Compound: folinic acid
SMILES: O=c1nc([nH]c2c1N(C=O)C(CN2)CNc3ccc(C(=O)N[C@H](C(=O)O)CCC(=O)O)cc3)N
InChIKey: VVIAGPKUTFNRDU-ABLWVSNPSA-N
Synonyms: folinic acid, leucovorin, 58-05-9, 5-Formyltetrahydrofolic acid, folinate, Folinic acid-SF, 5-formyltetrahydrofolate, Acide folinique, 5-Formyl-5,6,7,8-tetrahydrofolic acid, (2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid, N5-Formyltetrahydrofolic acid, N5-Formyl-5,6,7,8-tetrahydrofolic acid, Q573I9DVLP, 5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid, DTXSID0048216, CHEBI:15640, (5-formyl-5,6,7,8-tetrahydropteroyl)glutamate, N-(5-formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid, L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid, L-Glutamic acid, N-(4-(((2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-, (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid, (2S)-2-[[4-[(2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid, 5-Formyltetrahydropteroylglutamate, Leukovorin, Leukovorum, Acid, Folinic, Folinic Acid SF, Folinate, Calcium, (2S)-2-((4-(((2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)phenyl)formamido)pentanedioic acid, (2S)-2-((4-((2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid, (2S)-2-((4-((2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid, Leucovorin, Calcium, 5 Formyltetrahydrofolate, RefChem:55462, Monosodium Salt Leucovorin, DTXCID8028216, 5 Formyltetrahydropteroylglutamate, (2S)-2-((4-(((6R)-2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid, 200-361-6, Welcovorin, Wellcovorin, Leucal, l-Leucovorin, Leucoverin, C20H23N7O7, MFCD00867488, [3H]folinic acid, Leucovorinum (acid), Leucovorin [USAN], CHEMBL69905, UNII-Q573I9DVLP, 5-Formyl-tetrahydrofolate, Leucovorinum, folinic_acid, 5-Formyltetrahydropteroylglutamic acid, Citrovoeum factor, HSDB 6544, 5-formyl-THF, EINECS 200-361-6, L-(+)-Folinic acid, Spectrum_000859, Folinic acid (Standard), Prestwick0_000738, Prestwick1_000738, Prestwick2_000738, Prestwick3_000738, Spectrum2_000116, Spectrum3_000479, Spectrum4_000031, Spectrum5_000910, LEUCOVORIN [HSDB], LEUCOVORIN [VANDF], FOLINIC ACID [MI], SCHEMBL8349, CHEMBL1679, 5-formyltetrahydro-folic acid, BSPBio_000696, BSPBio_002218, KBioGR_000461, KBioSS_001339, DivK1c_000222, FOLINIC ACID [MART.], SPBio_000132, SPBio_002635, FOLINIC ACID [WHO-DD], BPBio1_000766, GTPL4816, GTPL6690, SCHEMBL4575698, SCHEMBL10068238, KBio1_000222, KBio2_001339, KBio2_003907, KBio2_006475, KBio3_001438, NINDS_000222, DW385, GLXC-21677, BDBM50039121, EBC-27186, HY-17556R, MSK001720, s5790, AKOS015961207, DB00650, IDI1_000222, AC-13429, FF156776, HY-17556, SBI-0051427.P003, SD-204098, D93089, EN300-27068710, BRD-A75919782-238-01-8, BRD-A75919782-238-08-3, BRD-A75919782-399-02-6, BRD-A75919782-399-03-4, Q45435667, (2S)-2-(4-(((5-formyl-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzamido)pentanedioic acid, (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid, (S)-2-{4-[(2-Amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid, 2-{4-[(2-Amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid, Glutamic acid, N-(p-(((2-amino-5-formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl)amino)benzoyl)-, L-, L-Glutamic acid, N-[4-[[(2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-, N-(4-{[(2-Amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid, N-(P-((((6RS)-2-AMINO-5-FORMYL-5,6,7,8-TETRAHYDRO-4-HYDROXY-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-L-GLUTAMATE, N-[4-({[2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid, N-[4-[[(2-Amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6(RS)-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid
Theoretical properties:
molecular_formula: C20H23N7O7
molecular_weight: 473.4 g/mol
exact_mass: 473.16589610 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 9
heavy_atom_count: 34
topological_polar_surface_area: 216 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from water with 3 mol of water of crystallization.
color: Crystals from water with 3 mol of water of crystallization.
melting_point: >260
solubility: Sparingly soluble in water
vapor_pressure: 2.3X10-21 mm Hg at 25 °C at 25 °C /Estimated/
Descriptions:
pubchem: 5-formyltetrahydrofolic acid is a formyltetrahydrofolic acid in which the formyl group is located at position 5. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a conjugate acid of a 5-formyltetrahydrofolate(2-).
chebi: A formyltetrahydrofolic acid in which the formyl group is located at position 5.
chembl: LEUCOVORIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Folinic acid, also known as leucovorin, is a medication used to decrease the toxic effects of methotrexate and pyrimethamine. It is also used in combination with 5-fluorouracil to treat colorectal cancer and pancreatic cancer, and may be used to treat folate deficiency, anemia, and methanol poisoning. It is taken by mouth, injection into a muscle, or injection into a vein.
Side effects may include trouble sleeping, allergic reactions, or fever. Use in pregnancy or breastfeeding is generally regarded as safe. When used for anemia it is recommended that pernicious anemia as a cause be ruled out first. Folinic acid is a form of folic acid that does not require activation by dihydrofolate reductase to be useful to the body.
Folinic acid was first made in 1945. In 2025, the United States Food and Drug Administration approved leucovorin calcium tablets for cerebral folate deficiency, bypassing standard review and drawing expert criticism. It is on the World Health Organization's List of Essential Medicines.