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

Details

• Internal ID: c90f4890-999b-4e4d-b76e-21d533f8c5c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aS,5R,6S,8aR,9aR)-3,4a,5-trimethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2CC3C(=C(C(=O)O3)C)C(C2(C1C)C)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@@H]2C[C@@H]3C(=C(C(=O)O3)C)[C@H]([C@@]2([C@H]1C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C25H34O6/c1-8-13(3)22(26)29-18-11-10-17-12-19-20(15(5)24(28)30-19)21(25(17,7)16(18)6)31-23(27)14(4)9-2/h8-9,16-19,21H,10-12H2,1-7H3/b13-8-,14-9-/t16-,17+,18-,19+,21+,25+/m0/s1
• InChI Key: GNUFDZISEWLEOG-WNLUJWOHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₆
• Molecular Weight: 430.50 g/mol
• Exact Mass: 430.23553880 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.44
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 149475-47-8
• 2-Butenoic acid, 2-methyl-, 2,4,4a,5,6,7,8,8a,9,9a-decahydro-3,4a,5-trimethyl-2-oxonaphtho[2,3-b]furan-4,6-diyl ester, [4S-[4alpha(Z),4aalpha,5alpha,6alpha(Z),8aalpha,9abeta]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.5885	58.85%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7454	74.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8757	87.57%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8741	87.41%
P-glycoprotein inhibitior	+	0.8408	84.08%
P-glycoprotein substrate	-	0.6353	63.53%
CYP3A4 substrate	+	0.6627	66.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8923	89.23%
CYP3A4 inhibition	-	0.6011	60.11%
CYP2C9 inhibition	-	0.8591	85.91%
CYP2C19 inhibition	-	0.8989	89.89%
CYP2D6 inhibition	-	0.9539	95.39%
CYP1A2 inhibition	+	0.5273	52.73%
CYP2C8 inhibition	-	0.7160	71.60%
CYP inhibitory promiscuity	-	0.7493	74.93%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4872	48.72%
Eye corrosion	-	0.9780	97.80%
Eye irritation	-	0.8982	89.82%
Skin irritation	+	0.5210	52.10%
Skin corrosion	-	0.8249	82.49%
Ames mutagenesis	-	0.5764	57.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.8732	87.32%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.7033	70.33%
skin sensitisation	-	0.7660	76.60%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7049	70.49%
Acute Oral Toxicity (c)	III	0.6708	67.08%
Estrogen receptor binding	+	0.8788	87.88%
Androgen receptor binding	+	0.5810	58.10%
Thyroid receptor binding	+	0.5655	56.55%
Glucocorticoid receptor binding	+	0.8255	82.55%
Aromatase binding	+	0.5907	59.07%
PPAR gamma	+	0.7425	74.25%
Honey bee toxicity	-	0.6788	67.88%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9881	98.81%

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	97.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.70%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	91.44%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.44%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.43%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.46%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.24%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.40%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.02%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.94%	91.07%
CHEMBL221	P23219	Cyclooxygenase-1	81.75%	90.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.04%	94.00%

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
• Triadica sebifera

Cross-Links

• PubChem: 10455374
• NPASS: NPC225773
• LOTUS: LTS0207975
• wikiData: Q105013341