[(3aR,4R,6aR,7R,9aR,9bR)-7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-(acetyloxymethyl)-4-hydroxybut-2-enoate

Details

• Internal ID: 3775d1e5-6567-4f13-b090-d2580226302f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,7R,9aR,9bR)-7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-(acetyloxymethyl)-4-hydroxybut-2-enoate
• InChI: InChI=1S/C22H26O8/c1-10-7-15(25)17-11(2)8-16(19-12(3)21(26)30-20(19)18(10)17)29-22(27)14(5-6-23)9-28-13(4)24/h5,7,15-20,23,25H,2-3,6,8-9H2,1,4H3/b14-5+/t15-,16-,17-,18+,19-,20-/m1/s1
• InChI Key: AYKIKNPTNIJPRW-UDTPUXAFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₈
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.16276778 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.99
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9382	93.82%
Caco-2	-	0.8141	81.41%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6722	67.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8687	86.87%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6957	69.57%
P-glycoprotein inhibitior	-	0.5659	56.59%
P-glycoprotein substrate	-	0.6315	63.15%
CYP3A4 substrate	+	0.6421	64.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9015	90.15%
CYP3A4 inhibition	-	0.8016	80.16%
CYP2C9 inhibition	-	0.8486	84.86%
CYP2C19 inhibition	-	0.7741	77.41%
CYP2D6 inhibition	-	0.9170	91.70%
CYP1A2 inhibition	-	0.7300	73.00%
CYP2C8 inhibition	-	0.6211	62.11%
CYP inhibitory promiscuity	-	0.7885	78.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6663	66.63%
Eye corrosion	-	0.9676	96.76%
Eye irritation	-	0.8757	87.57%
Skin irritation	-	0.6878	68.78%
Skin corrosion	-	0.9107	91.07%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5604	56.04%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7980	79.80%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7170	71.70%
Acute Oral Toxicity (c)	III	0.4008	40.08%
Estrogen receptor binding	+	0.7802	78.02%
Androgen receptor binding	+	0.5979	59.79%
Thyroid receptor binding	-	0.5374	53.74%
Glucocorticoid receptor binding	+	0.7893	78.93%
Aromatase binding	+	0.5562	55.62%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7103	71.03%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9600	96.00%

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	96.15%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.17%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.51%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.17%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.64%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.57%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.07%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	82.63%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.18%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.01%	89.00%

Plants that contains it

• Chaenactis douglasii
• Helogyne apaloidea

Cross-Links

• PubChem: 13994666
• LOTUS: LTS0148920
• wikiData: Q104921167