2-Butenoic acid, 2-methyl-, 2,4,4a,5,6,7,8,8a,9,9a-decahydro-9a-hydroxy-3,4a,5-trimethyl-2,6-dioxonaphtho[2,3-b]furan-4-yl ester, [4S-[4alpha(Z),4aalpha,5alpha,8aalpha,9aalpha]]-

Details

• Internal ID: e12dd1e9-e13b-4a8c-b968-49dc4d6d09b1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-2,6-dioxo-4,5,7,8,8a,9-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(=O)OC2(CC3C1(C(C(=O)CC3)C)C)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C(C(=O)O[C@]2(C[C@@H]3[C@]1([C@H](C(=O)CC3)C)C)O)C
• InChI: InChI=1S/C20H26O6/c1-6-10(2)17(22)25-16-15-11(3)18(23)26-20(15,24)9-13-7-8-14(21)12(4)19(13,16)5/h6,12-13,16,24H,7-9H2,1-5H3/b10-6-/t12-,13+,16+,19+,20-/m0/s1
• InChI Key: WKMBTXJFBQEZHO-PTCPTGMSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 162613-68-5
• 2-Butenoic acid, 2-methyl-, 2,4,4a,5,6,7,8,8a,9,9a-decahydro-9a-hydroxy-3,4a,5-trimethyl-2,6-dioxonaphtho[2,3-b]furan-4-yl ester, [4S-[4alpha(Z),4aalpha,5alpha,8aalpha,9aalpha]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.7085	70.85%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7689	76.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8867	88.67%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.7496	74.96%
P-glycoprotein inhibitior	-	0.6206	62.06%
P-glycoprotein substrate	-	0.7050	70.50%
CYP3A4 substrate	+	0.6593	65.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8946	89.46%
CYP3A4 inhibition	-	0.5785	57.85%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.9208	92.08%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	+	0.5225	52.25%
CYP2C8 inhibition	-	0.6776	67.76%
CYP inhibitory promiscuity	-	0.8620	86.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4294	42.94%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8949	89.49%
Skin irritation	+	0.6376	63.76%
Skin corrosion	-	0.8543	85.43%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8121	81.21%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6418	64.18%
skin sensitisation	-	0.8170	81.70%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.7290	72.90%
Acute Oral Toxicity (c)	III	0.5065	50.65%
Estrogen receptor binding	+	0.7102	71.02%
Androgen receptor binding	+	0.6032	60.32%
Thyroid receptor binding	+	0.5737	57.37%
Glucocorticoid receptor binding	+	0.6679	66.79%
Aromatase binding	+	0.5309	53.09%
PPAR gamma	+	0.5909	59.09%
Honey bee toxicity	-	0.7504	75.04%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9751	97.51%

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	97.74%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.96%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.70%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.68%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.32%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.04%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.83%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.57%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.64%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.19%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.98%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.23%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.49%	100.00%

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
• Strychnos chrysophylla
• Strychnos longicaudata
• Strychnos matopensis
• Strychnos mimfiensis
• Strychnos nux-vomica
• Strychnos trinervis
• Triadica sebifera

Cross-Links

• PubChem: 10428722
• NPASS: NPC231336
• LOTUS: LTS0140443
• wikiData: Q105214865