[(1S,2S,5S,6S,7S,9R,12R)-5-benzoyloxy-2-hydroxy-2,6,10,10-tetramethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-12-yl] pyridine-3-carboxylate

Details

• Internal ID: ed99fa27-2f76-473d-9589-09a85c06356b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Agarofurans
• IUPAC Name: [(1S,2S,5S,6S,7S,9R,12R)-5-benzoyloxy-2-hydroxy-2,6,10,10-tetramethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-12-yl] pyridine-3-carboxylate
• SMILES (Canonical): CC1(C2CC(C3(C(CCC(C3(C2OC(=O)C4=CN=CC=C4)O1)(C)O)OC(=O)C5=CC=CC=C5)C)OC(=O)C=CC6=CC=CC=C6)C
• SMILES (Isomeric): C[C@@]1(CC[C@@H]([C@@]2([C@]13[C@@H]([C@@H](C[C@@H]2OC(=O)/C=C/C4=CC=CC=C4)C(O3)(C)C)OC(=O)C5=CN=CC=C5)C)OC(=O)C6=CC=CC=C6)O
• InChI: InChI=1S/C37H39NO8/c1-34(2)27-22-29(43-30(39)18-17-24-12-7-5-8-13-24)36(4)28(44-32(40)25-14-9-6-10-15-25)19-20-35(3,42)37(36,46-34)31(27)45-33(41)26-16-11-21-38-23-26/h5-18,21,23,27-29,31,42H,19-20,22H2,1-4H3/b18-17+/t27-,28+,29+,31-,35+,36+,37+/m1/s1
• InChI Key: WQWQXHJOHCKMLS-APSUIMNOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₃₉NO₈
• Molecular Weight: 625.70 g/mol
• Exact Mass: 625.26756720 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.58
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9773	97.73%
Caco-2	-	0.7926	79.26%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6784	67.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8710	87.10%
OATP1B3 inhibitior	-	0.2855	28.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9887	98.87%
P-glycoprotein inhibitior	+	0.9002	90.02%
P-glycoprotein substrate	-	0.5443	54.43%
CYP3A4 substrate	+	0.6764	67.64%
CYP2C9 substrate	-	0.7940	79.40%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	+	0.6042	60.42%
CYP2C9 inhibition	-	0.8770	87.70%
CYP2C19 inhibition	-	0.8282	82.82%
CYP2D6 inhibition	-	0.9383	93.83%
CYP1A2 inhibition	-	0.7156	71.56%
CYP2C8 inhibition	+	0.9271	92.71%
CYP inhibitory promiscuity	-	0.9119	91.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4815	48.15%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.7238	72.38%
Skin corrosion	-	0.9031	90.31%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.9187	91.87%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5367	53.67%
skin sensitisation	-	0.8279	82.79%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7965	79.65%
Acute Oral Toxicity (c)	III	0.4853	48.53%
Estrogen receptor binding	+	0.7653	76.53%
Androgen receptor binding	+	0.7127	71.27%
Thyroid receptor binding	+	0.6875	68.75%
Glucocorticoid receptor binding	+	0.7780	77.80%
Aromatase binding	+	0.6262	62.62%
PPAR gamma	+	0.6855	68.55%
Honey bee toxicity	-	0.8119	81.19%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.9594	95.94%

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	97.89%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.87%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.53%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.55%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.44%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.04%	89.34%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	88.88%	89.44%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.96%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.91%	91.07%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.70%	85.14%
CHEMBL5028	O14672	ADAM10	86.68%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.32%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.10%	94.08%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.86%	83.00%
CHEMBL2996	Q05655	Protein kinase C delta	85.15%	97.79%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	84.82%	92.86%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.70%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.63%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.21%	85.31%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.91%	81.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.85%	89.00%
CHEMBL2535	P11166	Glucose transporter	83.77%	98.75%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.71%	97.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.46%	93.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	82.70%	95.71%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	82.02%	96.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.91%	92.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.80%	90.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.07%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.62%	94.62%

Plants that contains it

• Tripterygium wilfordii

Cross-Links

• PubChem: 57333432
• NPASS: NPC9368