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

Details

• Internal ID: 11ab1d63-3256-42b6-9551-dab24600ca8c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aS,5R,6S,8aR,9aR)-6-hydroxy-3,4a,5-trimethyl-2-oxo-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(=O)OC2CC3C1(C(C(CC3)O)C)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C2=C(C(=O)O[C@@H]2C[C@@H]3[C@]1([C@H]([C@H](CC3)O)C)C)C
• InChI: InChI=1S/C20H28O5/c1-6-10(2)18(22)25-17-16-11(3)19(23)24-15(16)9-13-7-8-14(21)12(4)20(13,17)5/h6,12-15,17,21H,7-9H2,1-5H3/b10-6+/t12-,13+,14-,15+,17+,20+/m0/s1
• InChI Key: VHVVIDFLXPOQAK-LNHVGBMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 149475-46-7
• 2-Butenoic acid, 2-methyl-, 2,4,4a,5,6,7,8,8a,9,9a-decahydro-6-hydroxy-3,4a,5-trimethyl-2-oxonaphtho[2,3-b]furan-4-yl ester, [4S-[4alpha(E),4aalpha,5alpha,6alpha,8aalpha,9abeta]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.8100	81.00%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7984	79.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8658	86.58%
OATP1B3 inhibitior	+	0.9114	91.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.5904	59.04%
P-glycoprotein substrate	-	0.6094	60.94%
CYP3A4 substrate	+	0.6697	66.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8833	88.33%
CYP3A4 inhibition	-	0.6240	62.40%
CYP2C9 inhibition	-	0.8475	84.75%
CYP2C19 inhibition	-	0.9346	93.46%
CYP2D6 inhibition	-	0.9542	95.42%
CYP1A2 inhibition	-	0.6829	68.29%
CYP2C8 inhibition	-	0.7249	72.49%
CYP inhibitory promiscuity	-	0.9132	91.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4808	48.08%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9432	94.32%
Skin irritation	+	0.5630	56.30%
Skin corrosion	-	0.8604	86.04%
Ames mutagenesis	-	0.6364	63.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.8038	80.38%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6712	67.12%
skin sensitisation	-	0.7995	79.95%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5552	55.52%
Acute Oral Toxicity (c)	III	0.3975	39.75%
Estrogen receptor binding	+	0.7935	79.35%
Androgen receptor binding	+	0.6126	61.26%
Thyroid receptor binding	-	0.5255	52.55%
Glucocorticoid receptor binding	+	0.6762	67.62%
Aromatase binding	-	0.5436	54.36%
PPAR gamma	+	0.6747	67.47%
Honey bee toxicity	-	0.6978	69.78%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9761	97.61%

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	98.30%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.51%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.67%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.06%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.64%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.64%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.81%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.72%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.95%	91.07%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.21%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.86%	95.50%

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: 10043345
• NPASS: NPC283521
• LOTUS: LTS0026609
• wikiData: Q105286637