[(3aR,4R,6E,9S,10Z,11aS)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-3-methylbut-2-enoate

Details

• Internal ID: f2d54d42-283c-4357-ab1a-577eed997824
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,9S,10Z,11aS)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-3-methylbut-2-enoate
• InChI: InChI=1S/C22H28O7/c1-12-6-7-17(27-16(5)24)14(3)10-19-21(15(4)22(26)29-19)18(8-12)28-20(25)9-13(2)11-23/h6,9-10,17-19,21,23H,4,7-8,11H2,1-3,5H3/b12-6+,13-9+,14-10-/t17-,18+,19-,21+/m0/s1
• InChI Key: WEDSOCSUZTUNGQ-NDCHMDHSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.18350323 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.5345	53.45%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6172	61.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8425	84.25%
P-glycoprotein inhibitior	+	0.7208	72.08%
P-glycoprotein substrate	-	0.5589	55.89%
CYP3A4 substrate	+	0.6536	65.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8459	84.59%
CYP2C19 inhibition	-	0.8430	84.30%
CYP2D6 inhibition	-	0.9525	95.25%
CYP1A2 inhibition	-	0.5470	54.70%
CYP2C8 inhibition	-	0.5828	58.28%
CYP inhibitory promiscuity	-	0.8914	89.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6262	62.62%
Eye corrosion	-	0.9695	96.95%
Eye irritation	-	0.8532	85.32%
Skin irritation	-	0.5930	59.30%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4026	40.26%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.7802	78.02%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6805	68.05%
Acute Oral Toxicity (c)	III	0.5004	50.04%
Estrogen receptor binding	+	0.7414	74.14%
Androgen receptor binding	-	0.5108	51.08%
Thyroid receptor binding	+	0.5204	52.04%
Glucocorticoid receptor binding	+	0.8126	81.26%
Aromatase binding	-	0.5085	50.85%
PPAR gamma	+	0.5309	53.09%
Honey bee toxicity	-	0.6465	64.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9791	97.91%

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	97.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.03%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.72%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.10%	94.73%
CHEMBL4040	P28482	MAP kinase ERK2	86.46%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.39%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.53%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.12%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.17%	97.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.04%	91.19%

Plants that contains it

• Schkuhria pinnata

Cross-Links

• PubChem: 162880208
• LOTUS: LTS0001654
• wikiData: Q105302917