NIACINAMIDE

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Synonyms
Status
Molecule Category Free-form
UNII 25X51I8RD4
EPA CompTox DTXSID2020929

Structure

InChI Key DFPAKSUCGFBDDF-UHFFFAOYSA-N
Smiles NC(=O)c1cccnc1
InChI
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

Physicochemical Descriptors

Property Name Value
Molecular Formula C6H6N2O
Molecular Weight 122.13
AlogP 0.18
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 55.98
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 9.0
Assay Description Organism Bioactivity Reference
Inhibition of Escherichia coli KPR at 11 mM Homo sapiens 0.0 %
Inhibition of human SIRT1 at 50 uM Homo sapiens 10.6 %
Inhibition of N-terminal His6-tagged SIRT1 coding region (156-664) (unknown origin) expressed in Escherichia coli BL21(DE3) using 31.25 uM ac-RHKKac-AMC and 750 uM NAD+ as substrate at 100 uM after 45 mins by fluorometric analysis Homo sapiens 0.55 %
Inhibition of SIRT6 (unknown origin) at 300 uM using (DABCYL)ISGASE(MyK)DIVHSE(EDANS)G substrate in presence of NAD followed by 1 hr incubation with trypsin by FRET assay Homo sapiens 50.0 %
Antiangiogenic activity in HUVEC assessed as inhibition of tube formation on matrigel at 12.5 ug/ml after 24 hrs by Mayer's hematoxylin staining based light microscopy relative to control Homo sapiens 11.27 %
Inhibition of human SIRT1 expressed in Escherichia coli BL21 at 250 uM using H3K9AcWW as substrate preincubated for 15 mins followed by substrate addition measured after 1 hr by HPLC analysis relative to control Homo sapiens 73.0 %
Inhibition of human SIRT3 expressed in Escherichia coli BL21 at 250 uM using H3K9AcWW as substrate preincubated for 15 mins followed by substrate addition measured after 1 hr by HPLC analysis relative to control Homo sapiens 74.0 %
Inhibition of human SIRT5 expressed in Escherichia coli BL21 at 250 uM using H3K9AcWW as substrate preincubated for 15 mins followed by substrate addition measured after 1 hr by HPLC analysis relative to control Homo sapiens 69.0 %
Inhibition of human SIRT6 (1 to 294 residues) expressed in Escherichia coli Rosetta (DE3) at 250 uM using H3K9AcWW as substrate preincubated for 15 mins followed by substrate addition measured after 1 hr by HPLC analysis relative to control Homo sapiens 76.0 %
Inhibition of human N-terminal His6-SUMO-tagged SIRT2 (38 to 356 residues) expressed in Escherichia coli BL21 at 250 uM using H3K9AcWW as substrate preincubated for 15 mins followed by substrate addition measured after 1 hr by HPLC analysis relative to control Homo sapiens 83.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 11.51 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.02 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 11.31 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 14.85 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 28.24 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.62 %
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 -0.49 %
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 3.91 %
Inhibition of human sirutin 2 assessed as inhibition of susbtrate demyristoylation at 20 uM using (Z)-(Myr)-Lys-AMC as substrate relative to control Homo sapiens 8.7 %
Inhibition of human sirtuin 1 at 500 uM relative to control Homo sapiens 100.0 %
Inhibition of human sirtuin 3 at 500 uM relative to control Homo sapiens 100.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.902 %
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 -0.1 % 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 -0.1 %
Inhibition of recombinant human SIRT5 at 50 uM using flour de lys succinyl as substrate in presence of NAD+ by fluorometric assay relative to control Homo sapiens 67.0 %
Inhibition of recombinant human SIRT1 (133 to 747 residues) expressed in Escherichia coli BL21(DE3) at 50 uM using ZMAL as substrate incubated for 4 hrs in presence of NAD+ followed by incubation with trypsin for 20 mins by trypsin-coupled assay based homogenous fluorescence analysis relative to control Homo sapiens 21.0 %
Inhibition of recombinant human SIRT2 (25 to 389 residues) expressed in Escherichia coli BL21(DE3) at 50 uM using ZMAL as substrate incubated for 4 hrs in presence of NAD+ followed by incubation with trypsin for 20 mins by trypsin-coupled assay based homogenous fluorescence analysis relative to control Homo sapiens 65.0 %
Inhibition of recombinant human SIRT3 (101 to 399 residues) expressed in Escherichia coli BL21(DE3) at 50 uM using ZMAL as substrate incubated for 4 hrs in presence of NAD+ followed by incubation with trypsin for 20 mins by trypsin-coupled assay based homogenous fluorescence analysis relative to control Homo sapiens 48.0 %

Cross References

Resources Reference
ChEBI 17154
ChEMBL CHEMBL1140
DrugBank DB02701
DrugCentral 1906
FDA SRS 25X51I8RD4
Human Metabolome Database HMDB0001406
KEGG C00153
PDB NCA
PubChem 936
SureChEMBL SCHEMBL19978192
ZINC ZINC000000005878
CONTENTS