[(1R,3R,4S,4aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-3,3a,4,6a-tetrahydro-2H-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate

Details

• Internal ID: 5853e3b0-a9b7-4582-bd8f-dda6f95ea3f5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,3R,4S,4aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-3,3a,4,6a-tetrahydro-2H-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
• SMILES (Canonical): CC1=CCCC2C1(C(C(C(C2(C)C3CC4COC(=O)C4O3)(C)O)O)OC(=O)C5=CN=CC=C5)C
• SMILES (Isomeric): CC1=CCC[C@H]2C1([C@H](C([C@]([C@]2(C)[C@@H]3CC4COC(=O)C4O3)(C)O)O)OC(=O)C5=CN=CC=C5)C
• InChI: InChI=1S/C26H33NO7/c1-14-7-5-9-17-24(14,2)21(34-22(29)15-8-6-10-27-12-15)20(28)26(4,31)25(17,3)18-11-16-13-32-23(30)19(16)33-18/h6-8,10,12,16-21,28,31H,5,9,11,13H2,1-4H3/t16?,17-,18-,19?,20?,21-,24?,25-,26-/m0/s1
• InChI Key: KDECGZYJLPCSOX-LVVRMGBLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₃NO₇
• Molecular Weight: 471.50 g/mol
• Exact Mass: 471.22570239 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 960302-92-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9077	90.77%
Caco-2	-	0.7265	72.65%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8303	83.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8848	88.48%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9603	96.03%
P-glycoprotein inhibitior	+	0.6114	61.14%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.7690	76.90%
CYP2C9 inhibition	-	0.8270	82.70%
CYP2C19 inhibition	-	0.8375	83.75%
CYP2D6 inhibition	-	0.9296	92.96%
CYP1A2 inhibition	-	0.5789	57.89%
CYP2C8 inhibition	+	0.7538	75.38%
CYP inhibitory promiscuity	-	0.6730	67.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4611	46.11%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9505	95.05%
Skin irritation	-	0.7083	70.83%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	+	0.5274	52.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.4037	40.37%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5301	53.01%
skin sensitisation	-	0.8513	85.13%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.4618	46.18%
Acute Oral Toxicity (c)	III	0.3607	36.07%
Estrogen receptor binding	+	0.8105	81.05%
Androgen receptor binding	+	0.6546	65.46%
Thyroid receptor binding	+	0.5679	56.79%
Glucocorticoid receptor binding	+	0.7809	78.09%
Aromatase binding	+	0.8059	80.59%
PPAR gamma	+	0.5693	56.93%
Honey bee toxicity	-	0.8015	80.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9160	91.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.66%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.28%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	92.49%	97.79%
CHEMBL2179	P04062	Beta-glucocerebrosidase	92.00%	85.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.17%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.86%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	89.86%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.24%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.22%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.09%	89.00%
CHEMBL4208	P20618	Proteasome component C5	88.03%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.49%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.48%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.66%	100.00%
CHEMBL2535	P11166	Glucose transporter	86.21%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.21%	91.07%
CHEMBL5028	O14672	ADAM10	84.44%	97.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.17%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.49%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.42%	96.77%

Plants that contains it

• Scutellaria barbata

Cross-Links

• PubChem: 101844351
• NPASS: NPC31048