FOLIC ACID

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Search structure


Trade Names	FOLIC ACID FOLICET FOLVITE
Synonyms	Acidum folicum B03BB01 Bio science Folacin Folate Foldine Folettes Foliamin Folic Acid Folic acid Folicare Folicet Folipac Folsan Folvite Incafolic Lexpec Millafol NSC-3073 Natur flow Preconceive Pteroylglutamic acid Roche Vitamin Bc Vitamin M Vitamin b9 Vitamin bc Vitamin m
Status
Molecule Category	Free-form
ATC	B03BB01 V04CX02
UNII	935E97BOY8
EPA CompTox	DTXSID0022519


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

Structure


InChI Key	OVBPIULPVIDEAO-LBPRGKRZSA-N
Smiles	Nc1nc(=O)c2nc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2[nH]1
InChI	InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H19N7O6
Molecular Weight	441.4
AlogP	-0.04
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	6.0
Number of Rotational Bond	9.0
Polar Surface Area	213.28
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	32.0

Assay Description	Organism	Bioactivity	Reference
Thermodynamic Dissociation Constant for compound-Phe31-dihydrofolate reductase (DHFR) complex at pH 7	Escherichia coli	810.0 nM
Inhibitory activity against growth of L1210 leukemia cells in culture	Mus musculus	33.6 %
Dissociation constant against folic acid receptor (FAR); Value ranges from 0.1-1 nM	Homo sapiens	1.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy	Homo sapiens	33.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	98.4 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	109.71 %
Photocytotoxicity against human KB cells overexpressing folate receptor assessed as cell viability incubated for 24 hrs followed by halogen light illumination measured after 20 mins by MTT assay	Homo sapiens	500.0 nM
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	10.57 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	-0.13 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	12.05 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	13.94 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	30.13 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	1.12 %
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	-7.28 %
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	2.02 %
Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli BLR(DE3) assessed as reduction in NADPH level using L-serine, THF and NADP+ at 6.5 or 26.5 uM incubated for 5 mins by SHMT2-MTHFD coupled reaction based fluorescence assay relative to control	Homo sapiens	53.6 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	20.75 %
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	0.07 %

Related Entries

Cross References

Resources	Reference
ChEBI	27470
ChEMBL	CHEMBL1622
DrugBank	DB00158
DrugCentral	1231
FDA SRS	935E97BOY8
Human Metabolome Database	HMDB0000121
Guide to Pharmacology	4562
KEGG	C00504
PDB	FOL
PharmGKB	PA449692
PubChem	6037
SureChEMBL	SCHEMBL3876
ZINC	ZINC000008577218

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).