4-(4-Hydroxy-2-methylbut-2-enoyl)oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylic acid

Details

• Internal ID: 7f002e76-164e-4697-9f99-08e482133d0b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: 4-(4-hydroxy-2-methylbut-2-enoyl)oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylic acid
• SMILES (Canonical): CC1=CC2C(C(CC(=CCC1)C(=O)O)OC(=O)C(=CCO)C)C(=C)C(=O)O2
• SMILES (Isomeric): CC1=CC2C(C(CC(=CCC1)C(=O)O)OC(=O)C(=CCO)C)C(=C)C(=O)O2
• InChI: InChI=1S/C20H24O7/c1-11-5-4-6-14(18(22)23)10-16(26-19(24)12(2)7-8-21)17-13(3)20(25)27-15(17)9-11/h6-7,9,15-17,21H,3-5,8,10H2,1-2H3,(H,22,23)
• InChI Key: UPMNFYNIENFBCT-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): 110.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9712	97.12%
Caco-2	-	0.5503	55.03%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7923	79.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7320	73.20%
BSEP inhibitior	-	0.6123	61.23%
P-glycoprotein inhibitior	-	0.5673	56.73%
P-glycoprotein substrate	-	0.7897	78.97%
CYP3A4 substrate	+	0.6000	60.00%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.9127	91.27%
CYP3A4 inhibition	-	0.6122	61.22%
CYP2C9 inhibition	-	0.8680	86.80%
CYP2C19 inhibition	-	0.8737	87.37%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.5854	58.54%
CYP inhibitory promiscuity	-	0.8553	85.53%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7124	71.24%
Eye corrosion	-	0.9781	97.81%
Eye irritation	-	0.8607	86.07%
Skin irritation	-	0.6844	68.44%
Skin corrosion	-	0.9436	94.36%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5725	57.25%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5016	50.16%
skin sensitisation	-	0.8911	89.11%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5595	55.95%
Acute Oral Toxicity (c)	III	0.4018	40.18%
Estrogen receptor binding	+	0.5608	56.08%
Androgen receptor binding	+	0.5316	53.16%
Thyroid receptor binding	-	0.5815	58.15%
Glucocorticoid receptor binding	+	0.5393	53.93%
Aromatase binding	-	0.5419	54.19%
PPAR gamma	-	0.4830	48.30%
Honey bee toxicity	-	0.7032	70.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9879	98.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.19%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.73%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.20%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.86%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.94%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.89%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.69%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.86%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.77%	93.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.80%	93.56%

Plants that contains it

• Stevia aristata

Cross-Links

• PubChem: 163069803
• LOTUS: LTS0093241
• wikiData: Q105276873