[(3S,3aR,4S,5aR,9bS)-3,5a,9-trimethyl-2,6-dioxo-3a,4,5,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-4-yl] acetate

Details

• Internal ID: 684d6a69-a0e8-4e3f-a280-b39082ca8fe0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aR,4S,5aR,9bS)-3,5a,9-trimethyl-2,6-dioxo-3a,4,5,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-4-yl] acetate
• InChI: InChI=1S/C17H22O5/c1-8-5-6-12(19)17(4)7-11(21-10(3)18)13-9(2)16(20)22-15(13)14(8)17/h9,11,13,15H,5-7H2,1-4H3/t9-,11-,13+,15-,17-/m0/s1
• InChI Key: ATWFGCRPHGGEQP-BZDSGMRHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.6938	69.38%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7155	71.55%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9009	90.09%
OATP1B3 inhibitior	+	0.8892	88.92%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8056	80.56%
P-glycoprotein inhibitior	-	0.6177	61.77%
P-glycoprotein substrate	-	0.8559	85.59%
CYP3A4 substrate	+	0.6313	63.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.6761	67.61%
CYP2C9 inhibition	-	0.8430	84.30%
CYP2C19 inhibition	-	0.8784	87.84%
CYP2D6 inhibition	-	0.9632	96.32%
CYP1A2 inhibition	+	0.5076	50.76%
CYP2C8 inhibition	-	0.8392	83.92%
CYP inhibitory promiscuity	-	0.8477	84.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5416	54.16%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.6685	66.85%
Skin irritation	+	0.5787	57.87%
Skin corrosion	-	0.8883	88.83%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6522	65.22%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.8119	81.19%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6785	67.85%
Acute Oral Toxicity (c)	III	0.6074	60.74%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5281	52.81%
Thyroid receptor binding	+	0.5431	54.31%
Glucocorticoid receptor binding	-	0.5395	53.95%
Aromatase binding	-	0.7515	75.15%
PPAR gamma	-	0.5221	52.21%
Honey bee toxicity	-	0.7060	70.60%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.10%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.53%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.40%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.26%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.18%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	86.72%	89.63%
CHEMBL2581	P07339	Cathepsin D	85.91%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.59%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.21%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	84.05%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.45%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.02%	91.19%

Plants that contains it

• Artemisia herba-alba

Cross-Links

• PubChem: 101248755
• LOTUS: LTS0242109
• wikiData: Q104918723