3-[(1R,2R,3S)-2-[2-[(1R,4aR,6S,8aS)-6-[(2R,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-8a-methyl-2-oxo-1,3,4,4a,5,6,7,8-octahydronaphthalen-1-yl]ethyl]-3-hydroxy-2-methylcyclopentyl]-2H-furan-5-one

Details

• Internal ID: 9396fc24-4076-4781-865a-be2da127a77c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 3-[(1R,2R,3S)-2-[2-[(1R,4aR,6S,8aS)-6-[(2R,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-8a-methyl-2-oxo-1,3,4,4a,5,6,7,8-octahydronaphthalen-1-yl]ethyl]-3-hydroxy-2-methylcyclopentyl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC(=O)C3CCC4(C(CCC4O)C5=CC(=O)OC5)C)C)OC)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CCC(=O)[C@@H]3CC[C@@]4([C@H](CC[C@@H]4O)C5=CC(=O)OC5)C)C)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C36H56O13/c1-18-33(49-34-32(43)31(42)30(41)26(16-37)48-34)25(44-4)15-29(46-18)47-21-9-11-35(2)20(14-21)5-7-24(38)23(35)10-12-36(3)22(6-8-27(36)39)19-13-28(40)45-17-19/h13,18,20-23,25-27,29-34,37,39,41-43H,5-12,14-17H2,1-4H3/t18-,20-,21+,22-,23+,25-,26-,27+,29+,30-,31+,32-,33+,34+,35+,36-/m1/s1
• InChI Key: HWLQHFSNEUZBOA-IJOJEBQMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₁₃
• Molecular Weight: 696.80 g/mol
• Exact Mass: 696.37209184 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8728	87.28%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	0.8679	86.79%
OATP1B1 inhibitior	+	0.8793	87.93%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8363	83.63%
P-glycoprotein inhibitior	+	0.7155	71.55%
P-glycoprotein substrate	+	0.7262	72.62%
CYP3A4 substrate	+	0.7304	73.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9003	90.03%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9221	92.21%
CYP2C8 inhibition	+	0.4687	46.87%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9235	92.35%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7221	72.21%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7214	72.14%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.7838	78.38%
Androgen receptor binding	+	0.7296	72.96%
Thyroid receptor binding	-	0.6679	66.79%
Glucocorticoid receptor binding	+	0.6594	65.94%
Aromatase binding	+	0.6608	66.08%
PPAR gamma	+	0.6612	66.12%
Honey bee toxicity	-	0.6160	61.60%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9314	93.14%

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	98.43%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.32%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.71%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.54%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.78%	100.00%
CHEMBL2581	P07339	Cathepsin D	93.02%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.71%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.06%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.45%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.81%	85.14%
CHEMBL1871	P10275	Androgen Receptor	85.37%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.36%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.29%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.60%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.51%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	82.72%	95.93%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.75%	97.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.29%	92.86%
CHEMBL5028	O14672	ADAM10	81.18%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.59%	94.33%

Plants that contains it

• Aconitum brevicalcaratum
• Ammodendron conollyi
• Cirsium dipsacolepis
• Cocculus diversifolius
• Crinum kirkii
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 51040390
• NPASS: NPC3946