CID 477607

Details

• Internal ID: 54a87378-d3d2-423f-be76-d7c91f85a286
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1S,3R,13S,14S,17S,18R,19R,20R,21S,22R,23R,24R)-18,19,21,22,24-pentaacetyloxy-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-20-yl]methyl acetate
• SMILES (Canonical): CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
• SMILES (Isomeric): C[C@H]1[C@@H](C(=O)O[C@H]2[C@@H]([C@@H]([C@]3([C@@H]([C@@H]([C@@H]4[C@H]([C@@]3(C2(C)O)O[C@]4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C38H47NO18/c1-16-17(2)33(46)56-30-28(52-20(5)42)32(55-23(8)45)37(15-49-18(3)40)31(54-22(7)44)27(51-19(4)41)25-29(53-21(6)43)38(37,36(30,10)48)57-35(25,9)14-50-34(47)24-12-11-13-39-26(16)24/h11-13,16-17,25,27-32,48H,14-15H2,1-10H3/t16-,17-,25+,27+,28-,29+,30-,31+,32-,35-,36?,37+,38-/m0/s1
• InChI Key: PBFGAFDJVQAMRS-KCYQGYFWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₇NO₁₈
• Molecular Weight: 805.80 g/mol
• Exact Mass: 805.27931365 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 19
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• 33458-82-1
• [(1S,3R,13S,14S,17S,18R,19R,20R,21S,22R,23R,24R)-18,19,21,22,24-Pentaacetyloxy-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-20-yl]methyl acetate
• 8,11-Epoxy-9,12-ethano-11,15-methano-11H-(1,8)dioxacycloheptadecino(4,3-b)pyridine-5,17-dione, 10,13,14,21,22-pentakis(acetyloxy)-12-((acetyloxy)methyl)-7,8,9,10,12,13,14,15,18,19-decahydro-20-hydroxy-8,18,19,20-tetramethyl-, (8R,9R,10R,11S,12S,13R,14R,15S,18S,19S,20S,21S,22R)-
• 8,11-Epoxy-9,12-ethano-11,15-methano-11H-[1,8]dioxacycloheptadecino[4,3-b]pyridine-5,17-dione, 10,13,14,21,22-pentakis(acetyloxy)-12-[(acetyloxy)methyl]-7,8,9,10,12,13,14,15,18,19-decahydro-20-hydroxy-8,18,19,20-tetramethyl-, (8R,9R,10R,11S,12S,13R,14R,15S,18S,19S,20S,21S,22R)-
• DTXSID601019965
• (pentaacetoxy-hydroxy-tetramethyl-dioxo-[?]yl)methyl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8740	87.40%
Caco-2	-	0.8427	84.27%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5278	52.78%
OATP2B1 inhibitior	-	0.7118	71.18%
OATP1B1 inhibitior	+	0.8552	85.52%
OATP1B3 inhibitior	+	0.9073	90.73%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9600	96.00%
P-glycoprotein inhibitior	+	0.8387	83.87%
P-glycoprotein substrate	+	0.7003	70.03%
CYP3A4 substrate	+	0.7047	70.47%
CYP2C9 substrate	-	0.6071	60.71%
CYP2D6 substrate	-	0.8896	88.96%
CYP3A4 inhibition	-	0.7700	77.00%
CYP2C9 inhibition	-	0.7689	76.89%
CYP2C19 inhibition	-	0.7054	70.54%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.6309	63.09%
CYP2C8 inhibition	+	0.5633	56.33%
CYP inhibitory promiscuity	-	0.6539	65.39%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5110	51.10%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8976	89.76%
Skin irritation	-	0.8136	81.36%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4082	40.82%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8477	84.77%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.8525	85.25%
Acute Oral Toxicity (c)	III	0.4652	46.52%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.7356	73.56%
Thyroid receptor binding	+	0.6323	63.23%
Glucocorticoid receptor binding	+	0.7218	72.18%
Aromatase binding	+	0.6543	65.43%
PPAR gamma	+	0.7541	75.41%
Honey bee toxicity	-	0.7563	75.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.7989	79.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.19%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.97%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.80%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.30%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.37%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	95.09%	91.49%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.89%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.78%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.82%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.45%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.56%	93.10%
CHEMBL2039	P27338	Monoamine oxidase B	87.57%	92.51%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.23%	81.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.93%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.30%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.16%	95.56%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.43%	94.42%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.56%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.33%	96.77%
CHEMBL2996	Q05655	Protein kinase C delta	83.87%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.97%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.07%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.01%	100.00%
CHEMBL5028	O14672	ADAM10	81.65%	97.50%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.69%	96.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.24%	95.89%

Plants that contains it

• Peritassa campestris
• Tripterygium wilfordii

Cross-Links

• PubChem: 477607
• LOTUS: LTS0102210
• wikiData: Q105205142