[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,3aS,6Z,10E,11aS)-3,10-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-6-carboxylate

Details

• Internal ID: e455f7f6-a067-46ec-b582-4d3f2ed1e166
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,3aS,6Z,10E,11aS)-3,10-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CC1C2CCC(=CCCC(=CC2OC1=O)C)C(=O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC/C(=C/CC/C(=C/[C@H]2OC1=O)/C)/C(=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C21H30O9/c1-10-4-3-5-12(6-7-13-11(2)19(26)28-14(13)8-10)20(27)30-21-18(25)17(24)16(23)15(9-22)29-21/h5,8,11,13-18,21-25H,3-4,6-7,9H2,1-2H3/b10-8+,12-5-/t11-,13-,14+,15+,16+,17-,18+,21-/m0/s1
• InChI Key: MZHAVSOJYFEDBV-YUSNIWGTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₉
• Molecular Weight: 426.50 g/mol
• Exact Mass: 426.18898253 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7222	72.22%
Caco-2	-	0.7857	78.57%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8662	86.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8609	86.09%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7030	70.30%
P-glycoprotein inhibitior	-	0.7418	74.18%
P-glycoprotein substrate	-	0.7918	79.18%
CYP3A4 substrate	+	0.6501	65.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.8331	83.31%
CYP2C9 inhibition	-	0.8927	89.27%
CYP2C19 inhibition	-	0.9082	90.82%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.7293	72.93%
CYP2C8 inhibition	-	0.7023	70.23%
CYP inhibitory promiscuity	-	0.9106	91.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7065	70.65%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9715	97.15%
Skin irritation	-	0.6514	65.14%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.7132	71.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.8377	83.77%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9126	91.26%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7960	79.60%
Acute Oral Toxicity (c)	III	0.4468	44.68%
Estrogen receptor binding	+	0.5793	57.93%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6454	64.54%
Glucocorticoid receptor binding	-	0.5872	58.72%
Aromatase binding	-	0.6552	65.52%
PPAR gamma	-	0.5926	59.26%
Honey bee toxicity	-	0.8156	81.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9578	95.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.47%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.02%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.30%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.18%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	87.90%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.21%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.35%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	85.01%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.15%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.43%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.83%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.16%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.39%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.16%	86.33%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.14%	90.93%

Plants that contains it

• Taraxacum erythrospermum
• Taraxacum obovatum
• Taraxacum officinale
• Taraxacum platycarpum subsp. hondoense

Cross-Links

• PubChem: 163051458
• LOTUS: LTS0069676
• wikiData: Q105175477