4-Hydroxy-1,2,6,15-tetraacetyl-9-benzoylagarofuran

Details

• Internal ID: 622e6b85-58f1-42d2-b2c5-965290e61357
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(1S,2S,4S,5R,6R,7S,9R,12R)-4,5,12-triacetyloxy-6-(acetyloxymethyl)-2-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate
• SMILES (Canonical): CC(=O)OCC12C(CC3C(C1(C(CC(C2OC(=O)C)OC(=O)C)(C)O)OC3(C)C)OC(=O)C)OC(=O)C4=CC=CC=C4
• SMILES (Isomeric): CC(=O)OC[C@]12[C@H](C[C@@H]3[C@H]([C@@]1([C@@](C[C@@H]([C@@H]2OC(=O)C)OC(=O)C)(C)O)OC3(C)C)OC(=O)C)OC(=O)C4=CC=CC=C4
• InChI: InChI=1S/C30H38O12/c1-16(31)37-15-29-23(41-26(35)20-11-9-8-10-12-20)13-21-24(39-18(3)33)30(29,42-27(21,5)6)28(7,36)14-22(38-17(2)32)25(29)40-19(4)34/h8-12,21-25,36H,13-15H2,1-7H3/t21-,22+,23+,24-,25+,28+,29-,30+/m1/s1
• InChI Key: SUKGHCPJNGDNSA-LLKZBMCISA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₂
• Molecular Weight: 590.60 g/mol
• Exact Mass: 590.23632664 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• CHEMBL191573
• (3R,5S,5aR,6R,7S,9S,9aS,10R)-6,7,10-tris(acetyloxy)-5a-[(acetyloxy)methyl]-9-hydroxy-2,2,9-trimethyloctahydro-2H-3,9a-methano-1-benzoxepin-5-yl rel-benzoate
• 2H-3,9a-methano-1-benzoxepin-5,6,7,9,10-pentol, 5a-[(acetyloxy)methyl]octahydro-2,2,9-trimethyl-, 6,7,10-triacetate 5-benzoate, (3R,5S,5aR,6R,7S,9S,9aS,10R)-
• Benzoic acid 4,5,12-triacetoxy-6-acetoxymethyl-2-hydroxy-2,10,10-trimethyl-11-oxa-tricyclo[7.2.1.0^(1,6)]dodec-7-yl ester
• InChI=1/C30H38O12/c1-16(31)37-15-29-23(41-26(35)20-11-9-8-10-12-20)13-21-24(39-18(3)33)30(29,42-27(21,5)6)28(7,36)14-22(38-17(2)32)25(29)40-19(4)34/h8-12,21-25,36H,13-15H2,1-7H3/t21-,22+,23+,24-,25+,28+,29-,30+/m1/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9794	97.94%
Caco-2	-	0.7319	73.19%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7136	71.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8872	88.72%
OATP1B3 inhibitior	+	0.8864	88.64%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7801	78.01%
P-glycoprotein inhibitior	+	0.8511	85.11%
P-glycoprotein substrate	-	0.6315	63.15%
CYP3A4 substrate	+	0.6634	66.34%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.6230	62.30%
CYP2C9 inhibition	-	0.6059	60.59%
CYP2C19 inhibition	-	0.6902	69.02%
CYP2D6 inhibition	-	0.9541	95.41%
CYP1A2 inhibition	-	0.7968	79.68%
CYP2C8 inhibition	+	0.7770	77.70%
CYP inhibitory promiscuity	-	0.8693	86.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6003	60.03%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8818	88.18%
Skin irritation	-	0.6920	69.20%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7670	76.70%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6444	64.44%
skin sensitisation	-	0.8606	86.06%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6178	61.78%
Acute Oral Toxicity (c)	I	0.4341	43.41%
Estrogen receptor binding	+	0.8516	85.16%
Androgen receptor binding	+	0.6949	69.49%
Thyroid receptor binding	+	0.6513	65.13%
Glucocorticoid receptor binding	+	0.6844	68.44%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.7366	73.66%
Honey bee toxicity	-	0.8453	84.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5445	54.45%
Fish aquatic toxicity	+	0.9941	99.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.77%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	97.45%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.10%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.45%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	91.45%	97.79%
CHEMBL2581	P07339	Cathepsin D	89.45%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.12%	94.62%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	86.44%	91.65%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.34%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.91%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.33%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.02%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.77%	95.56%
CHEMBL5028	O14672	ADAM10	83.64%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.27%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.32%	97.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.75%	94.08%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.52%	81.11%

Plants that contains it

• Euonymus nanus
• Plenckia populnea
• Tripterygium wilfordii
• Zinowiewia integerrima

Cross-Links

• PubChem: 636819
• LOTUS: LTS0037504
• wikiData: Q104667663