(Z)-2-Methyl-2-butenoic acid [(4S)-2-oxo-3,4abeta,5beta-trimethyl-6beta,9beta,9abeta-trihydroxy-2,4,4a,5,6,7,8,8abeta,9,9a-decahydronaphtho[2,3-b]furan]-4beta-yl ester

Details

• Internal ID: e9e1775a-5ea6-489f-9feb-106467437191
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aR,5R,6S,8aS,9R,9aR)-6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(=O)OC2(C(C3C1(C(C(CC3)O)C)C)O)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C(C(=O)O[C@]2([C@@H]([C@@H]3[C@]1([C@H]([C@H](CC3)O)C)C)O)O)C
• InChI: InChI=1S/C20H28O7/c1-6-9(2)17(23)26-16-14-10(3)18(24)27-20(14,25)15(22)12-7-8-13(21)11(4)19(12,16)5/h6,11-13,15-16,21-22,25H,7-8H2,1-5H3/b9-6-/t11-,12+,13-,15+,16+,19+,20+/m0/s1
• InChI Key: MSDFIROCDXOIAM-XPPKGDLMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• (Z)-2-Methyl-2-butenoic acid [(4S)-2-oxo-3,4abeta,5beta-trimethyl-6beta,9beta,9abeta-trihydroxy-2,4,4a,5,6,7,8,8abeta,9,9a-decahydronaphtho[2,3-b]furan]-4beta-yl ester
• 171422-89-2
• 2-Butenoic acid, 2-methyl-, 2,4,4a,5,6,7,8,8a,9,9a-decahydro-6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxonaphtho[2,3-b]furan-4-yl ester, [4S-[4alpha(Z),4aalpha,5alpha,6alpha,8aalpha,9alpha,9aalpha]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9708	97.08%
Caco-2	+	0.5128	51.28%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8636	86.36%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6842	68.42%
BSEP inhibitior	-	0.5178	51.78%
P-glycoprotein inhibitior	-	0.7075	70.75%
P-glycoprotein substrate	-	0.6926	69.26%
CYP3A4 substrate	+	0.6848	68.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8763	87.63%
CYP3A4 inhibition	-	0.7069	70.69%
CYP2C9 inhibition	-	0.7993	79.93%
CYP2C19 inhibition	-	0.8412	84.12%
CYP2D6 inhibition	-	0.9216	92.16%
CYP1A2 inhibition	-	0.6309	63.09%
CYP2C8 inhibition	-	0.7148	71.48%
CYP inhibitory promiscuity	-	0.9078	90.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4109	41.09%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9412	94.12%
Skin irritation	+	0.5532	55.32%
Skin corrosion	-	0.8528	85.28%
Ames mutagenesis	-	0.6064	60.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.6936	69.36%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8273	82.73%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6950	69.50%
Acute Oral Toxicity (c)	III	0.3391	33.91%
Estrogen receptor binding	+	0.6627	66.27%
Androgen receptor binding	+	0.6664	66.64%
Thyroid receptor binding	-	0.5146	51.46%
Glucocorticoid receptor binding	+	0.7025	70.25%
Aromatase binding	+	0.5876	58.76%
PPAR gamma	+	0.5289	52.89%
Honey bee toxicity	-	0.6589	65.89%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9441	94.41%

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	96.94%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.83%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.08%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.58%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.75%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.53%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	86.43%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.12%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.50%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.64%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.14%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.01%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.84%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.29%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.73%	94.45%

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: 10523815
• NPASS: NPC274739
• LOTUS: LTS0099642
• wikiData: Q105171106