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

Details

• Internal ID: cd970076-729b-48d8-936e-9cc6dbc50395
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2R,3S,5R,6S)-5-[(3R,5R)-3,6-dihydroxy-6-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-2,3,6-trihydroxy-2-methylcyclohexyl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(CC(C1(C)O)O)C(=C)C(CC(C(C)(C)O)OC(=O)C(=CC)C)O)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@H]([C@H](C[C@@H]([C@@]1(C)O)O)C(=C)[C@@H](C[C@H](C(C)(C)O)OC(=O)/C(=C\C)/C)O)O
• InChI: InChI=1S/C25H40O9/c1-9-13(3)22(29)33-19(24(6,7)31)12-17(26)15(5)16-11-18(27)25(8,32)21(20(16)28)34-23(30)14(4)10-2/h9-10,16-21,26-28,31-32H,5,11-12H2,1-4,6-8H3/b13-9-,14-10-/t16-,17-,18+,19-,20+,21+,25-/m1/s1
• InChI Key: LGRBNEWZMTYTSW-FLEZKLDCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₀O₉
• Molecular Weight: 484.60 g/mol
• Exact Mass: 484.26723285 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8825	88.25%
Caco-2	-	0.7683	76.83%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8252	82.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9114	91.14%
OATP1B3 inhibitior	+	0.9042	90.42%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4504	45.04%
P-glycoprotein inhibitior	-	0.4726	47.26%
P-glycoprotein substrate	+	0.5209	52.09%
CYP3A4 substrate	+	0.6514	65.14%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.8986	89.86%
CYP2C9 inhibition	-	0.8254	82.54%
CYP2C19 inhibition	-	0.7574	75.74%
CYP2D6 inhibition	-	0.9041	90.41%
CYP1A2 inhibition	-	0.9259	92.59%
CYP2C8 inhibition	-	0.6890	68.90%
CYP inhibitory promiscuity	-	0.9596	95.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.7250	72.50%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.8964	89.64%
Skin irritation	-	0.6432	64.32%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	-	0.6078	60.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4335	43.35%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	+	0.6570	65.70%
skin sensitisation	-	0.5630	56.30%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5561	55.61%
Acute Oral Toxicity (c)	III	0.4510	45.10%
Estrogen receptor binding	+	0.6654	66.54%
Androgen receptor binding	-	0.5187	51.87%
Thyroid receptor binding	+	0.5191	51.91%
Glucocorticoid receptor binding	+	0.6719	67.19%
Aromatase binding	+	0.5852	58.52%
PPAR gamma	+	0.5851	58.51%
Honey bee toxicity	-	0.5701	57.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9864	98.64%

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	99.32%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.99%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.09%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.01%	89.34%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	91.31%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.88%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.78%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.53%	91.07%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.43%	96.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.32%	94.45%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.23%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	86.08%	91.19%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.85%	90.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.71%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.93%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.47%	95.17%
CHEMBL221	P23219	Cyclooxygenase-1	84.04%	90.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.94%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.51%	94.33%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.86%	95.69%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.47%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.09%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.18%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.80%	97.21%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.55%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.48%	93.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.33%	91.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.03%	100.00%

Plants that contains it

• Ligularia cymbulifera

Cross-Links

• PubChem: 162847118
• LOTUS: LTS0205935
• wikiData: Q105151540