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

Details

• Internal ID: 4737c441-eeb7-485c-879a-20d87d852a38
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3S,4R,6R)-3-acetyloxy-4-[5,6-dihydroxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(CC2C1(O2)C)C(=C)C(CC(C(C)(C)O)O)OC(=O)C(=CC)C)OC(=O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)OC1[C@H]([C@H](C[C@@H]2[C@]1(O2)C)C(=C)C(CC(C(C)(C)O)O)OC(=O)/C(=C\C)/C)OC(=O)C
• InChI: InChI=1S/C27H40O9/c1-10-14(3)24(30)34-19(13-20(29)26(7,8)32)16(5)18-12-21-27(9,36-21)23(22(18)33-17(6)28)35-25(31)15(4)11-2/h10-11,18-23,29,32H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t18-,19?,20?,21-,22+,23?,27-/m1/s1
• InChI Key: XVXHJNWLSXMTBN-CABOIKOWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₉
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.26723285 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.93
• 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	+	0.9398	93.98%
Caco-2	-	0.7227	72.27%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6718	67.18%
OATP2B1 inhibitior	-	0.7139	71.39%
OATP1B1 inhibitior	+	0.8818	88.18%
OATP1B3 inhibitior	+	0.9139	91.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8868	88.68%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	-	0.5401	54.01%
CYP3A4 substrate	+	0.6755	67.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8938	89.38%
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	-	0.5657	56.57%
CYP inhibitory promiscuity	-	0.9750	97.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.6788	67.88%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.8962	89.62%
Skin irritation	-	0.6474	64.74%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6678	66.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4734	47.34%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	+	0.6284	62.84%
skin sensitisation	-	0.6137	61.37%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5547	55.47%
Acute Oral Toxicity (c)	III	0.4734	47.34%
Estrogen receptor binding	+	0.7572	75.72%
Androgen receptor binding	+	0.5881	58.81%
Thyroid receptor binding	+	0.6448	64.48%
Glucocorticoid receptor binding	+	0.7891	78.91%
Aromatase binding	+	0.6802	68.02%
PPAR gamma	+	0.6860	68.60%
Honey bee toxicity	-	0.5549	55.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.88%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.20%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.05%	85.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.28%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.10%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.41%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	90.74%	91.19%
CHEMBL2581	P07339	Cathepsin D	90.43%	98.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.32%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.87%	91.07%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.75%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.70%	96.47%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.59%	92.88%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.18%	91.24%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.35%	96.61%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.79%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	84.20%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.05%	99.17%
CHEMBL284	P27487	Dipeptidyl peptidase IV	83.85%	95.69%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.84%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.84%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.53%	82.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.32%	97.14%
CHEMBL233	P35372	Mu opioid receptor	83.23%	97.93%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.78%	80.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.43%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.64%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.42%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.15%	95.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.13%	97.29%

Plants that contains it

• Ligularia altaica

Cross-Links

• PubChem: 46881271
• LOTUS: LTS0002773
• wikiData: Q105343233