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

Details

• Internal ID: 61bbbbf0-a931-4598-ba60-5310dcf2ccb7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2R,3R,4S,5R,6S)-4-[(3S)-4-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(Z)-2-methylbut-2-enoyl]oxybut-1-en-2-yl]-2-hydroxy-1-methyl-5-[(Z)-2-methylbut-2-enoyl]oxy-7-oxabicyclo[4.1.0]heptan-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C2C(C1O)(O2)C)OC(=O)C(=CC)C)C(=C)C(CC3C(O3)(C)C)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@@H]([C@H]([C@H]2[C@@]([C@@H]1O)(O2)C)OC(=O)/C(=C\C)/C)C(=C)[C@H](C[C@@H]3C(O3)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C30H42O9/c1-11-15(4)26(32)35-19(14-20-29(8,9)38-20)18(7)21-22(36-27(33)16(5)12-2)24(31)30(10)25(39-30)23(21)37-28(34)17(6)13-3/h11-13,19-25,31H,7,14H2,1-6,8-10H3/b15-11-,16-12-,17-13-/t19-,20+,21-,22+,23+,24+,25-,30+/m0/s1
• InChI Key: POAQTLNAYFDANM-ZPOQMKEASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₉
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.28288291 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 9
• 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	+	0.9515	95.15%
Caco-2	-	0.7268	72.68%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6656	66.56%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8584	85.84%
OATP1B3 inhibitior	+	0.8929	89.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8957	89.57%
P-glycoprotein inhibitior	+	0.8248	82.48%
P-glycoprotein substrate	-	0.5932	59.32%
CYP3A4 substrate	+	0.6236	62.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8677	86.77%
CYP3A4 inhibition	-	0.6701	67.01%
CYP2C9 inhibition	-	0.8788	87.88%
CYP2C19 inhibition	-	0.8063	80.63%
CYP2D6 inhibition	-	0.9381	93.81%
CYP1A2 inhibition	-	0.9109	91.09%
CYP2C8 inhibition	-	0.7226	72.26%
CYP inhibitory promiscuity	-	0.9499	94.99%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7959	79.59%
Carcinogenicity (trinary)	Non-required	0.5823	58.23%
Eye corrosion	-	0.9756	97.56%
Eye irritation	-	0.8790	87.90%
Skin irritation	-	0.6010	60.10%
Skin corrosion	-	0.9165	91.65%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5086	50.86%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.5318	53.18%
skin sensitisation	+	0.5104	51.04%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6732	67.32%
Acute Oral Toxicity (c)	III	0.5157	51.57%
Estrogen receptor binding	+	0.7869	78.69%
Androgen receptor binding	+	0.5613	56.13%
Thyroid receptor binding	+	0.6598	65.98%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	+	0.6378	63.78%
PPAR gamma	+	0.7317	73.17%
Honey bee toxicity	-	0.4855	48.55%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.9590	95.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.59%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.67%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.38%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.28%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.16%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.74%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	85.61%	91.19%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.90%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.80%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.98%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.67%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.03%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.03%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.26%	91.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.01%	96.90%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.18%	97.28%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.09%	100.00%

Plants that contains it

• Ligularia lankongensis

Cross-Links

• PubChem: 162882022
• LOTUS: LTS0231501
• wikiData: Q105212315