(8beta)-8-(acetyloxy)-9-O-benzoyl-2-O-9-O-dideacetyl-8-deoxo-2-O-[(1,6-dihydro-1-methyl-6-oxo-3-pyridinyl)carbony]levonine

Details

• Internal ID: c022fb8f-e4f3-4608-abfe-ac424b55ee19
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1S,3R,13R,14S,17S,18R,19R,20S,21S,22S,23R,24R,25S)-19,22,24-triacetyloxy-20-(acetyloxymethyl)-21-benzoyloxy-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-18-yl] 1-methyl-6-oxopyridine-3-carboxylate
• 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)C6=CC=CC=C6)COC(=O)C)OC(=O)C)OC(=O)C7=CN(C(=O)C=C7)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([C@@]2(C)O)O[C@]4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C6=CC=CC=C6)COC(=O)C)OC(=O)C)OC(=O)C7=CN(C(=O)C=C7)C)C
• InChI: InChI=1S/C48H52N2O19/c1-23-24(2)41(56)67-38-36(66-43(58)30-17-18-32(55)50(9)20-30)40(65-28(6)54)47(22-61-25(3)51)39(68-42(57)29-14-11-10-12-15-29)35(63-26(4)52)33-37(64-27(5)53)48(47,46(38,8)60)69-45(33,7)21-62-44(59)31-16-13-19-49-34(23)31/h10-20,23-24,33,35-40,60H,21-22H2,1-9H3/t23-,24+,33-,35+,36+,37-,38+,39-,40+,45+,46+,47+,48+/m1/s1
• InChI Key: OIYGAGDGUHYHMX-WFSDONNESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₅₂N₂O₁₉
• Molecular Weight: 960.90 g/mol
• Exact Mass: 960.31642743 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 21
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• (8beta)-8-(acetyloxy)-9-O-benzoyl-2-O-9-O-dideacetyl-8-deoxo-2-O-[(1,6-dihydro-1-methyl-6-oxo-3-pyridinyl)carbony]levonine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5512	55.12%
Caco-2	-	0.8543	85.43%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Lysosomes	0.4826	48.26%
OATP2B1 inhibitior	-	0.5781	57.81%
OATP1B1 inhibitior	+	0.8314	83.14%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9544	95.44%
BSEP inhibitior	+	0.9940	99.40%
P-glycoprotein inhibitior	+	0.8154	81.54%
P-glycoprotein substrate	+	0.7856	78.56%
CYP3A4 substrate	+	0.7256	72.56%
CYP2C9 substrate	+	0.5985	59.85%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.7977	79.77%
CYP2C9 inhibition	-	0.6218	62.18%
CYP2C19 inhibition	-	0.6195	61.95%
CYP2D6 inhibition	-	0.9261	92.61%
CYP1A2 inhibition	-	0.7401	74.01%
CYP2C8 inhibition	+	0.7681	76.81%
CYP inhibitory promiscuity	-	0.5932	59.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4845	48.45%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.8186	81.86%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7539	75.39%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8970	89.70%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7210	72.10%
Acute Oral Toxicity (c)	III	0.5223	52.23%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.7641	76.41%
Thyroid receptor binding	+	0.6912	69.12%
Glucocorticoid receptor binding	+	0.7776	77.76%
Aromatase binding	+	0.6561	65.61%
PPAR gamma	+	0.7820	78.20%
Honey bee toxicity	-	0.7092	70.92%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8743	87.43%

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	98.80%	86.33%
CHEMBL2581	P07339	Cathepsin D	98.43%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.34%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.29%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.28%	97.25%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	94.90%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.90%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.65%	93.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.18%	82.69%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.90%	95.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	90.20%	94.42%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.62%	93.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.55%	94.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.40%	96.00%
CHEMBL3891	P07384	Calpain 1	87.89%	93.04%
CHEMBL4208	P20618	Proteasome component C5	87.48%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.76%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.24%	95.56%
CHEMBL5028	O14672	ADAM10	85.65%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.56%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	85.31%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.32%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.30%	83.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.25%	96.67%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.49%	87.67%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.29%	91.43%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 70697733
• LOTUS: LTS0136350
• wikiData: Q27134333