[(3aR,4R,5R,6R,10R,11R,11aS)-4,10-dihydroxy-6,10-dimethyl-5-(3-methylbutanoyloxy)-3-methylidene-2,9-dioxo-3a,4,5,6,7,8,11,11a-octahydrocyclodeca[b]furan-11-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 90636c61-2e35-4d0d-9b99-737fc8eeb72c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,5R,6R,10R,11R,11aS)-4,10-dihydroxy-6,10-dimethyl-5-(3-methylbutanoyloxy)-3-methylidene-2,9-dioxo-3a,4,5,6,7,8,11,11a-octahydrocyclodeca[b]furan-11-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(C(C(C(CCC(=O)C1(C)O)C)OC(=O)CC(C)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1[C@@H]2[C@@H]([C@H]([C@@H]([C@@H](CCC(=O)[C@]1(C)O)C)OC(=O)CC(C)C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C25H38O9/c1-8-13(4)23(29)34-22-21-18(15(6)24(30)33-21)19(28)20(32-17(27)11-12(2)3)14(5)9-10-16(26)25(22,7)31/h12-14,18-22,28,31H,6,8-11H2,1-5,7H3/t13-,14-,18-,19-,20-,21+,22-,25+/m1/s1
• InChI Key: YRYNHYDOFQYDHO-PHHQLHKISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₈O₉
• Molecular Weight: 482.60 g/mol
• Exact Mass: 482.25158279 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.11
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9779	97.79%
Caco-2	-	0.6967	69.67%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6432	64.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8444	84.44%
OATP1B3 inhibitior	-	0.2648	26.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8677	86.77%
P-glycoprotein inhibitior	+	0.6066	60.66%
P-glycoprotein substrate	-	0.5297	52.97%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8908	89.08%
CYP3A4 inhibition	+	0.6702	67.02%
CYP2C9 inhibition	-	0.5178	51.78%
CYP2C19 inhibition	-	0.5713	57.13%
CYP2D6 inhibition	-	0.9094	90.94%
CYP1A2 inhibition	+	0.5150	51.50%
CYP2C8 inhibition	-	0.5851	58.51%
CYP inhibitory promiscuity	-	0.7280	72.80%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5455	54.55%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9164	91.64%
Skin irritation	+	0.4917	49.17%
Skin corrosion	-	0.8631	86.31%
Ames mutagenesis	-	0.7208	72.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.7674	76.74%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7528	75.28%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5845	58.45%
Acute Oral Toxicity (c)	III	0.4458	44.58%
Estrogen receptor binding	+	0.7603	76.03%
Androgen receptor binding	+	0.6287	62.87%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7301	73.01%
Aromatase binding	+	0.6462	64.62%
PPAR gamma	+	0.6401	64.01%
Honey bee toxicity	-	0.7678	76.78%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9817	98.17%

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	98.36%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.01%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.02%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.22%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	90.84%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.64%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.48%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.01%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.73%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.84%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.27%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.27%	97.14%
CHEMBL299	P17252	Protein kinase C alpha	82.18%	98.03%
CHEMBL5255	O00206	Toll-like receptor 4	81.99%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.72%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.36%	93.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.59%	92.62%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	80.49%	92.26%
CHEMBL4040	P28482	MAP kinase ERK2	80.24%	83.82%

Plants that contains it

• Carpesium triste
• Nerium oleander

Cross-Links

• PubChem: 162996225
• LOTUS: LTS0103860
• wikiData: Q76614149