[(1S,2S,3S,5R,6S)-6-acetyloxy-3-chloro-5-[(3S)-4-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(Z)-2-methylbut-2-enoyl]oxybut-1-en-2-yl]-2-hydroxy-2-methylcyclohexyl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 985e2042-b868-4b63-ba47-96c46597f1bc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2S,3S,5R,6S)-6-acetyloxy-3-chloro-5-[(3S)-4-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(Z)-2-methylbut-2-enoyl]oxybut-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(CC2C(O2)(C)C)OC(=O)C(=CC)C)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]2C(O2)(C)C)OC(=O)/C(=C\C)/C)OC(=O)C
• InChI: InChI=1S/C27H39ClO8/c1-10-14(3)24(30)34-19(13-21-26(7,8)36-21)16(5)18-12-20(28)27(9,32)23(22(18)33-17(6)29)35-25(31)15(4)11-2/h10-11,18-23,32H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t18-,19+,20+,21+,22+,23+,27-/m1/s1
• InChI Key: XOBNWEYRIDTWMJ-DXIGDJAYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₉ClO₈
• Molecular Weight: 527.00 g/mol
• Exact Mass: 526.2333459 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.18
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.7208	72.08%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7960	79.60%
OATP2B1 inhibitior	-	0.7141	71.41%
OATP1B1 inhibitior	+	0.8609	86.09%
OATP1B3 inhibitior	+	0.8942	89.42%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9536	95.36%
P-glycoprotein inhibitior	+	0.7766	77.66%
P-glycoprotein substrate	-	0.5964	59.64%
CYP3A4 substrate	+	0.6697	66.97%
CYP2C9 substrate	-	0.8140	81.40%
CYP2D6 substrate	-	0.9019	90.19%
CYP3A4 inhibition	-	0.8340	83.40%
CYP2C9 inhibition	-	0.7978	79.78%
CYP2C19 inhibition	-	0.6292	62.92%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8368	83.68%
CYP2C8 inhibition	+	0.4543	45.43%
CYP inhibitory promiscuity	-	0.9163	91.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7307	73.07%
Carcinogenicity (trinary)	Non-required	0.5323	53.23%
Eye corrosion	-	0.9797	97.97%
Eye irritation	-	0.9094	90.94%
Skin irritation	-	0.6570	65.70%
Skin corrosion	-	0.9163	91.63%
Ames mutagenesis	-	0.5278	52.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4122	41.22%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	+	0.5442	54.42%
skin sensitisation	-	0.5844	58.44%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.7333	73.33%
Acute Oral Toxicity (c)	III	0.5700	57.00%
Estrogen receptor binding	+	0.7418	74.18%
Androgen receptor binding	+	0.5937	59.37%
Thyroid receptor binding	+	0.6431	64.31%
Glucocorticoid receptor binding	+	0.8155	81.55%
Aromatase binding	+	0.6660	66.60%
PPAR gamma	+	0.7292	72.92%
Honey bee toxicity	+	0.5441	54.41%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5393	53.93%
Fish aquatic toxicity	+	0.9937	99.37%

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	97.31%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.62%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.53%	97.25%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.16%	95.17%
CHEMBL340	P08684	Cytochrome P450 3A4	93.56%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.36%	96.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.28%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.47%	89.34%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.48%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.76%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.38%	91.24%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	84.29%	92.29%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.23%	98.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.92%	96.77%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.27%	93.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.11%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	82.84%	90.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.64%	82.50%
CHEMBL2581	P07339	Cathepsin D	82.47%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.74%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.03%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.03%	91.07%

Plants that contains it

• Ligularia thyrsoidea

Cross-Links

• PubChem: 163033908
• LOTUS: LTS0260830
• wikiData: Q105337671