[(2R,3S,4S,5R,6R)-6-[(4S)-5-[(3aR,4R,5R,6aR)-5-hydroxy-5-methyl-3-methylidene-2-oxo-3a,4,6,6a-tetrahydrocyclopenta[b]furan-4-yl]-4-methyl-5-oxopentoxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 2d195500-bdfa-40f0-a1ad-feb97302727c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[(4S)-5-[(3aR,4R,5R,6aR)-5-hydroxy-5-methyl-3-methylidene-2-oxo-3a,4,6,6a-tetrahydrocyclopenta[b]furan-4-yl]-4-methyl-5-oxopentoxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(CCCOC1C(C(C(C(O1)COC(=O)C)O)O)O)C(=O)C2C3C(CC2(C)O)OC(=O)C3=C
• SMILES (Isomeric): C[C@@H](CCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)O)O)O)C(=O)[C@@H]2[C@H]3[C@@H](C[C@@]2(C)O)OC(=O)C3=C
• InChI: InChI=1S/C23H34O11/c1-10(17(25)16-15-11(2)21(29)33-13(15)8-23(16,4)30)6-5-7-31-22-20(28)19(27)18(26)14(34-22)9-32-12(3)24/h10,13-16,18-20,22,26-28,30H,2,5-9H2,1,3-4H3/t10-,13+,14+,15+,16-,18+,19-,20+,22+,23+/m0/s1
• InChI Key: DVXWVFXAXIIFHO-LZMFOXHKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₁₁
• Molecular Weight: 486.50 g/mol
• Exact Mass: 486.21011190 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.77
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7014	70.14%
Caco-2	-	0.8264	82.64%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7361	73.61%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.8693	86.93%
OATP1B3 inhibitior	+	0.9205	92.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	-	0.8147	81.47%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.6668	66.68%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9035	90.35%
CYP3A4 inhibition	-	0.8448	84.48%
CYP2C9 inhibition	-	0.8460	84.60%
CYP2C19 inhibition	-	0.8835	88.35%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.8647	86.47%
CYP2C8 inhibition	-	0.6351	63.51%
CYP inhibitory promiscuity	-	0.9430	94.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5763	57.63%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.5233	52.33%
Skin corrosion	-	0.9057	90.57%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4199	41.99%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8695	86.95%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6075	60.75%
Acute Oral Toxicity (c)	III	0.5524	55.24%
Estrogen receptor binding	+	0.7291	72.91%
Androgen receptor binding	+	0.5784	57.84%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6223	62.23%
Aromatase binding	-	0.4853	48.53%
PPAR gamma	+	0.5212	52.12%
Honey bee toxicity	-	0.7655	76.55%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9004	90.04%

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	97.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.59%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.79%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.32%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.77%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.62%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.26%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.19%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.57%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.78%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.00%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.75%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.50%	93.56%
CHEMBL2996	Q05655	Protein kinase C delta	82.06%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	81.86%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.48%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.84%	89.34%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.72%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.21%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.09%	95.56%

Plants that contains it

• Picradeniopsis woodhousei

Cross-Links

• PubChem: 162970988
• LOTUS: LTS0166845
• wikiData: Q104990420