(4S,4aS,5R,6S,8aR,9aR)-2,4,4a,5,6,7,8,8a,9,9a-Decahydro-3,4a,5-trimethyl-6-[[(2E)-3-[(R)-methylsulfinyl]-1-oxo-2-propen-1-yl]oxy]-2-oxonaphtho[2,3-b]furan-4-yl (2Z)-2-methyl-2-butenoate

Details

• Internal ID: 0adc5ecb-6801-4ed1-91a6-1ace441be017
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aS,5R,6S,8aR,9aR)-3,4a,5-trimethyl-6-[(E)-3-[(R)-methylsulfinyl]prop-2-enoyl]oxy-2-oxo-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(=O)OC2CC3C1(C(C(CC3)OC(=O)C=CS(=O)C)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)OC(=O)/C=C/[S@](=O)C)C)C)C
• InChI: InChI=1S/C24H32O7S/c1-7-13(2)22(26)31-21-20-14(3)23(27)30-18(20)12-16-8-9-17(15(4)24(16,21)5)29-19(25)10-11-32(6)28/h7,10-11,15-18,21H,8-9,12H2,1-6H3/b11-10+,13-7-/t15-,16+,17-,18+,21+,24+,32+/m0/s1
• InChI Key: VIUDBOBKMBZVGZ-IVBSSVFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₇S
• Molecular Weight: 464.60 g/mol
• Exact Mass: 464.18687453 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.37
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• (4S,4aS,5R,6S,8aR,9aR)-2,4,4a,5,6,7,8,8a,9,9a-Decahydro-3,4a,5-trimethyl-6-[[(2E)-3-[(R)-methylsulfinyl]-1-oxo-2-propen-1-yl]oxy]-2-oxonaphtho[2,3-b]furan-4-yl (2Z)-2-methyl-2-butenoate
• 182127-79-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	-	0.5374	53.74%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4589	45.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8631	86.31%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8411	84.11%
P-glycoprotein inhibitior	+	0.8782	87.82%
P-glycoprotein substrate	+	0.5420	54.20%
CYP3A4 substrate	+	0.6971	69.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9063	90.63%
CYP3A4 inhibition	+	0.5191	51.91%
CYP2C9 inhibition	-	0.7715	77.15%
CYP2C19 inhibition	-	0.7357	73.57%
CYP2D6 inhibition	-	0.8999	89.99%
CYP1A2 inhibition	-	0.6005	60.05%
CYP2C8 inhibition	+	0.5391	53.91%
CYP inhibitory promiscuity	-	0.7179	71.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7300	73.00%
Carcinogenicity (trinary)	Non-required	0.5737	57.37%
Eye corrosion	-	0.9743	97.43%
Eye irritation	-	0.9556	95.56%
Skin irritation	-	0.7142	71.42%
Skin corrosion	-	0.8937	89.37%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8272	82.72%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5982	59.82%
skin sensitisation	-	0.8203	82.03%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6015	60.15%
Acute Oral Toxicity (c)	III	0.5471	54.71%
Estrogen receptor binding	+	0.8065	80.65%
Androgen receptor binding	+	0.6139	61.39%
Thyroid receptor binding	+	0.6075	60.75%
Glucocorticoid receptor binding	+	0.8080	80.80%
Aromatase binding	+	0.5384	53.84%
PPAR gamma	+	0.6845	68.45%
Honey bee toxicity	-	0.6643	66.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9880	98.80%

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	98.28%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	93.47%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.64%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.30%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.09%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.57%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.00%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.72%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.53%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.02%	95.50%
CHEMBL4302	P08183	P-glycoprotein 1	83.03%	92.98%
CHEMBL2581	P07339	Cathepsin D	82.34%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.23%	92.94%

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: 10837859
• NPASS: NPC251418
• LOTUS: LTS0187436
• wikiData: Q105287018