(7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl) 4-hydroxy-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 58e55053-5bc5-4808-b618-5fab2add5134
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl) 4-hydroxy-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC1=CC(C2C1C3C(C(CC2=C)OC(=O)C(=CCO)CO)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=CC(C2C1C3C(C(CC2=C)OC(=O)C(=CCO)CO)C(=C)C(=O)O3)O
• InChI: InChI=1S/C20H24O7/c1-9-6-13(23)15-10(2)7-14(26-20(25)12(8-22)4-5-21)17-11(3)19(24)27-18(17)16(9)15/h4,6,13-18,21-23H,2-3,5,7-8H2,1H3
• InChI Key: IKJCOTOCIDNGHA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.15220310 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9239	92.39%
Caco-2	-	0.7473	74.73%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6855	68.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8840	88.40%
OATP1B3 inhibitior	+	0.9622	96.22%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7033	70.33%
P-glycoprotein inhibitior	-	0.6478	64.78%
P-glycoprotein substrate	-	0.7021	70.21%
CYP3A4 substrate	+	0.6238	62.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8800	88.00%
CYP3A4 inhibition	-	0.8693	86.93%
CYP2C9 inhibition	-	0.8191	81.91%
CYP2C19 inhibition	-	0.7480	74.80%
CYP2D6 inhibition	-	0.9244	92.44%
CYP1A2 inhibition	-	0.7830	78.30%
CYP2C8 inhibition	-	0.6784	67.84%
CYP inhibitory promiscuity	-	0.7462	74.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5944	59.44%
Eye corrosion	-	0.9572	95.72%
Eye irritation	-	0.8293	82.93%
Skin irritation	-	0.7033	70.33%
Skin corrosion	-	0.8885	88.85%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6862	68.62%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7981	79.81%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6700	67.00%
Acute Oral Toxicity (c)	III	0.4332	43.32%
Estrogen receptor binding	+	0.7402	74.02%
Androgen receptor binding	+	0.5267	52.67%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6135	61.35%
Aromatase binding	+	0.5495	54.95%
PPAR gamma	-	0.5417	54.17%
Honey bee toxicity	-	0.7293	72.93%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9136	91.36%

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	94.75%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.30%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.78%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.91%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.82%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.30%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	83.73%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.09%	99.23%
CHEMBL2581	P07339	Cathepsin D	82.36%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.29%	89.00%

Plants that contains it

• Chaenactis douglasii
• Eupatorium altissimum

Cross-Links

• PubChem: 162846449
• LOTUS: LTS0025713
• wikiData: Q105114678