[10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] 4-hydroxy-2-methylidenebutanoate

Details

• Internal ID: 99cbbb64-6014-442a-a27b-8130d127b801
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] 4-hydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2OC1=O)CO)C)OC(=O)C(=C)CCO
• SMILES (Isomeric): CC1C2C(CC(=CCCC(=CC2OC1=O)CO)C)OC(=O)C(=C)CCO
• InChI: InChI=1S/C20H28O6/c1-12-5-4-6-15(11-22)10-17-18(14(3)20(24)26-17)16(9-12)25-19(23)13(2)7-8-21/h5,10,14,16-18,21-22H,2,4,6-9,11H2,1,3H3
• InChI Key: DTSRWZQRWMWHDL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 6
• 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	+	0.9588	95.88%
Caco-2	+	0.5377	53.77%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7495	74.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8950	89.50%
OATP1B3 inhibitior	+	0.9562	95.62%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.7070	70.70%
BSEP inhibitior	-	0.5831	58.31%
P-glycoprotein inhibitior	-	0.7205	72.05%
P-glycoprotein substrate	-	0.6173	61.73%
CYP3A4 substrate	+	0.6260	62.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8889	88.89%
CYP3A4 inhibition	+	0.5412	54.12%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.8785	87.85%
CYP2D6 inhibition	-	0.9187	91.87%
CYP1A2 inhibition	-	0.5972	59.72%
CYP2C8 inhibition	-	0.6999	69.99%
CYP inhibitory promiscuity	-	0.9223	92.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6827	68.27%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.6368	63.68%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.5082	50.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.5752	57.52%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9048	90.48%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7196	71.96%
Acute Oral Toxicity (c)	III	0.4498	44.98%
Estrogen receptor binding	-	0.5730	57.30%
Androgen receptor binding	-	0.5224	52.24%
Thyroid receptor binding	-	0.6292	62.92%
Glucocorticoid receptor binding	+	0.5954	59.54%
Aromatase binding	+	0.5646	56.46%
PPAR gamma	-	0.5895	58.95%
Honey bee toxicity	-	0.8152	81.52%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9792	97.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.39%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.81%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.50%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.51%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.97%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.27%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.66%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.23%	89.00%

Plants that contains it

• Centaurea pullata

Cross-Links

• PubChem: 74218927
• LOTUS: LTS0238473
• wikiData: Q104989002