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

Details

• Internal ID: 09209a31-66fe-4b02-b5c9-5074fee27271
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(CC(C=CC(=O)C(C1OC(=O)C)(C)O)C)OC(=O)C2=C
• SMILES (Isomeric): CCC(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)O)C)OC(=O)C2=C
• InChI: InChI=1S/C22H30O8/c1-7-12(3)20(25)30-18-17-13(4)21(26)29-15(17)10-11(2)8-9-16(24)22(6,27)19(18)28-14(5)23/h8-9,11-12,15,17-19,27H,4,7,10H2,1-3,5-6H3/b9-8-/t11-,12?,15+,17-,18-,19+,22-/m0/s1
• InChI Key: HXRGCHCPNUEBPG-BAFAANROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₈
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.19406791 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.89
• 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	+	0.9837	98.37%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5139	51.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8285	82.85%
OATP1B3 inhibitior	+	0.8744	87.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6039	60.39%
P-glycoprotein inhibitior	+	0.7307	73.07%
P-glycoprotein substrate	-	0.5976	59.76%
CYP3A4 substrate	+	0.6415	64.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9150	91.50%
CYP3A4 inhibition	-	0.6081	60.81%
CYP2C9 inhibition	-	0.8580	85.80%
CYP2C19 inhibition	-	0.8144	81.44%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	-	0.7959	79.59%
CYP2C8 inhibition	-	0.5727	57.27%
CYP inhibitory promiscuity	-	0.8632	86.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9143	91.43%
Carcinogenicity (trinary)	Non-required	0.4464	44.64%
Eye corrosion	-	0.9613	96.13%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.6136	61.36%
Skin corrosion	-	0.9111	91.11%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6392	63.92%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.5709	57.09%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6514	65.14%
Acute Oral Toxicity (c)	III	0.4442	44.42%
Estrogen receptor binding	+	0.7724	77.24%
Androgen receptor binding	+	0.5942	59.42%
Thyroid receptor binding	+	0.5596	55.96%
Glucocorticoid receptor binding	+	0.7766	77.66%
Aromatase binding	+	0.6063	60.63%
PPAR gamma	+	0.6872	68.72%
Honey bee toxicity	-	0.7020	70.20%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9541	95.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.04%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.86%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	96.68%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.35%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.56%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.32%	85.14%
CHEMBL299	P17252	Protein kinase C alpha	93.62%	98.03%
CHEMBL2581	P07339	Cathepsin D	93.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.93%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.52%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.71%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.67%	89.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.97%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.37%	95.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.31%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.32%	97.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.54%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.33%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.28%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.09%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.94%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.78%	94.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.42%	96.47%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.73%	82.50%

Plants that contains it

• Neurolaena oaxacana
• Seriphidium leucodes

Cross-Links

• PubChem: 100963995
• LOTUS: LTS0100594
• wikiData: Q104962527