[(1S,2R,4S,5R,6S,7R,8S,9R,12R)-8,12-diacetyloxy-5,7-dibenzoyloxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-4-yl] pyridine-3-carboxylate

Details

• Internal ID: 4a19a6e5-00ac-442c-9f26-ab44a0d26518
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(1S,2R,4S,5R,6S,7R,8S,9R,12R)-8,12-diacetyloxy-5,7-dibenzoyloxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-4-yl] pyridine-3-carboxylate
• SMILES (Canonical): CC1CC(C(C2(C13C(C(C(C2OC(=O)C4=CC=CC=C4)OC(=O)C)C(O3)(C)C)OC(=O)C)C)OC(=O)C5=CC=CC=C5)OC(=O)C6=CN=CC=C6
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@H]([C@@]2([C@]13[C@@H]([C@@H]([C@@H]([C@@H]2OC(=O)C4=CC=CC=C4)OC(=O)C)C(O3)(C)C)OC(=O)C)C)OC(=O)C5=CC=CC=C5)OC(=O)C6=CN=CC=C6
• InChI: InChI=1S/C39H41NO11/c1-22-20-28(48-36(45)27-18-13-19-40-21-27)31(49-34(43)25-14-9-7-10-15-25)38(6)33(50-35(44)26-16-11-8-12-17-26)30(46-23(2)41)29-32(47-24(3)42)39(22,38)51-37(29,4)5/h7-19,21-22,28-33H,20H2,1-6H3/t22-,28+,29-,30+,31+,32-,33+,38+,39-/m1/s1
• InChI Key: BQVGZDYZYXCBOZ-IPGGTLSNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₁NO₁₁
• Molecular Weight: 699.70 g/mol
• Exact Mass: 699.26796112 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.15
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• BDBM50221853
• nicotinic acid (1S,2R,4S,5R,6S,7R,8S,9R,12R)-8,12-diacetoxy-5,7-bis-benzoyloxy-2,6,10,10-tetramethyl-11-oxa-tricyclo[7.2.1.0*1,6*]dodec-4-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9558	95.58%
Caco-2	-	0.7747	77.47%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5995	59.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8786	87.86%
OATP1B3 inhibitior	+	0.9141	91.41%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9959	99.59%
P-glycoprotein inhibitior	+	0.9350	93.50%
P-glycoprotein substrate	-	0.6375	63.75%
CYP3A4 substrate	+	0.6358	63.58%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8656	86.56%
CYP3A4 inhibition	+	0.5461	54.61%
CYP2C9 inhibition	-	0.8608	86.08%
CYP2C19 inhibition	-	0.6439	64.39%
CYP2D6 inhibition	-	0.9177	91.77%
CYP1A2 inhibition	-	0.6805	68.05%
CYP2C8 inhibition	+	0.7846	78.46%
CYP inhibitory promiscuity	-	0.7035	70.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4119	41.19%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8939	89.39%
Skin irritation	-	0.8181	81.81%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8529	85.29%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8074	80.74%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5760	57.60%
Acute Oral Toxicity (c)	III	0.5529	55.29%
Estrogen receptor binding	+	0.7983	79.83%
Androgen receptor binding	+	0.6319	63.19%
Thyroid receptor binding	+	0.7205	72.05%
Glucocorticoid receptor binding	+	0.7663	76.63%
Aromatase binding	+	0.6032	60.32%
PPAR gamma	+	0.7590	75.90%
Honey bee toxicity	-	0.8030	80.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5045	50.45%
Fish aquatic toxicity	+	0.8898	88.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4302	P08183	P-glycoprotein 1	7762.47 nM; 7720 nM	Ki; Ki	PMID: 17850057; PMID: 17850057

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2996	Q05655	Protein kinase C delta	97.25%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.72%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.72%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.84%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.88%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.70%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.61%	94.62%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.41%	81.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.16%	94.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.89%	91.11%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.01%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	88.28%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	86.89%	90.17%
CHEMBL5028	O14672	ADAM10	85.51%	97.50%
CHEMBL4208	P20618	Proteasome component C5	82.57%	90.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.46%	93.10%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.74%	89.44%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.70%	91.07%

Plants that contains it

• Bupleurum falcatum
• Magnolia officinalis
• Stemona tuberosa

Cross-Links

• PubChem: 10887010
• NPASS: NPC158020
• ChEMBL: CHEMBL411882