[(1R,2R,3R,4R,5R,6R)-6-[(3S,5S)-5,6-dihydroxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-2,3,5-trihydroxy-3-methyl-4-[(Z)-2-methylbut-2-enoyl]oxycyclohexyl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 1fea0aaf-aca8-4ec0-8f38-3b7943c3b104
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2R,3R,4R,5R,6R)-6-[(3S,5S)-5,6-dihydroxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-2,3,5-trihydroxy-3-methyl-4-[(Z)-2-methylbut-2-enoyl]oxycyclohexyl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C(C(C1O)(C)O)OC(=O)C(=CC)C)O)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@H]([C@H]([C@]([C@@H]1O)(C)O)OC(=O)/C(=C\C)/C)O)C(=C)[C@H](C[C@@H](C(C)(C)O)O)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C30H46O11/c1-11-15(4)26(34)39-19(14-20(31)29(8,9)37)18(7)21-22(32)25(41-28(36)17(6)13-3)30(10,38)24(33)23(21)40-27(35)16(5)12-2/h11-13,19-25,31-33,37-38H,7,14H2,1-6,8-10H3/b15-11-,16-12-,17-13-/t19-,20-,21+,22+,23+,24+,25+,30+/m0/s1
• InChI Key: QKHLXIGZDTZQSV-QJJNOYIXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₁₁
• Molecular Weight: 582.70 g/mol
• Exact Mass: 582.30401228 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9246	92.46%
Caco-2	-	0.8075	80.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8030	80.30%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8784	87.84%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8298	82.98%
P-glycoprotein inhibitior	+	0.7131	71.31%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6481	64.81%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.8617	86.17%
CYP2C9 inhibition	-	0.8400	84.00%
CYP2C19 inhibition	-	0.8348	83.48%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.9369	93.69%
CYP2C8 inhibition	-	0.7244	72.44%
CYP inhibitory promiscuity	-	0.9641	96.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8654	86.54%
Carcinogenicity (trinary)	Non-required	0.6981	69.81%
Eye corrosion	-	0.9801	98.01%
Eye irritation	-	0.8958	89.58%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.5078	50.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.3972	39.72%
Micronuclear	-	0.5882	58.82%
Hepatotoxicity	+	0.6249	62.49%
skin sensitisation	+	0.5636	56.36%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5332	53.32%
Acute Oral Toxicity (c)	III	0.4909	49.09%
Estrogen receptor binding	+	0.7233	72.33%
Androgen receptor binding	-	0.5149	51.49%
Thyroid receptor binding	+	0.6494	64.94%
Glucocorticoid receptor binding	+	0.7282	72.82%
Aromatase binding	+	0.6552	65.52%
PPAR gamma	+	0.6938	69.38%
Honey bee toxicity	-	0.6216	62.16%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9740	97.40%

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	97.62%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.38%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.03%	91.07%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.74%	89.34%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.25%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.14%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.04%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.53%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.14%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	82.94%	90.17%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.89%	94.97%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.78%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.49%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.39%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.91%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.47%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.43%	95.89%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.32%	80.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.18%	89.50%

Plants that contains it

• Ligularia lankongensis

Cross-Links

• PubChem: 162979033
• LOTUS: LTS0201930
• wikiData: Q105223119