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

Details

• Internal ID: 8760c80d-6278-41f3-b3d5-7bd87c459807
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (6E,10Z)-10-methyl-4-[(E)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CCCC(=CC2C1C(=C)C(=O)O2)C)C(=O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)OC1C/C(=C\CC/C(=C\C2C1C(=C)C(=O)O2)/C)/C(=O)O
• InChI: InChI=1S/C20H24O6/c1-5-12(3)19(23)25-16-10-14(18(21)22)8-6-7-11(2)9-15-17(16)13(4)20(24)26-15/h5,8-9,15-17H,4,6-7,10H2,1-3H3,(H,21,22)/b11-9-,12-5+,14-8+
• InChI Key: IOPBGRHISQTQKP-KODVERRDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 956384-55-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	+	0.5895	58.95%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7110	71.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.8346	83.46%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	+	0.6280	62.80%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8320	83.20%
CYP3A4 substrate	+	0.5899	58.99%
CYP2C9 substrate	-	0.5981	59.81%
CYP2D6 substrate	-	0.9178	91.78%
CYP3A4 inhibition	-	0.7016	70.16%
CYP2C9 inhibition	-	0.8390	83.90%
CYP2C19 inhibition	-	0.7812	78.12%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	+	0.6865	68.65%
CYP2C8 inhibition	-	0.6207	62.07%
CYP inhibitory promiscuity	-	0.9324	93.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6532	65.32%
Eye corrosion	-	0.9607	96.07%
Eye irritation	-	0.8737	87.37%
Skin irritation	-	0.5932	59.32%
Skin corrosion	-	0.9333	93.33%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5215	52.15%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.7141	71.41%
skin sensitisation	-	0.8143	81.43%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7277	72.77%
Acute Oral Toxicity (c)	II	0.4588	45.88%
Estrogen receptor binding	-	0.5104	51.04%
Androgen receptor binding	+	0.5304	53.04%
Thyroid receptor binding	-	0.5385	53.85%
Glucocorticoid receptor binding	+	0.5990	59.90%
Aromatase binding	-	0.7141	71.41%
PPAR gamma	-	0.4866	48.66%
Honey bee toxicity	-	0.6269	62.69%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.84%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.00%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.38%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.99%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.23%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	84.06%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.26%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.91%	89.00%

Plants that contains it

• Pentanema germanicum

Cross-Links

• PubChem: 90473376
• LOTUS: LTS0063246
• wikiData: Q105116800