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

Details

• Internal ID: b983c376-844b-4560-b5a7-f4074a7c2c56
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3R,4R,6R)-4-[5-hydroxy-6-methoxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-1-methyl-2-oxo-7-oxabicyclo[4.1.0]heptan-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(CC2C(C1=O)(O2)C)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[C@@H]2[C@](C1=O)(O2)C)C(=C)C(CC(C(C)(C)OC)O)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C26H38O8/c1-10-14(3)23(29)32-18(13-19(27)25(6,7)31-9)16(5)17-12-20-26(8,34-20)22(28)21(17)33-24(30)15(4)11-2/h10-11,17-21,27H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t17-,18?,19?,20-,21-,26-/m1/s1
• InChI Key: XPBNTGONBVFRDJ-GYVCQLPKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₈
• Molecular Weight: 478.60 g/mol
• Exact Mass: 478.25666817 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9647	96.47%
Caco-2	-	0.6620	66.20%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6214	62.14%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	+	0.8802	88.02%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7792	77.92%
P-glycoprotein inhibitior	+	0.7658	76.58%
P-glycoprotein substrate	+	0.5360	53.60%
CYP3A4 substrate	+	0.6921	69.21%
CYP2C9 substrate	-	0.6145	61.45%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.6796	67.96%
CYP2C9 inhibition	-	0.8627	86.27%
CYP2C19 inhibition	-	0.7469	74.69%
CYP2D6 inhibition	-	0.9338	93.38%
CYP1A2 inhibition	-	0.8856	88.56%
CYP2C8 inhibition	-	0.5687	56.87%
CYP inhibitory promiscuity	-	0.9740	97.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8159	81.59%
Carcinogenicity (trinary)	Non-required	0.6801	68.01%
Eye corrosion	-	0.9779	97.79%
Eye irritation	-	0.8967	89.67%
Skin irritation	-	0.6321	63.21%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5853	58.53%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	+	0.6857	68.57%
skin sensitisation	-	0.5819	58.19%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5993	59.93%
Acute Oral Toxicity (c)	III	0.4717	47.17%
Estrogen receptor binding	+	0.7912	79.12%
Androgen receptor binding	+	0.5403	54.03%
Thyroid receptor binding	+	0.6587	65.87%
Glucocorticoid receptor binding	+	0.7923	79.23%
Aromatase binding	+	0.7165	71.65%
PPAR gamma	+	0.6702	67.02%
Honey bee toxicity	-	0.5628	56.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9458	94.58%

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	98.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.87%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.86%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.63%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.80%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.17%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.20%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.69%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	87.35%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.95%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.80%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.40%	89.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	84.46%	80.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.45%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.29%	99.23%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.54%	91.24%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.35%	92.29%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.19%	92.88%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.71%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.51%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.49%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.38%	96.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.01%	92.62%

Plants that contains it

• Ligularia dentata

Cross-Links

• PubChem: 102427335
• LOTUS: LTS0038416
• wikiData: Q105338134