(3,6,9-Trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl) 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 8aa2e565-58e4-47dd-bd89-d3e123042d22
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl) 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): C=C1CCC2C1C3C(C(CC2=C)OC(=O)C(=C)CO)C(=C)C(=O)O3
• SMILES (Isomeric): C=C1CCC2C1C3C(C(CC2=C)OC(=O)C(=C)CO)C(=C)C(=O)O3
• InChI: InChI=1S/C19H22O5/c1-9-5-6-13-10(2)7-14(23-18(21)11(3)8-20)16-12(4)19(22)24-17(16)15(9)13/h13-17,20H,1-8H2
• InChI Key: PHJYCLCTXRJHJZ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.6089	60.89%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7169	71.69%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9097	90.97%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9025	90.25%
P-glycoprotein inhibitior	-	0.7387	73.87%
P-glycoprotein substrate	-	0.7317	73.17%
CYP3A4 substrate	+	0.6117	61.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	-	0.8115	81.15%
CYP2C9 inhibition	-	0.8555	85.55%
CYP2C19 inhibition	-	0.8219	82.19%
CYP2D6 inhibition	-	0.9090	90.90%
CYP1A2 inhibition	-	0.6622	66.22%
CYP2C8 inhibition	-	0.7823	78.23%
CYP inhibitory promiscuity	-	0.8998	89.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.7139	71.39%
Eye corrosion	-	0.9130	91.30%
Eye irritation	+	0.5576	55.76%
Skin irritation	-	0.6823	68.23%
Skin corrosion	-	0.9273	92.73%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6265	62.65%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.7937	79.37%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5378	53.78%
Acute Oral Toxicity (c)	III	0.5204	52.04%
Estrogen receptor binding	+	0.6009	60.09%
Androgen receptor binding	+	0.6191	61.91%
Thyroid receptor binding	+	0.5540	55.40%
Glucocorticoid receptor binding	+	0.5526	55.26%
Aromatase binding	-	0.5239	52.39%
PPAR gamma	+	0.7062	70.62%
Honey bee toxicity	-	0.7809	78.09%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9229	92.29%

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	95.95%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.78%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.58%	99.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.48%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.05%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.75%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.00%	95.89%

Plants that contains it

• Cheirolophus canariensis

Cross-Links

• PubChem: 162996612
• LOTUS: LTS0032747
• wikiData: Q105209016