12-Deuterio-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

Details

• Internal ID: 3e27c696-9301-4240-bc74-4111b2342e4f
• Taxonomy: Alkaloids and derivatives > Camptothecins
• IUPAC Name: 12-deuterio-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• SMILES (Canonical): CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
• SMILES (Isomeric): [2H]C1C2=CC3=CC=CC=C3N=C2C4=CC5=C(COC(=O)C5(CC)O)C(=O)N14
• InChI: InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/i9D
• InChI Key: VSJKWCGYPAHWDS-QOWOAITPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆N₂O₄
• Molecular Weight: 349.40 g/mol
• Exact Mass: 349.11728374 g/mol
• Topological Polar Surface Area (TPSA): 79.70 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9168	91.68%
Caco-2	-	0.8415	84.15%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Lysosomes	0.4965	49.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6791	67.91%
P-glycoprotein inhibitior	-	0.8176	81.76%
P-glycoprotein substrate	-	0.8198	81.98%
CYP3A4 substrate	+	0.6645	66.45%
CYP2C9 substrate	-	0.8162	81.62%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.5756	57.56%
CYP inhibitory promiscuity	-	0.5591	55.91%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4887	48.87%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9842	98.42%
Skin irritation	-	0.8236	82.36%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7728	77.28%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.8823	88.23%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5472	54.72%
Acute Oral Toxicity (c)	II	0.7320	73.20%
Estrogen receptor binding	+	0.9049	90.49%
Androgen receptor binding	+	0.7506	75.06%
Thyroid receptor binding	+	0.6183	61.83%
Glucocorticoid receptor binding	+	0.8660	86.60%
Aromatase binding	+	0.6608	66.08%
PPAR gamma	+	0.7084	70.84%
Honey bee toxicity	-	0.8725	87.25%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7332	73.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	25.1 nM; 251.2 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1781	P11387	DNA topoisomerase I	25 nM	IC50	via Super-PRED
CHEMBL1293278	O75496	Geminin	316.2 nM	Potency	via Super-PRED
CHEMBL4331	P68871	Hemoglobin beta chain	5 nM	Potency	via Super-PRED
CHEMBL1955709	P09651	Heterogeneous nuclear ribonucleoprotein A1	82.7 nM	Kd	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	79.4 nM	Potency	via Super-PRED
CHEMBL1293298	Q01453	Peripheral myelin protein 22	239.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5.6 nM	Potency	via Super-PRED
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	2.1 nM	EC50	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	46.5 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	28.2 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.99%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.81%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.91%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.87%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.15%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.11%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.05%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.91%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.26%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.39%	90.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.87%	85.11%
CHEMBL220	P22303	Acetylcholinesterase	81.44%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.08%	93.99%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.14%	98.00%

Plants that contains it

• Camptotheca acuminata
• Paulownia tomentosa
• Plantago depressa
• Sesamum indicum

Cross-Links

• PubChem: 10712763
• NPASS: NPC139114