[7-Hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 3,4-dihydroxy-2-methylidenebutanoate

Details

• Internal ID: 68dcdc80-2095-4c56-a9d0-93f95a65f444
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 3,4-dihydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1=C(CCC(=CC2C(C(C1)OC(=O)C(=C)C(CO)O)C(=C)C(=O)O2)CO)O
• SMILES (Isomeric): CC1=C(CCC(=CC2C(C(C1)OC(=O)C(=C)C(CO)O)C(=C)C(=O)O2)CO)O
• InChI: InChI=1S/C20H26O8/c1-10-6-16(27-19(25)11(2)15(24)9-22)18-12(3)20(26)28-17(18)7-13(8-21)4-5-14(10)23/h7,15-18,21-24H,2-6,8-9H2,1H3
• InChI Key: YXSRKMIQVUZBKW-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.16276778 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9020	90.20%
Caco-2	-	0.7743	77.43%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7668	76.68%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9567	95.67%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8548	85.48%
P-glycoprotein inhibitior	-	0.7689	76.89%
P-glycoprotein substrate	-	0.5375	53.75%
CYP3A4 substrate	+	0.6290	62.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8762	87.62%
CYP3A4 inhibition	-	0.7494	74.94%
CYP2C9 inhibition	-	0.8548	85.48%
CYP2C19 inhibition	-	0.8106	81.06%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.6146	61.46%
CYP2C8 inhibition	-	0.5712	57.12%
CYP inhibitory promiscuity	-	0.9643	96.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6746	67.46%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8029	80.29%
Skin irritation	-	0.6097	60.97%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6002	60.02%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9121	91.21%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5917	59.17%
Acute Oral Toxicity (c)	III	0.5169	51.69%
Estrogen receptor binding	+	0.6575	65.75%
Androgen receptor binding	+	0.5948	59.48%
Thyroid receptor binding	-	0.6038	60.38%
Glucocorticoid receptor binding	+	0.6719	67.19%
Aromatase binding	+	0.6241	62.41%
PPAR gamma	+	0.5776	57.76%
Honey bee toxicity	-	0.7555	75.55%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9709	97.09%

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	97.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.15%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.61%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.22%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.22%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.83%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.27%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	83.07%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.09%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.56%	97.25%

Plants that contains it

• Centaurea spinosa

Cross-Links

• PubChem: 162910468
• LOTUS: LTS0000842
• wikiData: Q105368124