[(3aS,4S,5R,6S,8Z,10R,11aR)-5-[(E)-but-2-enoyl]oxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-but-2-enoate

Details

• Internal ID: 61beaa40-89b2-4094-80ca-a4710973ce70
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4S,5R,6S,8Z,10R,11aR)-5-[(E)-but-2-enoyl]oxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-but-2-enoate
• SMILES (Canonical): CC=CC(=O)OC1C2C(CC(C=CC(=O)C(C1OC(=O)C=CC)(C)O)C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C/C(=O)O[C@H]1[C@@H]2[C@@H](C[C@H](/C=C\C(=O)[C@@]([C@@H]1OC(=O)/C=C/C)(C)O)C)OC(=O)C2=C
• InChI: InChI=1S/C23H28O8/c1-6-8-17(25)30-20-19-14(4)22(27)29-15(19)12-13(3)10-11-16(24)23(5,28)21(20)31-18(26)9-7-2/h6-11,13,15,19-21,28H,4,12H2,1-3,5H3/b8-6+,9-7+,11-10-/t13-,15+,19-,20-,21+,23+/m0/s1
• InChI Key: FUUOEHIVTNGEJJ-FOHKJMSUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₈
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.17841785 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 8
• 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	+	0.9773	97.73%
Caco-2	+	0.5493	54.93%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5813	58.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8432	84.32%
OATP1B3 inhibitior	+	0.8770	87.70%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6153	61.53%
P-glycoprotein inhibitior	+	0.7075	70.75%
P-glycoprotein substrate	-	0.6945	69.45%
CYP3A4 substrate	+	0.6493	64.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9134	91.34%
CYP3A4 inhibition	-	0.7157	71.57%
CYP2C9 inhibition	-	0.9348	93.48%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	-	0.8045	80.45%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9352	93.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.4138	41.38%
Eye corrosion	-	0.9516	95.16%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.6237	62.37%
Skin corrosion	-	0.9112	91.12%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6741	67.41%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.5977	59.77%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6210	62.10%
Acute Oral Toxicity (c)	III	0.3571	35.71%
Estrogen receptor binding	+	0.7498	74.98%
Androgen receptor binding	-	0.5078	50.78%
Thyroid receptor binding	+	0.5791	57.91%
Glucocorticoid receptor binding	+	0.7445	74.45%
Aromatase binding	-	0.5557	55.57%
PPAR gamma	+	0.6101	61.01%
Honey bee toxicity	-	0.6823	68.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9373	93.73%

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	98.19%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.82%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.84%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.09%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.76%	91.07%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.67%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.32%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.25%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	87.17%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	86.35%	98.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.12%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.68%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.52%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.51%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	83.72%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.24%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.91%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	80.47%	90.17%
CHEMBL4208	P20618	Proteasome component C5	80.23%	90.00%

Plants that contains it

• Calea urticifolia

Cross-Links

• PubChem: 162952969
• LOTUS: LTS0000271
• wikiData: Q105002054