(COC(=O)C)O)O)C(=CO1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)/C=C\C4=CC=C(C=C4)O
• InChI: InChI=1S/C32H42O15/c1-4-16(2)29(40)47-30-25-21(11-23(36)32(25,41)15-44-17(3)34)19(13-42-30)14-43-31-28(27(39)26(38)22(12-33)45-31)46-24(37)10-7-18-5-8-20(35)9-6-18/h5-10,13,16,21-23,25-28,30-31,33,35-36,38-39,41H,4,11-12,14-15H2,1-3H3/b10-7-/t16-,21-,22-,23+,25-,26-,27+,28-,30+,31-,32-/m1/s1
• InChI Key: AAPLRLFRMAAIBE-UODRSKAISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₅
• Molecular Weight: 666.70 g/mol
• Exact Mass: 666.25237063 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.11
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9011	90.11%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6853	68.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7845	78.45%
OATP1B3 inhibitior	+	0.9237	92.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6462	64.62%
P-glycoprotein inhibitior	+	0.6408	64.08%
P-glycoprotein substrate	+	0.6420	64.20%
CYP3A4 substrate	+	0.6930	69.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8754	87.54%
CYP3A4 inhibition	-	0.7448	74.48%
CYP2C9 inhibition	-	0.8778	87.78%
CYP2C19 inhibition	-	0.8424	84.24%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.8521	85.21%
CYP2C8 inhibition	+	0.7419	74.19%
CYP inhibitory promiscuity	-	0.8783	87.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6320	63.20%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9233	92.33%
Skin irritation	-	0.6562	65.62%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4195	41.95%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8776	87.76%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8276	82.76%
Acute Oral Toxicity (c)	I	0.4206	42.06%
Estrogen receptor binding	+	0.7675	76.75%
Androgen receptor binding	+	0.7448	74.48%
Thyroid receptor binding	-	0.5466	54.66%
Glucocorticoid receptor binding	+	0.6136	61.36%
Aromatase binding	+	0.5359	53.59%
PPAR gamma	+	0.6651	66.51%
Honey bee toxicity	-	0.6978	69.78%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9913	99.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	98.92%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.72%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.27%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.26%	97.09%
CHEMBL2581	P07339	Cathepsin D	96.53%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.26%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	94.23%	97.21%
CHEMBL2996	Q05655	Protein kinase C delta	94.18%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.88%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.84%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.44%	96.00%
CHEMBL206	P03372	Estrogen receptor alpha	92.91%	97.64%
CHEMBL242	Q92731	Estrogen receptor beta	90.59%	98.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.55%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.03%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.75%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.03%	94.08%
CHEMBL4208	P20618	Proteasome component C5	84.76%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.47%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.37%	96.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.19%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.79%	89.62%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.48%	97.28%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.73%	93.56%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.39%	94.97%
CHEMBL3401	O75469	Pregnane X receptor	80.51%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	80.26%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.04%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.04%	95.50%

Plants that contains it

• Viburnum ayavacense

Cross-Links

• PubChem: 163190106
• LOTUS: LTS0043984
• wikiData: Q104908276