[(1S,2R,4S,5R,6R,7S,9R,12R)-4,5,12-triacetyloxy-6-(acetyloxymethyl)-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate

Details

• Internal ID: 18bcbcc2-9387-43c0-a371-36f49032ba6f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(1S,2R,4S,5R,6R,7S,9R,12R)-4,5,12-triacetyloxy-6-(acetyloxymethyl)-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate
• SMILES (Canonical): CC1CC(C(C2(C13C(C(CC2OC(=O)C4=CC=CC=C4)C(O3)(C)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@H]([C@@]2([C@]13[C@@H]([C@@H](C[C@@H]2OC(=O)C4=CC=CC=C4)C(O3)(C)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C30H38O11/c1-16-13-23(37-18(3)32)26(39-20(5)34)29(15-36-17(2)31)24(40-27(35)21-11-9-8-10-12-21)14-22-25(38-19(4)33)30(16,29)41-28(22,6)7/h8-12,16,22-26H,13-15H2,1-7H3/t16-,22-,23+,24+,25-,26+,29-,30-/m1/s1
• InChI Key: PBBYYGCXAHKQFJ-YLMNRMNTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₁
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.24141202 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• C30H38O11
• BDBM50169030
• Benzoic acid (1S,2R,4S,5R,6R,7S,9R,12R)-4,5,12-triacetoxy-6-acetoxymethyl-2,10,10-trimethyl-11-oxa-tricyclo[7.2.1.0*1,6*]dodec-7-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	-	0.6650	66.50%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7201	72.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8794	87.94%
OATP1B3 inhibitior	+	0.9147	91.47%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8298	82.98%
P-glycoprotein inhibitior	+	0.8909	89.09%
P-glycoprotein substrate	-	0.6369	63.69%
CYP3A4 substrate	+	0.6597	65.97%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8529	85.29%
CYP3A4 inhibition	-	0.7333	73.33%
CYP2C9 inhibition	-	0.5496	54.96%
CYP2C19 inhibition	-	0.5618	56.18%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.7861	78.61%
CYP2C8 inhibition	+	0.7105	71.05%
CYP inhibitory promiscuity	-	0.7371	73.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5895	58.95%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8682	86.82%
Skin irritation	-	0.8053	80.53%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8059	80.59%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8106	81.06%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4813	48.13%
Acute Oral Toxicity (c)	III	0.4882	48.82%
Estrogen receptor binding	+	0.8776	87.76%
Androgen receptor binding	+	0.6555	65.55%
Thyroid receptor binding	+	0.6725	67.25%
Glucocorticoid receptor binding	+	0.7438	74.38%
Aromatase binding	+	0.5933	59.33%
PPAR gamma	+	0.7503	75.03%
Honey bee toxicity	-	0.8167	81.67%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.9971	99.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4302	P08183	P-glycoprotein 1	2360 nM; 2344.23 nM	Ki; Ki	PMID: 17850057; PMID: 17850057

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.63%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.58%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	96.22%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	93.79%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.88%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.92%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.74%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.22%	97.09%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	87.16%	91.65%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.52%	95.56%
CHEMBL5028	O14672	ADAM10	84.91%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.89%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.92%	81.11%
CHEMBL340	P08684	Cytochrome P450 3A4	82.03%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.32%	97.14%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.98%	83.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.07%	97.25%

Plants that contains it

• Achyranthes aspera
• Drimia fugax
• Garcinia kola
• Leionema bilobum
• Microtropis japonica
• Morus macroura
• Neopringlea integrifolia
• Raphanus raphanistrum
• Rhizophora mangle
• Salix alba
• Schisandra sphaerandra
• Sesbania grandiflora
• Zinowiewia integerrima

Cross-Links

• PubChem: 14414924
• NPASS: NPC291638
• ChEMBL: CHEMBL364252
• LOTUS: LTS0236412
• wikiData: Q105205049