methyl (3aS,4S,5S,6E,11S,11aS)-11-hydroxy-5-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-4-(2-methylbutanoyloxy)-3,10-dimethylidene-2-oxo-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-6-carboxylate

Details

• Internal ID: d461a934-4063-4f40-9b1f-611d91de5cbe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: methyl (3aS,4S,5S,6E,11S,11aS)-11-hydroxy-5-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-4-(2-methylbutanoyloxy)-3,10-dimethylidene-2-oxo-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(C(C(=C)CCC=C(C1OC(=O)C(=CC)CO)C(=O)OC)O)OC(=O)C2=C
• SMILES (Isomeric): CCC(C)C(=O)O[C@H]1[C@@H]2[C@@H]([C@H](C(=C)CC/C=C(\[C@@H]1OC(=O)/C(=C\C)/CO)/C(=O)OC)O)OC(=O)C2=C
• InChI: InChI=1S/C26H34O10/c1-7-13(3)23(29)36-22-18-15(5)24(30)35-21(18)19(28)14(4)10-9-11-17(26(32)33-6)20(22)34-25(31)16(8-2)12-27/h8,11,13,18-22,27-28H,4-5,7,9-10,12H2,1-3,6H3/b16-8-,17-11+/t13?,18-,19-,20-,21-,22-/m0/s1
• InChI Key: IVQFRPZHDFKKNP-XTCMNXESSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₀
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.21519728 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9678	96.78%
Caco-2	-	0.7300	73.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6278	62.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8250	82.50%
OATP1B3 inhibitior	+	0.9124	91.24%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7034	70.34%
P-glycoprotein inhibitior	+	0.6722	67.22%
P-glycoprotein substrate	+	0.5429	54.29%
CYP3A4 substrate	+	0.6448	64.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9015	90.15%
CYP3A4 inhibition	+	0.5458	54.58%
CYP2C9 inhibition	-	0.6789	67.89%
CYP2C19 inhibition	-	0.7421	74.21%
CYP2D6 inhibition	-	0.8882	88.82%
CYP1A2 inhibition	-	0.5178	51.78%
CYP2C8 inhibition	+	0.5061	50.61%
CYP inhibitory promiscuity	-	0.7622	76.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6417	64.17%
Eye corrosion	-	0.9772	97.72%
Eye irritation	-	0.8806	88.06%
Skin irritation	-	0.6646	66.46%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6127	61.27%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8576	85.76%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6551	65.51%
Acute Oral Toxicity (c)	III	0.4546	45.46%
Estrogen receptor binding	+	0.6336	63.36%
Androgen receptor binding	+	0.5516	55.16%
Thyroid receptor binding	-	0.5140	51.40%
Glucocorticoid receptor binding	+	0.7116	71.16%
Aromatase binding	-	0.5629	56.29%
PPAR gamma	+	0.5727	57.27%
Honey bee toxicity	-	0.7194	71.94%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9468	94.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.77%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.38%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.18%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.51%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.05%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	88.72%	94.73%
CHEMBL299	P17252	Protein kinase C alpha	88.06%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.01%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	85.80%	97.79%
CHEMBL226	P30542	Adenosine A1 receptor	85.28%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.93%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.92%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.46%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.36%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.72%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.37%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	82.26%	92.50%
CHEMBL5028	O14672	ADAM10	81.38%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.15%	99.17%

Plants that contains it

• Tetragonotheca repanda

Cross-Links

• PubChem: 101532555
• LOTUS: LTS0145899
• wikiData: Q105121226