[(4S,4aS,5R,6S,8aR,9aS)-9a-methoxy-3,4a,5-trimethyl-6-[(Z)-3-methylsulfanylprop-2-enoyl]oxy-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 8617a87d-923f-4929-a251-b58393ff31c2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aS,5R,6S,8aR,9aS)-9a-methoxy-3,4a,5-trimethyl-6-[(Z)-3-methylsulfanylprop-2-enoyl]oxy-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(CC3C1(C(C(CC3)OC(=O)C=CSC)C)C)OC)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@H](CC3)OC(=O)/C=C\SC)C)C)OC)C
• InChI: InChI=1S/C25H34O7S/c1-8-14(2)22(27)31-21-20-15(3)23(28)32-25(20,29-6)13-17-9-10-18(16(4)24(17,21)5)30-19(26)11-12-33-7/h8,11-12,16-18,21H,9-10,13H2,1-7H3/b12-11-,14-8-/t16-,17+,18-,21+,24+,25-/m0/s1
• InChI Key: WAJCGTCCWFRXDF-WFXBQBEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₇S
• Molecular Weight: 478.60 g/mol
• Exact Mass: 478.20252459 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.33
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.5240	52.40%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7186	71.86%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8638	86.38%
OATP1B3 inhibitior	+	0.9669	96.69%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8510	85.10%
P-glycoprotein inhibitior	+	0.8825	88.25%
P-glycoprotein substrate	+	0.5363	53.63%
CYP3A4 substrate	+	0.7001	70.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8943	89.43%
CYP3A4 inhibition	-	0.6816	68.16%
CYP2C9 inhibition	-	0.8741	87.41%
CYP2C19 inhibition	-	0.8781	87.81%
CYP2D6 inhibition	-	0.9494	94.94%
CYP1A2 inhibition	-	0.5934	59.34%
CYP2C8 inhibition	+	0.6046	60.46%
CYP inhibitory promiscuity	-	0.7501	75.01%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5143	51.43%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.9348	93.48%
Skin irritation	-	0.5964	59.64%
Skin corrosion	-	0.8758	87.58%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.8511	85.11%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6669	66.69%
skin sensitisation	-	0.8009	80.09%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7403	74.03%
Acute Oral Toxicity (c)	III	0.5799	57.99%
Estrogen receptor binding	+	0.8671	86.71%
Androgen receptor binding	+	0.6373	63.73%
Thyroid receptor binding	+	0.7166	71.66%
Glucocorticoid receptor binding	+	0.8441	84.41%
Aromatase binding	+	0.7086	70.86%
PPAR gamma	+	0.8052	80.52%
Honey bee toxicity	-	0.6433	64.33%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9848	98.48%

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	97.92%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.25%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.71%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.10%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.70%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.86%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.52%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.60%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.24%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.79%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.31%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.08%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.48%	97.21%

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: 101942893
• NPASS: NPC267612
• LOTUS: LTS0217473
• wikiData: Q105300260