(Z)-2-Methyl-2-butenoic acid (S)-(3beta-hydroxy-1beta,2beta-dimethyl-6-oxocyclohexyl)[[(R)-2,5-dihydro-5-hydroxy-4-methyl-2-oxofuran]-3-yl]methyl ester

Details

• Internal ID: 6c74f48f-1461-4efa-9a2d-59238dc26a19
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(S)-[(1S,2R,3S)-3-hydroxy-1,2-dimethyl-6-oxocyclohexyl]-[(2R)-2-hydroxy-3-methyl-5-oxo-2H-furan-4-yl]methyl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC(C1=C(C(OC1=O)O)C)C2(C(C(CCC2=O)O)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H](C1=C([C@@H](OC1=O)O)C)[C@@]2([C@H]([C@H](CCC2=O)O)C)C
• InChI: InChI=1S/C19H26O7/c1-6-9(2)16(22)25-15(14-10(3)17(23)26-18(14)24)19(5)11(4)12(20)7-8-13(19)21/h6,11-12,15,17,20,23H,7-8H2,1-5H3/b9-6-/t11-,12-,15+,17+,19+/m0/s1
• InChI Key: JNKNAUQBPPWDQQ-HBAXVLCVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.16785316 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (Z)-2-Methyl-2-butenoic acid (S)-(3beta-hydroxy-1beta,2beta-dimethyl-6-oxocyclohexyl)[[(R)-2,5-dihydro-5-hydroxy-4-methyl-2-oxofuran]-3-yl]methyl ester
• 178402-70-5
• 2-Butenoic acid, 2-methyl-, (2,5-dihydro-5-hydroxy-4-methyl-2-oxo-3-furanyl)(3-hydroxy-1,2-dimethyl-6-oxocyclohexyl)methyl ester, [1S-[1alpha[1R*(Z),1(S*)],2beta,3beta]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9748	97.48%
Caco-2	+	0.6229	62.29%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7780	77.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8838	88.38%
OATP1B3 inhibitior	+	0.9223	92.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7771	77.71%
BSEP inhibitior	-	0.5786	57.86%
P-glycoprotein inhibitior	-	0.5969	59.69%
P-glycoprotein substrate	-	0.6917	69.17%
CYP3A4 substrate	+	0.6337	63.37%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8928	89.28%
CYP3A4 inhibition	-	0.8475	84.75%
CYP2C9 inhibition	-	0.8766	87.66%
CYP2C19 inhibition	-	0.9078	90.78%
CYP2D6 inhibition	-	0.9526	95.26%
CYP1A2 inhibition	-	0.8252	82.52%
CYP2C8 inhibition	-	0.8046	80.46%
CYP inhibitory promiscuity	-	0.9153	91.53%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9253	92.53%
Carcinogenicity (trinary)	Non-required	0.5506	55.06%
Eye corrosion	-	0.9797	97.97%
Eye irritation	-	0.9459	94.59%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8393	83.93%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6706	67.06%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6190	61.90%
skin sensitisation	-	0.7461	74.61%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5634	56.34%
Acute Oral Toxicity (c)	III	0.4423	44.23%
Estrogen receptor binding	+	0.6209	62.09%
Androgen receptor binding	+	0.5641	56.41%
Thyroid receptor binding	-	0.5355	53.55%
Glucocorticoid receptor binding	+	0.6215	62.15%
Aromatase binding	-	0.4891	48.91%
PPAR gamma	+	0.6702	67.02%
Honey bee toxicity	-	0.7592	75.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8695	86.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.41%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.00%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.07%	98.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.64%	98.75%
CHEMBL1937	Q92769	Histone deacetylase 2	87.43%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.28%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.94%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.96%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.41%	89.00%
CHEMBL325	Q13547	Histone deacetylase 1	83.39%	95.92%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.11%	96.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.52%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.27%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.03%	93.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.47%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.06%	99.17%

Plants that contains it

• Acacia paradoxa
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Isophysis tasmanica
• Matricaria discoidea
• Metasequoia glyptostroboides
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 101993910
• NPASS: NPC247359
• LOTUS: LTS0142933
• wikiData: Q105131970