(19S)-19-ethyl-19-hydroxy-8-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

Details

• Internal ID: b616e395-46f0-45f6-acd1-4d1c42338566
• Taxonomy: Alkaloids and derivatives > Camptothecins
• IUPAC Name: (19S)-19-ethyl-19-hydroxy-8-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
• SMILES (Canonical): CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5OC)OC6C(C(C(C(O6)CO)O)O)O)N=C4C3=C2)O
• SMILES (Isomeric): CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)N=C4C3=C2)O
• InChI: InChI=1S/C27H28N2O11/c1-3-27(36)14-7-16-19-11(8-29(16)24(34)13(14)10-38-26(27)35)6-12-15(28-19)4-5-17(23(12)37-2)39-25-22(33)21(32)20(31)18(9-30)40-25/h4-7,18,20-22,25,30-33,36H,3,8-10H2,1-2H3/t18-,20-,21+,22-,25-,27+/m1/s1
• InChI Key: IKXVTCBCZXAVDP-JGPVVIQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈N₂O₁₁
• Molecular Weight: 556.50 g/mol
• Exact Mass: 556.16930971 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.73
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6043	60.43%
Caco-2	-	0.8700	87.00%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Lysosomes	0.4981	49.81%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8838	88.38%
P-glycoprotein inhibitior	+	0.6179	61.79%
P-glycoprotein substrate	-	0.6314	63.14%
CYP3A4 substrate	+	0.7101	71.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8672	86.72%
CYP3A4 inhibition	-	0.5711	57.11%
CYP2C9 inhibition	-	0.7967	79.67%
CYP2C19 inhibition	-	0.8367	83.67%
CYP2D6 inhibition	-	0.8804	88.04%
CYP1A2 inhibition	+	0.7013	70.13%
CYP2C8 inhibition	+	0.4553	45.53%
CYP inhibitory promiscuity	-	0.6339	63.39%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5622	56.22%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5517	55.17%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8784	87.84%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5215	52.15%
Acute Oral Toxicity (c)	III	0.4866	48.66%
Estrogen receptor binding	+	0.7992	79.92%
Androgen receptor binding	+	0.7232	72.32%
Thyroid receptor binding	+	0.6020	60.20%
Glucocorticoid receptor binding	+	0.7209	72.09%
Aromatase binding	+	0.6755	67.55%
PPAR gamma	+	0.6556	65.56%
Honey bee toxicity	-	0.8011	80.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4209	42.09%

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	99.71%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.62%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	98.17%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.88%	86.33%
CHEMBL1781	P11387	DNA topoisomerase I	96.15%	97.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.72%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.62%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.52%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.90%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.32%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.93%	97.09%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	88.80%	98.00%
CHEMBL1951	P21397	Monoamine oxidase A	86.20%	91.49%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.33%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.16%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.43%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.14%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.99%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.55%	92.62%
CHEMBL4302	P08183	P-glycoprotein 1	83.34%	92.98%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.84%	95.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.47%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.40%	94.45%

Plants that contains it

• Ophiorrhiza pumila

Cross-Links

• PubChem: 11028089
• LOTUS: LTS0226941
• wikiData: Q105115010