[(1R,3R,4S,5S,6S)-3,5-dihydroxy-6-[(3S,5R)-5-hydroxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhepta-1,6-dien-2-yl]-3-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-2-oxocyclohexyl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: ff88beb0-1528-44ab-844e-f377f1900be3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3R,4S,5S,6S)-3,5-dihydroxy-6-[(3S,5R)-5-hydroxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhepta-1,6-dien-2-yl]-3-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-2-oxocyclohexyl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C(C(C1=O)(C)O)OC(=O)C(=CC)C)O)C(=C)C(CC(C(=C)C)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@@](C1=O)(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
• InChI: InChI=1S/C30H42O10/c1-11-16(6)27(34)38-21(14-20(31)15(4)5)19(9)22-23(32)26(40-29(36)18(8)13-3)30(10,37)25(33)24(22)39-28(35)17(7)12-2/h11-13,20-24,26,31-32,37H,4,9,14H2,1-3,5-8,10H3/b16-11-,17-12-,18-13-/t20-,21+,22+,23+,24-,26+,30+/m1/s1
• InChI Key: FYZXLNYZJHWILH-PERZTNANSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₁₀
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.27779753 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9315	93.15%
Caco-2	-	0.8243	82.43%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7427	74.27%
OATP2B1 inhibitior	-	0.5730	57.30%
OATP1B1 inhibitior	+	0.8642	86.42%
OATP1B3 inhibitior	+	0.9327	93.27%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8375	83.75%
P-glycoprotein inhibitior	+	0.7369	73.69%
P-glycoprotein substrate	-	0.5401	54.01%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.9060	90.60%
CYP3A4 inhibition	-	0.8235	82.35%
CYP2C9 inhibition	-	0.9080	90.80%
CYP2C19 inhibition	-	0.8410	84.10%
CYP2D6 inhibition	-	0.9038	90.38%
CYP1A2 inhibition	-	0.9486	94.86%
CYP2C8 inhibition	-	0.7184	71.84%
CYP inhibitory promiscuity	-	0.9499	94.99%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7682	76.82%
Carcinogenicity (trinary)	Non-required	0.7054	70.54%
Eye corrosion	-	0.9726	97.26%
Eye irritation	-	0.8922	89.22%
Skin irritation	-	0.5665	56.65%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5979	59.79%
Micronuclear	-	0.5582	55.82%
Hepatotoxicity	+	0.7051	70.51%
skin sensitisation	+	0.5857	58.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.6380	63.80%
Acute Oral Toxicity (c)	III	0.4901	49.01%
Estrogen receptor binding	+	0.7131	71.31%
Androgen receptor binding	-	0.5548	55.48%
Thyroid receptor binding	+	0.6448	64.48%
Glucocorticoid receptor binding	+	0.7547	75.47%
Aromatase binding	+	0.6315	63.15%
PPAR gamma	+	0.6598	65.98%
Honey bee toxicity	-	0.6305	63.05%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9504	95.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.95%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.78%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.19%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.96%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.07%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.59%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	87.66%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.35%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.33%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.07%	91.24%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	84.46%	80.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.89%	90.08%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.19%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.55%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.35%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.22%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.68%	99.17%

Plants that contains it

• Ligularia dentata

Cross-Links

• PubChem: 163000037
• LOTUS: LTS0045284
• wikiData: Q105004821