[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-hydroxyprop-2-enoate

Details

• Internal ID: 2ddf91e5-5585-4c0a-9885-860c889b9aa2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-hydroxyprop-2-enoate
• InChI: InChI=1S/C18H20O6/c1-7-5-13(23-18(22)10(4)19)15-9(3)17(21)24-16(15)14-8(2)12(20)6-11(7)14/h11-16,19-20H,1-6H2/t11-,12-,13-,14-,15+,16+/m0/s1
• InChI Key: STQKFHDZSADKCG-OSLXHZNNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.30 g/mol
• Exact Mass: 332.12598835 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9707	97.07%
Caco-2	-	0.7234	72.34%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5762	57.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9384	93.84%
P-glycoprotein inhibitior	-	0.8683	86.83%
P-glycoprotein substrate	-	0.7895	78.95%
CYP3A4 substrate	+	0.6043	60.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8506	85.06%
CYP3A4 inhibition	-	0.8161	81.61%
CYP2C9 inhibition	-	0.8997	89.97%
CYP2C19 inhibition	-	0.8072	80.72%
CYP2D6 inhibition	-	0.9309	93.09%
CYP1A2 inhibition	-	0.8359	83.59%
CYP2C8 inhibition	-	0.7649	76.49%
CYP inhibitory promiscuity	-	0.9274	92.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5279	52.79%
Eye corrosion	-	0.9059	90.59%
Eye irritation	+	0.6290	62.90%
Skin irritation	-	0.6382	63.82%
Skin corrosion	-	0.8738	87.38%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7389	73.89%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.6782	67.82%
skin sensitisation	-	0.7715	77.15%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.8031	80.31%
Acute Oral Toxicity (c)	IV	0.4159	41.59%
Estrogen receptor binding	+	0.7196	71.96%
Androgen receptor binding	+	0.5796	57.96%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6283	62.83%
Aromatase binding	-	0.5211	52.11%
PPAR gamma	+	0.6221	62.21%
Honey bee toxicity	-	0.5476	54.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9204	92.04%

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	93.28%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	89.64%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.67%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.41%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.83%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.03%	91.19%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.41%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.05%	95.50%

Plants that contains it

• Cheirolophus teydis

Cross-Links

• PubChem: 163050638
• LOTUS: LTS0176345
• wikiData: Q105260515