RIBOFLAVIN

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Search structure


Synonyms	Bisulase C.i. 50900 C.i. food yellow 15 E-101(iii) E-b2 E101 Flavaxin Freeda INS NO. 101(I) Ins no.101(iii) Ins-101(iii) Lacto-flavin Lactoflavin NCI-0033298 NSC-33298 Riboflavin Riboflavin (vit b2) Riboflavin tetrabutyrate Riboflavine Riboflavinum Russupteridine yellow iii Vitamin B 2 Vitamin G Vitamin b-2 Vitamin b2 Vitamin b2 (as riboflavin) Vitamin g Vitamin-b2
Status
Molecule Category	Free-form
ATC	S01XA26
UNII	TLM2976OFR
EPA CompTox	DTXSID8021777


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	AUNGANRZJHBGPY-SCRDCRAPSA-N
Smiles	Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C
InChI	InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C17H20N4O6
Molecular Weight	376.37
AlogP	-1.72
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	5.0
Polar Surface Area	161.56
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	27.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of beta-lactamase at 100 uM	None	5.0 %
Inhibition of chymotrypsin at 250 uM	unidentified	5.0 %
Compound was tested for the inhibition of malate dehydrogenase (MDH) at 100 uM	None	5.0 %
Activity at androgen receptor ligand binding domain assessed as inhibition of SRC2-3 interaction at 50 uM after 2 hrs by fluorescence polarization assay	None	223.0 %
Binding affinity to chicken riboflavin binding protein assessed as dissociation constant at pH 9 in 0.1 M Tris by isothermal titration calorimetric assay	Gallus gallus	34.0 nM
Binding affinity to chicken riboflavin binding protein assessed as dissociation constant at pH 4 in 0.1 M NaAc by isothermal titration calorimetric assay	Gallus gallus	46.0 nM
Binding affinity to chicken riboflavin binding protein assessed as dissociation constant at pH 7.4 in 0.1 M phosphate buffer by isothermal titration calorimetric assay	Gallus gallus	6.6 nM
Competitive inhibition of chicken riboflavin binding protein by surface plasmon resonance assay	Gallus gallus	350.0 nM
Binding affinity to chicken riboflavin binding protein assessed as dissociation constant at pH 7.4 in phosphate buffer by isothermal titration calorimetric assay	Gallus gallus	5.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	75.9 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	72.6 %
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	2.82 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control	Escherichia coli	57.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control	Escherichia coli	78.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	38.64 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.693 %
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	-0.09 %		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	-0.23 %		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	-0.23 %		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	-0.09 %

Cross References

Resources	Reference
ChEBI	17015
ChEMBL	CHEMBL1534
DrugBank	DB00140
DrugCentral	2834
FDA SRS	TLM2976OFR
Human Metabolome Database	HMDB0000244
Guide to Pharmacology	6578
KEGG	C00255
PDB	RBF
PharmGKB	PA451242
PubChem	493570
SureChEMBL	SCHEMBL7706
ZINC	ZINC000002036848

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).