RIFAPENTINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC J04AB05
UNII XJM390A33U
EPA CompTox DTXSID8041115

Structure

InChI Key WDZCUPBHRAEYDL-GZAUEHORSA-N
Smiles CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C6CCCC6)CC5)c(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C
InChI
InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C47H64N4O12
Molecular Weight 877.04
AlogP 5.65
Hydrogen Bond Acceptor 15.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 5.0
Polar Surface Area 220.15
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 63.0

Bioactivity

Mechanism of Action Action Reference
Bacterial DNA-directed RNA polymerase inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 9910 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 16300 - - -
Assay Description Organism Bioactivity Reference
Inhibition of Staphylococcus epidermidis RNA polymerase mediated transcription Staphylococcus epidermidis 0.08 ug.mL-1
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 0.39 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 36.15 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 20.76 %
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 0.31 % 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 0.07 % 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 0.31 % 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 0.07 %

Related Entries

Cross References

Resources Reference
ChEBI 45304
ChEMBL CHEMBL1660
DrugBank DB01201
FDA SRS XJM390A33U
KEGG C08059
PDB RPT
PubChem 135403821
SureChEMBL SCHEMBL41590
ZINC ZINC000169621228
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