[(1R,2S,3R,4R,6R)-4-hydroxy-3-[(3R,5R)-5-hydroxy-6-methoxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: fa22089f-16b1-4392-a8ef-edc2de464663
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2S,3R,4R,6R)-4-hydroxy-3-[(3R,5R)-5-hydroxy-6-methoxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C(=O)C2(C1O2)C)O)C(=C)C(CC(C(C)(C)OC)O)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@H](C(=O)[C@]2([C@@H]1O2)C)O)C(=C)[C@@H](C[C@H](C(C)(C)OC)O)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C26H38O9/c1-10-13(3)23(30)33-16(12-17(27)25(6,7)32-9)15(5)18-19(28)21(29)26(8)22(35-26)20(18)34-24(31)14(4)11-2/h10-11,16-20,22,27-28H,5,12H2,1-4,6-9H3/b13-10-,14-11-/t16-,17-,18-,19-,20+,22-,26+/m1/s1
• InChI Key: DHYQZUBULNBFRY-APRVYDDCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₉
• Molecular Weight: 494.60 g/mol
• Exact Mass: 494.25158279 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9519	95.19%
Caco-2	-	0.7306	73.06%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5783	57.83%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8490	84.90%
OATP1B3 inhibitior	+	0.9359	93.59%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7496	74.96%
P-glycoprotein inhibitior	+	0.7267	72.67%
P-glycoprotein substrate	+	0.5501	55.01%
CYP3A4 substrate	+	0.6775	67.75%
CYP2C9 substrate	-	0.6145	61.45%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.7072	70.72%
CYP2C9 inhibition	-	0.8573	85.73%
CYP2C19 inhibition	-	0.7576	75.76%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.9040	90.40%
CYP2C8 inhibition	-	0.6523	65.23%
CYP inhibitory promiscuity	-	0.9601	96.01%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8459	84.59%
Carcinogenicity (trinary)	Non-required	0.6169	61.69%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.8815	88.15%
Skin irritation	-	0.6451	64.51%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5653	56.53%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	+	0.6050	60.50%
skin sensitisation	-	0.5778	57.78%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4943	49.43%
Acute Oral Toxicity (c)	III	0.4836	48.36%
Estrogen receptor binding	+	0.7712	77.12%
Androgen receptor binding	+	0.5652	56.52%
Thyroid receptor binding	+	0.6504	65.04%
Glucocorticoid receptor binding	+	0.7462	74.62%
Aromatase binding	+	0.6467	64.67%
PPAR gamma	+	0.6458	64.58%
Honey bee toxicity	-	0.5661	56.61%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9129	91.29%

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	97.85%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.80%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.85%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.59%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.56%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.48%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.28%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.08%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.56%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.06%	96.47%
CHEMBL3401	O75469	Pregnane X receptor	85.83%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	84.75%	91.19%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.46%	90.93%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	83.28%	80.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.02%	97.28%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.31%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.69%	99.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.31%	96.90%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.15%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.91%	96.95%

Plants that contains it

• Ligularia dentata

Cross-Links

• PubChem: 163022820
• LOTUS: LTS0105950
• wikiData: Q104980998