MiMeDB: Showing metabocard for Folinic acid (MMDBc0047933)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:16:33 UTC

Update Date

2022-09-01 02:02:17 UTC

MiMeDB ID

MMDBc0047933

Metabolite Identification

Common Name

Folinic acid

Description

Folinic acid (CAS: 58-05-9), also known as leucovorin, is a medication used to decrease the toxic effects of methotrexate (a chemotherapy agent and immune system suppressant) and pyrimethamine (Wikipedia). Folinic acid is the active metabolite of folic acid. Leucovorin is used principally as its calcium salt as an antidote to folic acid antagonists which block the conversion of folic acid to folinic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃N₇O₇

Average Molecular Weight

473.4393

Monoisotopic Molecular Weight

473.165896125

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

68538-85-2

SMILES

Not Available

InChI Identifier

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13-/m0/s1

InChI Key

VVIAGPKUTFNRDU-STQMWFEESA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bladder
Blood
Feces
Fibroblasts
Pancreas
Testis

Tissue Locations

Bladder
Fibroblasts
Pancreas
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x0000564abf9e4e08>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Firmicutes	389	Human Feces; Pig ; Human ; Cattle	Metabolic reconstruction
	Proteobacteria	175	Human Feces; Human ; Pig	Metabolic reconstruction
	Actinobacteria	124	Human Feces; Human	Metabolic reconstruction
	Verrucomicrobia	1	Human	Metabolic reconstruction
	Bacteroidetes	125	Human Feces; Human	Metabolic reconstruction
	Spirochaetes	1	Human Feces	Metabolic reconstruction
	Thaumarchaeota	1	Human Feces	Metabolic reconstruction
	Fusobacteria	17	Human Feces; Human	Metabolic reconstruction
	Synergistetes	2	Human Feces	Metabolic reconstruction
	Euryarchaeota	2	Human Feces	Metabolic reconstruction
	Candidatus Melainabacteria	1	Human Feces	Metabolic reconstruction
	Tenericutes	1	Human Feces	Metabolic reconstruction
	Planctomycetes	1	Human Feces	Metabolic reconstruction
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						HMDB		details
Human	Detected and Quantified	0.0025	0.0036	Adult (>18 years old)	Both	Normal	HMDB	17272488	details
Human Bladder	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Fibroblasts	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Pancreas	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Testis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. doi: 10.1203/00006450-197503000-00001. [PubMed:235753 ]
Bunni MA, Priest DG: Human red blood cell-mediated metabolism of leucovorin [(R,S)5-formyltetrahydrofolate]. Arch Biochem Biophys. 1991 May 1;286(2):633-7. doi: 10.1016/0003-9861(91)90092-w. [PubMed:1897982 ]
Birmingham BK, Greene DS: Analysis of folinic acid in human serum using high-performance liquid chromatography with amperometric detection. J Pharm Sci. 1983 Nov;72(11):1306-9. doi: 10.1002/jps.2600721118. [PubMed:6606033 ]
Straw JA, Szapary D, Wynn WT: Pharmacokinetics of the diastereoisomers of leucovorin after intravenous and oral administration to normal subjects. Cancer Res. 1984 Jul;44(7):3114-9. [PubMed:6609768 ]
Bentivoglio G, Melica F, Cristoforoni P: Folinic acid in the treatment of human male infertility. Fertil Steril. 1993 Oct;60(4):698-701. doi: 10.1016/s0015-0282(16)56225-6. [PubMed:8405528 ]
Jardine LF, Ingram LC, Bleyer WA: Intrathecal leucovorin after intrathecal methotrexate overdose. J Pediatr Hematol Oncol. 1996 Aug;18(3):302-4. doi: 10.1097/00043426-199608000-00014. [PubMed:8689347 ]
Kajiyama Y, Tsurumaru M, Udagawa H, Tsutsumi K, Kinoshita Y, Akiyama H: Relief of jaundice by 5-fluorouracil and folinic acid in patients with recurrent gastric cancer. Surg Oncol. 1996 Aug;5(4):177-81. doi: 10.1016/s0960-7404(96)80041-7. [PubMed:9067566 ]
Joulia JM, Pinguet F, Ychou M, Duffour J, Astre C, Bressolle F: Plasma and salivary pharmacokinetics of 5-fluorouracil (5-FU) in patients with metastatic colorectal cancer receiving 5-FU bolus plus continuous infusion with high-dose folinic acid. Eur J Cancer. 1999 Feb;35(2):296-301. doi: 10.1016/s0959-8049(98)00318-9. [PubMed:10448274 ]
Zhu WY, Alliegro MA, Melera PW: The rate of folate receptor alpha (FR alpha) synthesis in folate depleted CHL cells is regulated by a translational mechanism sensitive to media folate levels, while stable overexpression of its mRNA is mediated by gene amplification and an increase in transcript half-life. J Cell Biochem. 2001 Mar 26;81(2):205-19. doi: 10.1002/1097-4644(20010501)81:2<205::aid-jcb1036>3.0.co;2-s. [PubMed:11241661 ]
Vimercati A, Greco P, D'Apolito A, Angelici MC, Possenti A, Carbonara S, Selvaggi L: [Risk assessment of vertical transmission of Toxoplasma infections]. Acta Biomed Ateneo Parmense. 2000;71 Suppl 1:537-40. [PubMed:11424802 ]
Garbis SD, Melse-Boonstra A, West CE, van Breemen RB: Determination of folates in human plasma using hydrophilic interaction chromatography-tandem mass spectrometry. Anal Chem. 2001 Nov 15;73(22):5358-64. doi: 10.1021/ac010741y. [PubMed:11816560 ]
Sengelov L, von der Maase H, Lundbeck F, Barlebo H, Colstrup H, Engelholm SA, Krarup T, Madsen EL, Meyhoff HH, Mommsen S, Nielsen OS, Pedersen D, Steven K, Sorensen B: Neoadjuvant chemotherapy with cisplatin and methotrexate in patients with muscle-invasive bladder tumours. Acta Oncol. 2002;41(5):447-56. doi: 10.1080/028418602320405041. [PubMed:12442921 ]
Jansman FG, Coenen JL, De Graaf JC, Tobi H, Sleijfer DT, Brouwers JR: Relationship between pharmacokinetics of 5-FU in plasma and in saliva, and toxicity of 5-fluorouracil/folinic acid. Anticancer Res. 2002 Nov-Dec;22(6B):3449-55. [PubMed:12552938 ]
Ramaekers VT, Hausler M, Opladen T, Heimann G, Blau N: Psychomotor retardation, spastic paraplegia, cerebellar ataxia and dyskinesia associated with low 5-methyltetrahydrofolate in cerebrospinal fluid: a novel neurometabolic condition responding to folinic acid substitution. Neuropediatrics. 2002 Dec;33(6):301-8. doi: 10.1055/s-2002-37082. [PubMed:12571785 ]
Micke O, Bruns F, Schafer U, Kurowski R, Horst E, Willich N: CA 19-9 in the therapy monitoring and follow-up of locally advanced cancer of the exocrine pancreas treated with radiochemotherapy. Anticancer Res. 2003 Mar-Apr;23(2A):835-40. [PubMed:12820309 ]
Polyzos A, Kouraklis G, Giannopoulos A, Bramis J, Delladetsima JK, Sfikakis PP: Irinotecan as salvage chemotherapy for advanced small bowel adenocarcinoma: a series of three patients. J Chemother. 2003 Oct;15(5):503-6. doi: 10.1179/joc.2003.15.5.503. [PubMed:14598944 ]
Karakayali FY, Bayar S, Hazinedaroglu S, Sahin F, Karayalcin K: Does folinic acid have a choleretic effect on humans? Turk J Gastroenterol. 2003 Jun;14(2):102-5. [PubMed:14614635 ]
Pfeiffer CM, Fazili Z, McCoy L, Zhang M, Gunter EW: Determination of folate vitamers in human serum by stable-isotope-dilution tandem mass spectrometry and comparison with radioassay and microbiologic assay. Clin Chem. 2004 Feb;50(2):423-32. doi: 10.1373/clinchem.2003.026955. Epub 2003 Dec 11. [PubMed:14670827 ]
Micke O, Hesselmann S, Bruns F, Horst E, Devries A, Schuller P, Willich N, Schafer U: Results and follow-up of locally advanced cancer of the exocrine pancreas treated with radiochemotherapy. Anticancer Res. 2005 May-Jun;25(3A):1523-30. [PubMed:16033054 ]
Pineda M, Ormazabal A, Lopez-Gallardo E, Nascimento A, Solano A, Herrero MD, Vilaseca MA, Briones P, Ibanez L, Montoya J, Artuch R: Cerebral folate deficiency and leukoencephalopathy caused by a mitochondrial DNA deletion. Ann Neurol. 2006 Feb;59(2):394-8. doi: 10.1002/ana.20746. [PubMed:16365882 ]

Showing metabocard for Folinic acid (MMDBc0047933)

MOL for #<Metabolite:0x0000564abf8985b8>

3D MOL for #<Metabolite:0x0000564abf8985b8>

3D SDF for #<Metabolite:0x0000564abf8985b8>

3D-SDF for #<Metabolite:0x0000564abf8985b8>

PDB for #<Metabolite:0x0000564abf8985b8>

3D PDB for #<Metabolite:0x0000564abf8985b8>

SMILES for #<Metabolite:0x0000564abf8985b8>

INCHI for #<Metabolite:0x0000564abf8985b8>

Structure for #<Metabolite:0x0000564abf8985b8>

3D Structure for #<Metabolite:0x0000564abf8985b8>