[(1R,3S,4R,6R)-4-[(3S,5S)-5,6-dihydroxy-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: a9e38214-c428-4791-aa94-819fb4182d17
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3S,4R,6R)-4-[(3S,5S)-5,6-dihydroxy-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)O)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@H](C[C@@H](C(C)(C)O)O)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C25H36O8/c1-9-13(3)22(28)31-17(12-18(26)24(6,7)30)15(5)16-11-19-25(8,33-19)21(27)20(16)32-23(29)14(4)10-2/h9-10,16-20,26,30H,5,11-12H2,1-4,6-8H3/b13-9-,14-10-/t16-,17+,18+,19-,20+,25-/m1/s1
• InChI Key: PCVNWLLLIYHKJV-UJADGJLUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₈
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.24101810 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9398	93.98%
Caco-2	-	0.6926	69.26%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6718	67.18%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8857	88.57%
OATP1B3 inhibitior	+	0.9139	91.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6866	68.66%
P-glycoprotein inhibitior	+	0.6820	68.20%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	-	0.6864	68.64%
CYP2C9 inhibition	-	0.7907	79.07%
CYP2C19 inhibition	-	0.7299	72.99%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.8567	85.67%
CYP2C8 inhibition	-	0.5812	58.12%
CYP inhibitory promiscuity	-	0.9750	97.50%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.6788	67.88%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.6474	64.74%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5583	55.83%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	+	0.7158	71.58%
skin sensitisation	-	0.6137	61.37%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4736	47.36%
Acute Oral Toxicity (c)	III	0.4734	47.34%
Estrogen receptor binding	+	0.8051	80.51%
Androgen receptor binding	-	0.4936	49.36%
Thyroid receptor binding	+	0.6496	64.96%
Glucocorticoid receptor binding	+	0.7948	79.48%
Aromatase binding	+	0.6724	67.24%
PPAR gamma	+	0.6857	68.57%
Honey bee toxicity	-	0.5871	58.71%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9798	97.98%

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	98.49%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.40%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.30%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.65%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.49%	97.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.08%	92.88%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.02%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.94%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.38%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.34%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.24%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.22%	94.45%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	85.16%	80.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.01%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.14%	91.24%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.99%	96.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.33%	97.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.30%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.80%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.32%	99.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.06%	93.56%

Plants that contains it

• Ligularia cymbulifera

Cross-Links

• PubChem: 162863999
• LOTUS: LTS0217235
• wikiData: Q105206074