[(1R,3S,13R,14R,17S,18R,19S,20S,21R,22R,23S,24S,25S)-19,22,24-triacetyloxy-18,25-dihydroxy-20-(hydroxymethyl)-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-21-yl] 2-acetyloxy-2-methylpropanoate

Details

• Internal ID: 210deb15-007c-4c43-adb7-5c9d36c89840
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1R,3S,13R,14R,17S,18R,19S,20S,21R,22R,23S,24S,25S)-19,22,24-triacetyloxy-18,25-dihydroxy-20-(hydroxymethyl)-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-21-yl] 2-acetyloxy-2-methylpropanoate
• 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(C)(C)OC(=O)C)CO)OC(=O)C)O)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)C(C)(C)OC(=O)C)CO)OC(=O)C)O)C
• InChI: InChI=1S/C38H49NO18/c1-16-17(2)31(46)54-28-25(45)29(53-20(5)43)37(14-40)30(55-33(48)34(7,8)56-21(6)44)26(51-18(3)41)23-27(52-19(4)42)38(37,36(28,10)49)57-35(23,9)15-50-32(47)22-12-11-13-39-24(16)22/h11-13,16-17,23,25-30,40,45,49H,14-15H2,1-10H3/t16-,17-,23+,25+,26-,27+,28+,29-,30+,35-,36+,37+,38-/m1/s1
• InChI Key: VIWDKWVPCGPPLP-WXUTVKLDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₉NO₁₈
• Molecular Weight: 807.80 g/mol
• Exact Mass: 807.29496371 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.21
• H-Bond Acceptor: 19
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5899	58.99%
Caco-2	-	0.8514	85.14%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4929	49.29%
OATP2B1 inhibitior	-	0.7110	71.10%
OATP1B1 inhibitior	+	0.8497	84.97%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9752	97.52%
P-glycoprotein inhibitior	+	0.8057	80.57%
P-glycoprotein substrate	+	0.7718	77.18%
CYP3A4 substrate	+	0.7294	72.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.8384	83.84%
CYP2C9 inhibition	-	0.7626	76.26%
CYP2C19 inhibition	-	0.7329	73.29%
CYP2D6 inhibition	-	0.9235	92.35%
CYP1A2 inhibition	-	0.6930	69.30%
CYP2C8 inhibition	+	0.6880	68.80%
CYP inhibitory promiscuity	-	0.5482	54.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5055	50.55%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.8218	82.18%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6902	69.02%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8458	84.58%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.8532	85.32%
Acute Oral Toxicity (c)	III	0.5801	58.01%
Estrogen receptor binding	+	0.7754	77.54%
Androgen receptor binding	+	0.7494	74.94%
Thyroid receptor binding	+	0.6350	63.50%
Glucocorticoid receptor binding	+	0.7632	76.32%
Aromatase binding	+	0.6659	66.59%
PPAR gamma	+	0.7868	78.68%
Honey bee toxicity	-	0.7329	73.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4011	40.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.35%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.16%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.01%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.25%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.43%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.82%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.83%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.61%	94.00%
CHEMBL2039	P27338	Monoamine oxidase B	90.98%	92.51%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.08%	82.69%
CHEMBL2996	Q05655	Protein kinase C delta	89.08%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.47%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.71%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.24%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.70%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.47%	96.77%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.34%	89.34%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.57%	91.07%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.91%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	82.78%	94.73%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.76%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.10%	97.09%
CHEMBL5028	O14672	ADAM10	81.57%	97.50%
CHEMBL2535	P11166	Glucose transporter	81.49%	98.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.24%	96.67%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.15%	96.39%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.46%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.12%	81.11%

Plants that contains it

• Catha edulis

Cross-Links

• PubChem: 162877436
• LOTUS: LTS0242932
• wikiData: Q105287052