9-AMINOCAMPTOTHECIN

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Synonyms
Status
Molecule Category UNKNOWN
UNII 5MB77ICE2Q
EPA CompTox DTXSID10873202

Structure

InChI Key FUXVKZWTXQUGMW-FQEVSTJZSA-N
Smiles CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(N)cccc3nc2-1
InChI
InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H17N3O4
Molecular Weight 363.37
AlogP 1.66
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 107.44
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 27.0
Assay Description Organism Bioactivity Reference
Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]thymidine into cellular DNA of human cervical cells (CaSki) Homo sapiens 8.5 nM
Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]thymidine into cellular DNA of human colorectal cells (COLO 205) Homo sapiens 6.6 nM
Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]-thymidine into cellular DNA of human lung carcinoma cells (H928) Homo sapiens 7.9 nM
Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]thymidine into cellular DNA of human colorectal cells (HT-29) Homo sapiens 7.4 nM
Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]thymidine into cellular DNA of human hepatocellular cells (HepG2) Homo sapiens 3.5 nM
Compound was tested in vitro for cytotoxicity against L1210 murine leukemia cells. Mus musculus 12.7 nM
Concentration required to inhibit 50% of cell growth in L1210 murine leukemia cell line after 48 hr continuous treatment Mus musculus 12.7 nM
Inhibitory activity in mice bearing L1210 leukemia Mus musculus 12.0 nM
Inhibition of Topoisomerase I by cleavage complex formation in human HL-60 cells None 110.0 nM
Cytotoxicity against human bone marrow cell by CFU-GM assay Homo sapiens 90.0 nM
Cytotoxicity against mouse bone marrow cell by CFU-GM assay Mus musculus 1.0 nM
PUBCHEM_BIOASSAY: Dose response confirmation of uHTS chemical inhibitors of T-cell specific antigen receptor-induced NF-kB activation in a Jurkat cell line using a luminescence assay. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID435003, AID435012, AID465] None 160.0 nM
PUBCHEM_BIOASSAY: Dose Response selectivity of uHTS chemical inhibitors of T-cell specific antigen receptor-induced NF-kB activation in a 697B cell line using a luminescence assay. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID435003, AID435012, AID465] None 620.0 nM
PUBCHEM_BIOASSAY: Fluorescence Cell-Based Dose Response to Characterize Compounds Cytotoxic to RAS-Dependent BJ-TERT-LT-ST Fibroblast. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID1554, AID1674] None 7.18 nM
PubChem BioAssay. Luminescence-based cell-based high throughput dose response assay for agonists of nuclear receptor subfamily 2, group E, member 3 (NR2E3). (Class of assay: confirmatory) Homo sapiens 895.89 nM
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.25 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 22.5 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.9 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -6.8 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media using NBS plates, by Resazurin F(560/590) Staphylococcus aureus subsp. aureus 34.7 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by Resazurin F(560/590) Acinetobacter baumannii -5.64 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by Resazurin F(560/590) Escherichia coli 12.69 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 80.32 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 1.64 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.6 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.01 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.01 %

Related Entries

Cross References

Resources Reference
ChEBI 80755
ChEMBL CHEMBL274070
DrugBank DB12515
FDA SRS 5MB77ICE2Q
KEGG C16822
PubChem 72402
SureChEMBL SCHEMBL26578
ZINC ZINC000037866089
CONTENTS