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

Details

• Internal ID: 79c0fb20-d25d-4cf7-a0d5-e81d49560c20
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2S,3S,5R,6S)-6-acetyloxy-3-chloro-5-[(3R,5R)-3,6-dihydroxy-6-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-2-hydroxy-2-methylcyclohexyl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(CC(C1(C)O)Cl)C(=C)C(CC(C(C)(C)O)OC(=O)C(=CC)C)O)OC(=O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@H]([C@H](C[C@@H]([C@@]1(C)O)Cl)C(=C)[C@@H](C[C@H](C(C)(C)O)OC(=O)/C(=C\C)/C)O)OC(=O)C
• InChI: InChI=1S/C27H41ClO9/c1-10-14(3)24(31)36-21(26(7,8)33)13-19(30)16(5)18-12-20(28)27(9,34)23(22(18)35-17(6)29)37-25(32)15(4)11-2/h10-11,18-23,30,33-34H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t18-,19-,20+,21-,22+,23+,27-/m1/s1
• InChI Key: SIKUPEBRCUIQMC-IOZRVFGPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₁ClO₉
• Molecular Weight: 545.10 g/mol
• Exact Mass: 544.2439106 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9720	97.20%
Caco-2	-	0.7585	75.85%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8723	87.23%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8731	87.31%
OATP1B3 inhibitior	+	0.8886	88.86%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8841	88.41%
P-glycoprotein inhibitior	+	0.7022	70.22%
P-glycoprotein substrate	-	0.5241	52.41%
CYP3A4 substrate	+	0.6793	67.93%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.9019	90.19%
CYP3A4 inhibition	-	0.9185	91.85%
CYP2C9 inhibition	-	0.8330	83.30%
CYP2C19 inhibition	-	0.7232	72.32%
CYP2D6 inhibition	-	0.8983	89.83%
CYP1A2 inhibition	-	0.9277	92.77%
CYP2C8 inhibition	-	0.5995	59.95%
CYP inhibitory promiscuity	-	0.9277	92.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7907	79.07%
Carcinogenicity (trinary)	Non-required	0.6117	61.17%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9059	90.59%
Skin irritation	-	0.6174	61.74%
Skin corrosion	-	0.9200	92.00%
Ames mutagenesis	-	0.6078	60.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4825	48.25%
Micronuclear	-	0.6882	68.82%
Hepatotoxicity	+	0.7367	73.67%
skin sensitisation	-	0.5762	57.62%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7824	78.24%
Acute Oral Toxicity (c)	III	0.5906	59.06%
Estrogen receptor binding	+	0.7282	72.82%
Androgen receptor binding	+	0.5429	54.29%
Thyroid receptor binding	+	0.5586	55.86%
Glucocorticoid receptor binding	+	0.7288	72.88%
Aromatase binding	+	0.6255	62.55%
PPAR gamma	+	0.6176	61.76%
Honey bee toxicity	-	0.5117	51.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5148	51.48%
Fish aquatic toxicity	+	0.9961	99.61%

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	99.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.72%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	97.32%	89.34%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.29%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.84%	95.17%
CHEMBL284	P27487	Dipeptidyl peptidase IV	94.89%	95.69%
CHEMBL2581	P07339	Cathepsin D	93.84%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.09%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	91.01%	91.19%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.70%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.38%	89.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.89%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.37%	93.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.16%	96.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.33%	91.07%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.15%	92.29%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.82%	91.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.61%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.71%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.66%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.24%	95.50%

Plants that contains it

• Ligularia thyrsoidea

Cross-Links

• PubChem: 162861012
• LOTUS: LTS0227256
• wikiData: Q105253806