[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3aR,5E,7S,9Z,11aS)-7-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-10-carboxylate

Details

• Internal ID: 3eb5d106-95fa-4234-886c-4b19f3af062e
• 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] (3aR,5E,7S,9Z,11aS)-7-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-10-carboxylate
• SMILES (Canonical): CC1=CCC2C(CC(=CCC1O)C(=O)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C2=C
• SMILES (Isomeric): C/C/1=C\C[C@H]2[C@H](C/C(=C/C[C@@H]1O)/C(=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C2=C
• InChI: InChI=1S/C21H28O10/c1-9-3-5-12-10(2)19(27)29-14(12)7-11(4-6-13(9)23)20(28)31-21-18(26)17(25)16(24)15(8-22)30-21/h3-4,12-18,21-26H,2,5-8H2,1H3/b9-3+,11-4-/t12-,13+,14+,15-,16-,17+,18-,21+/m1/s1
• InChI Key: MUYHZEOCHWIVHX-YMJCGVMBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₁₀
• Molecular Weight: 440.40 g/mol
• Exact Mass: 440.16824709 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.16
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7384	73.84%
Caco-2	-	0.8453	84.53%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7588	75.88%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.8222	82.22%
OATP1B3 inhibitior	+	0.9680	96.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5940	59.40%
P-glycoprotein inhibitior	-	0.7201	72.01%
P-glycoprotein substrate	-	0.8097	80.97%
CYP3A4 substrate	+	0.6248	62.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.9304	93.04%
CYP2C9 inhibition	-	0.9204	92.04%
CYP2C19 inhibition	-	0.8991	89.91%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.8653	86.53%
CYP2C8 inhibition	+	0.4483	44.83%
CYP inhibitory promiscuity	-	0.9489	94.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7462	74.62%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9415	94.15%
Skin irritation	-	0.7205	72.05%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6684	66.84%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6694	66.94%
skin sensitisation	-	0.8730	87.30%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6218	62.18%
Acute Oral Toxicity (c)	III	0.4732	47.32%
Estrogen receptor binding	+	0.7746	77.46%
Androgen receptor binding	+	0.5516	55.16%
Thyroid receptor binding	-	0.5617	56.17%
Glucocorticoid receptor binding	+	0.5961	59.61%
Aromatase binding	+	0.5949	59.49%
PPAR gamma	+	0.6384	63.84%
Honey bee toxicity	-	0.7906	79.06%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9403	94.03%

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	94.05%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	91.61%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.08%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.85%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.70%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.31%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.22%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.56%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.91%	91.24%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.79%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	85.32%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.46%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.26%	97.25%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.03%	96.37%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.16%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.58%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.64%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.95%	93.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.50%	93.56%
CHEMBL5255	O00206	Toll-like receptor 4	80.13%	92.50%

Plants that contains it

• Pertya glabrescens

Cross-Links

• PubChem: 163074510
• LOTUS: LTS0081622
• wikiData: Q105172816