[(1S,2R,3S,4S,5R)-5-[(3R,5S)-3,6-dihydroxy-6-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-2,4-dihydroxy-2-methyl-3-[(Z)-2-methylbut-2-enoyl]oxycyclohexyl] (2S,3S,5S)-5-ethyl-2,3-dimethyl-6-oxooxane-2-carboxylate

Details

• Internal ID: 92d34583-b839-410a-8a0a-f4995fedcc65
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2R,3S,4S,5R)-5-[(3R,5S)-3,6-dihydroxy-6-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-2,4-dihydroxy-2-methyl-3-[(Z)-2-methylbut-2-enoyl]oxycyclohexyl] (2S,3S,5S)-5-ethyl-2,3-dimethyl-6-oxooxane-2-carboxylate
• SMILES (Canonical): CCC1CC(C(OC1=O)(C)C(=O)OC2CC(C(C(C2(C)O)OC(=O)C(=CC)C)O)C(=C)C(CC(C(C)(C)O)OC(=O)C(=CC)C)O)C
• SMILES (Isomeric): CC[C@H]1C[C@@H]([C@@](OC1=O)(C)C(=O)O[C@H]2C[C@@H]([C@@H]([C@@H]([C@]2(C)O)OC(=O)/C(=C\C)/C)O)C(=C)[C@@H](C[C@@H](C(C)(C)O)OC(=O)/C(=C\C)/C)O)C
• InChI: InChI=1S/C35H54O12/c1-12-18(4)29(38)44-25(33(8,9)42)17-24(36)21(7)23-16-26(34(10,43)28(27(23)37)46-30(39)19(5)13-2)45-32(41)35(11)20(6)15-22(14-3)31(40)47-35/h12-13,20,22-28,36-37,42-43H,7,14-17H2,1-6,8-11H3/b18-12-,19-13-/t20-,22-,23+,24+,25-,26-,27-,28-,34+,35-/m0/s1
• InChI Key: QJYJTNRVSGPYNE-UQOFLSMTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₁₂
• Molecular Weight: 666.80 g/mol
• Exact Mass: 666.36152715 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9178	91.78%
Caco-2	-	0.8487	84.87%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6841	68.41%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8623	86.23%
OATP1B3 inhibitior	+	0.8847	88.47%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8024	80.24%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	+	0.6983	69.83%
CYP3A4 substrate	+	0.6969	69.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9095	90.95%
CYP3A4 inhibition	+	0.5515	55.15%
CYP2C9 inhibition	-	0.7864	78.64%
CYP2C19 inhibition	-	0.6821	68.21%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.9286	92.86%
CYP2C8 inhibition	+	0.5578	55.78%
CYP inhibitory promiscuity	-	0.8418	84.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6968	69.68%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.6298	62.98%
Skin corrosion	-	0.9295	92.95%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4752	47.52%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	+	0.5889	58.89%
skin sensitisation	-	0.7136	71.36%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4865	48.65%
Acute Oral Toxicity (c)	III	0.5578	55.78%
Estrogen receptor binding	+	0.7503	75.03%
Androgen receptor binding	+	0.6795	67.95%
Thyroid receptor binding	+	0.5404	54.04%
Glucocorticoid receptor binding	+	0.7971	79.71%
Aromatase binding	+	0.7057	70.57%
PPAR gamma	+	0.7168	71.68%
Honey bee toxicity	-	0.6411	64.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9894	98.94%

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	99.84%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.21%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.00%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.99%	96.38%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.90%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.87%	89.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.97%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.91%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.56%	93.56%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	87.51%	80.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.40%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.54%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.16%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.15%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.14%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	84.55%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.47%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.23%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.86%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.58%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.48%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.41%	91.24%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.30%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.10%	100.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.06%	85.31%

Plants that contains it

• Ligularia cymbulifera

Cross-Links

• PubChem: 162882751
• LOTUS: LTS0111221
• wikiData: Q105222968