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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:22 UTC
HMDB IDHMDB00244
Secondary Accession NumbersNone
Metabolite Identification
Common NameRiboflavin
DescriptionRiboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolizing of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin is found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. Riboflavin is yellow or orange-yellow in color and in addition to being used as a food coloring it is also used to fortify some foods. It can be found in baby foods, breakfast cereals, sauces, processed cheese, fruit drinks and vitamin-enriched milk products. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin adenine dinucleotide.
Structure
Thumb
Synonyms
ValueSource
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitolChEBI
6,7-Dimethyl-9-D-ribitylisoalloxazineChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dioneChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazineChEBI
7,8-Dimethyl-10-ribitylisoalloxazineChEBI
e101ChEBI
LactoflavinChEBI
RiboflavinaChEBI
RIBOFLAVINEChEBI
RiboflavinumChEBI
Vitamin b2ChEBI
Vitamin gChEBI
(-)-RiboflavinHMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitolHMDB
6,7-Dimethyl-9-ribitylisoalloxazineHMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dioneHMDB
BeflavinHMDB
BeflavineHMDB
benzo[g]Pteridine riboflavin deriv.HMDB
e 101HMDB
FlavaxinHMDB
Flavin BBHMDB
FlaxainHMDB
FOOD Yellow 15HMDB
HyreHMDB
LactobeneHMDB
LactoflavineHMDB
RibipcaHMDB
RibocrisinaHMDB
RibodermHMDB
RibosynHMDB
RibotoneHMDB
RibovelHMDB
Russupteridine yellow IIIHMDB
San yellow bHMDB
VitaflavineHMDB
Vitasan b2HMDB
Chemical FormulaC17H20N4O6
Average Molecular Weight376.3639
Monoisotopic Molecular Weight376.138284392
IUPAC Name7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
Traditional Nameriboflavin
CAS Registry Number83-88-5
SMILES
CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1
InChI Identifier
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
InChI KeyInChIKey=AUNGANRZJHBGPY-SCRDCRAPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassAlloxazines and isoalloxazines
Direct ParentFlavins
Alternative Parents
Substituents
  • Flavin
  • Quinoxaline
  • Hydroxypyrimidine
  • Pyrimidone
  • Benzenoid
  • Pyrimidine
  • Pyrazine
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Porphyrin and chlorophyll metabolism
  • Component of Riboflavin metabolism
  • Essential vitamins
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0847 mg/mLNot Available
LogP-1.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.66 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.92ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.97ChemAxon
pKa (Strongest Basic)0.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.05 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.27 m3·mol-1ChemAxon
Polarizability37.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0019000000-86365dedafa031aa7787View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-4390000000-ac1b59ab7cc2209f4241View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dj-4900000000-72d33eb27b9bd6a13d9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004l-0569000000-874b71fdc78d04853bf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Erythrocyte
  • Heart
  • Kidney
  • Liver
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Riboflavin MetabolismSMP00070map00740
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.845 (0.361-1.77) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.015 (0.0054-0.028) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.385 (0.15-0.96) uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.530 (0.265-1.30) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.35 +/- 0.05 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.710 +/- 0.180 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.754 +/- 0.222 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.880 +/- 0.375 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.058 +/- 0.048 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified0.578 +/- 0.157 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.578 +/- 0.157 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified0.18 +/- 0.08 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.24 +/- 0.24 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.04 +/- 0.01 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.015 +/- 0.018 uMAdolescent (13-18 years old)FemaleAnorexia nervosa details
Cerebrospinal Fluid (CSF)Detected and Quantified0.18 +/- 0.02 uMAdult (>18 years old)Not Specified
Alcoholism
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.14 +/- 0.06 uMAdult (>18 years old)Not Specified
Alcoholism
details
UrineDetected and Quantified4.757 +/- 5.779 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. [182198 ]
Anorexia nervosa
  1. Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [10197568 ]
Associated OMIM IDs
DrugBank IDDB00140
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012160
KNApSAcK IDNot Available
Chemspider ID431981
KEGG Compound IDC00255
BioCyc IDRIBOFLAVIN
BiGG ID34409
Wikipedia LinkRiboflavin
NuGOwiki LinkHMDB00244
Metagene LinkHMDB00244
METLIN ID5249
PubChem Compound493570
PDB IDRBF
ChEBI ID17015
References
Synthesis ReferenceTishler, Max; Pfister, Karl, III; Babson, R. D.; Ladenburg, Kurt; Fleming, Ann J. Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Mathew JL, Kabi BC, Rath B: Anti-oxidant vitamins and steroid responsive nephrotic syndrome in Indian children. J Paediatr Child Health. 2002 Oct;38(5):450-37. [12354259 ]
  3. Booth CK, Clark T, Fenn A: Folic acid, riboflavin, thiamine, and vitamin B-6 status of a group of first-time blood donors. Am J Clin Nutr. 1998 Nov;68(5):1075-80. [9808225 ]
  4. Boisvert WA, Mendoza I, Castaneda C, De Portocarrero L, Solomons NW, Gershoff SN, Russell RM: Riboflavin requirement of healthy elderly humans and its relationship to macronutrient composition of the diet. J Nutr. 1993 May;123(5):915-25. [8487103 ]
  5. Mikalunas V, Fitzgerald K, Rubin H, McCarthy R, Craig RM: Abnormal vitamin levels in patients receiving home total parenteral nutrition. J Clin Gastroenterol. 2001 Nov-Dec;33(5):393-6. [11606856 ]
  6. Belko AZ, Obarzanek E, Roach R, Rotter M, Urban G, Weinberg S, Roe DA: Effects of aerobic exercise and weight loss on riboflavin requirements of moderately obese, marginally deficient young women. Am J Clin Nutr. 1984 Sep;40(3):553-61. [6475825 ]
  7. Alexander M, Emanuel G, Golin T, Pinto JT, Rivlin RS: Relation of riboflavin nutriture in healthy elderly to intake of calcium and vitamin supplements: evidence against riboflavin supplementation. Am J Clin Nutr. 1984 Apr;39(4):540-6. [6546833 ]
  8. Baeckert PA, Greene HL, Fritz I, Oelberg DG, Adcock EW: Vitamin concentrations in very low birth weight infants given vitamins intravenously in a lipid emulsion: measurement of vitamins A, D, and E and riboflavin. J Pediatr. 1988 Dec;113(6):1057-65. [3142982 ]
  9. Maiani G, Mobarhan S, Nicastro A, Virgili F, Scaccini C, Ferro-Luzzi A: [Determination of glutathione reductase activity in erythrocytes and whole blood as an indicator of riboflavin nutrition] Acta Vitaminol Enzymol. 1983;5(3):171-8. [6650303 ]
  10. Bamji MS, Bhaskaram P, Jacob CM: Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles. Ann Nutr Metab. 1987;31(3):191-6. [3592624 ]
  11. Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. [2631092 ]
  12. Kodentsova VM, Vrzhesinskaya OA, Spirichev VB: Fluorometric riboflavin titration in plasma by riboflavin-binding apoprotein as a method for vitamin B2 status assessment. Ann Nutr Metab. 1995;39(6):355-60. [8678471 ]
  13. Bates CJ, Powers HJ: A simple fluorimetric assay for pyridoxamine phosphate oxidase in erythrocyte haemolysates: effects of riboflavin supplementation and of glucose 6-phosphate dehydrogenase deficiency. Hum Nutr Clin Nutr. 1985 Mar;39(2):107-15. [4019261 ]
  14. Brun TA, Chen J, Campbell TC, Boreham J, Feng Z, Parpia B, Shen TF, Li M: Urinary riboflavin excretion after a load test in rural China as a measure of possible riboflavin deficiency. Eur J Clin Nutr. 1990 Mar;44(3):195-206. [2369885 ]
  15. Mulherin DM, Thurnham DI, Situnayake RD: Glutathione reductase activity, riboflavin status, and disease activity in rheumatoid arthritis. Ann Rheum Dis. 1996 Nov;55(11):837-40. [8976642 ]
  16. Rao PN, Levine E, Myers MO, Prakash V, Watson J, Stolier A, Kopicko JJ, Kissinger P, Raj SG, Raj MH: Elevation of serum riboflavin carrier protein in breast cancer. Cancer Epidemiol Biomarkers Prev. 1999 Nov;8(11):985-90. [10566553 ]
  17. Zhou X, Huang C, Hong J, Yao S: [Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer] Wei Sheng Yan Jiu. 2003 Nov;32(6):597-8, 601. [14963913 ]
  18. Thurnham DI, Zheng SF, Munoz N, Crespi M, Grassi A, Hambidge KM, Chai TF: Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer. Nutr Cancer. 1985;7(3):131-43. [3878498 ]
  19. Bates CJ, Prentice AM, Paul AA, Prentice A, Sutcliffe BA, Whitehead RG: Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement. Trans R Soc Trop Med Hyg. 1982;76(2):253-8. [7101408 ]
  20. Dror Y, Stern F, Komarnitsky M: Optimal and stable conditions for the determination of erythrocyte glutathione reductase activation coefficient to evaluate riboflavin status. Int J Vitam Nutr Res. 1994;64(4):257-62. [7883462 ]
  21. Switzer BR, Stark AH, Atwood JR, Ritenbaugh C, Travis RG, Wu HM: Development of a urinary riboflavin adherence marker for a wheat bran fiber community intervention trial. Cancer Epidemiol Biomarkers Prev. 1997 Jun;6(6):439-42. [9184778 ]
  22. Zempleni J, Galloway JR, McCormick DB: Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans. Am J Clin Nutr. 1996 Jan;63(1):54-66. [8604671 ]

Enzymes

General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACP2
Uniprot ID:
P11117
Molecular weight:
48343.92
Reactions
Flavin Mononucleotide + Water → Riboflavin + Phosphoric aciddetails
General function:
Involved in acid phosphatase activity
Specific function:
Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates. Isoform 3 does not possess phosphatase activity.
Gene Name:
ACP1
Uniprot ID:
P24666
Molecular weight:
18042.315
Reactions
Flavin Mononucleotide + Water → Riboflavin + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
Reactions
Flavin Mononucleotide + Water → Riboflavin + Phosphoric aciddetails
General function:
Involved in acid phosphatase activity
Specific function:
A non-specific tyrosine phosphatase that dephosphorylates a diverse number of substrates under acidic conditions (pH 4-6) including alkyl, aryl, and acyl orthophosphate monoesters and phosphorylated proteins. Has lipid phosphatase activity and inactivates lysophosphatidic acid in seminal plasma. Isoform 2: the cellular form also has ecto-5'-nucleotidase activity in dorsal root ganglion (DRG) neurons. Generates adenosine from AMP which acts as a pain suppressor. Acts as a tumor suppressor of prostate cancer through dephosphorylation of ERBB2 and deactivation of MAPK-mediated signaling.
Gene Name:
ACPP
Uniprot ID:
P15309
Molecular weight:
44565.715
Reactions
Flavin Mononucleotide + Water → Riboflavin + Phosphoric aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. Strolin Benedetti M, Tipton KF, Whomsley R: Amine oxidases and monooxygenases in the in vivo metabolism of xenobiotic amines in humans: has the involvement of amine oxidases been neglected? Fundam Clin Pharmacol. 2007 Oct;21(5):467-80. [17868200 ]
General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
References
  1. Bates CJ, Fuller NJ: The effect of riboflavin deficiency on methylenetetrahydrofolate reductase (NADPH) (EC 1.5.1.20) and folate metabolism in the rat. Br J Nutr. 1986 Mar;55(2):455-64. [3676170 ]
  2. Macdonald HM, McGuigan FE, Fraser WD, New SA, Ralston SH, Reid DM: Methylenetetrahydrofolate reductase polymorphism interacts with riboflavin intake to influence bone mineral density. Bone. 2004 Oct;35(4):957-64. [15454103 ]
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
General function:
Involved in catalytic activity
Specific function:
Broad specificity oxidoreductase that catalyzes the NADPH-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone). Contributes to heme catabolism and metabolizes linear tetrapyrroles. Can also reduce the complexed Fe(3+) iron to Fe(2+) in the presence of FMN and NADPH. In the liver, converts biliverdin to bilirubin.
Gene Name:
BLVRB
Uniprot ID:
P30043
Molecular weight:
22119.215
Reactions
Riboflavin reduced + NADP → Riboflavin + NADPHdetails
Riboflavin reduced + NADP → Riboflavin + NADPH + Hydrogen Iondetails
References
  1. Russell TR, Demeler B, Tu SC: Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin. Biochemistry. 2004 Feb 17;43(6):1580-90. [14769034 ]
  2. van Pee KH, Patallo EP: Flavin-dependent halogenases involved in secondary metabolism in bacteria. Appl Microbiol Biotechnol. 2006 May;70(6):631-41. Epub 2006 Mar 17. [16544142 ]
General function:
Involved in riboflavin kinase activity
Specific function:
Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin-mononucleotide (FMN).
Gene Name:
RFK
Uniprot ID:
Q969G6
Molecular weight:
17623.08
Reactions
Adenosine triphosphate + Riboflavin → ADP + Flavin Mononucleotidedetails
References
  1. Werner R, Manthey KC, Griffin JB, Zempleni J: HepG2 cells develop signs of riboflavin deficiency within 4 days of culture in riboflavin-deficient medium. J Nutr Biochem. 2005 Oct;16(10):617-24. [16081269 ]
  2. Solovieva IM, Kreneva RA, Errais Lopes L, Perumov DA: The riboflavin kinase encoding gene ribR of Bacillus subtilis is a part of a 10 kb operon, which is negatively regulated by the yrzC gene product. FEMS Microbiol Lett. 2005 Feb 1;243(1):51-8. [15668000 ]
  3. Ishchuk OP, Iatsyshyn VIu, Dmytruk KV, Voronovs'kyi AIa, Fedorovych DV, Sybirnyi AA: [Construction of the flavinogenic yeast Candida famata strains with high riboflavin kinase activity using gene engineering]. Ukr Biokhim Zh. 2006 Sep-Oct;78(5):63-9. [17290783 ]
  4. Sandoval FJ, Roje S: An FMN hydrolase is fused to a riboflavin kinase homolog in plants. J Biol Chem. 2005 Nov 18;280(46):38337-45. Epub 2005 Sep 23. [16183635 ]
  5. Bertollo CM, Oliveira AC, Rocha LT, Costa KA, Nascimento EB Jr, Coelho MM: Characterization of the antinociceptive and anti-inflammatory activities of riboflavin in different experimental models. Eur J Pharmacol. 2006 Oct 10;547(1-3):184-91. Epub 2006 Jul 26. [16962092 ]
  6. Hirano G, Izumi H, Yasuniwa Y, Shimajiri S, Ke-Yong W, Sasagiri Y, Kusaba H, Matsumoto K, Hasegawa T, Akimoto M, Akashi K, Kohno K: Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin. Int J Oncol. 2011 Apr;38(4):893-902. doi: 10.3892/ijo.2011.938. Epub 2011 Feb 9. [21308351 ]
General function:
Involved in receptor activity
Specific function:
Riboflavin transporter. Riboflavin transport is Na(+)-independent but moderately pH-sensitive. Activity is strongly inhibited by riboflavin analogs, such as lumiflavin. Weakly inhibited by flavin adenine dinucleotide (FAD). In case of infection by retroviruses, acts as a cell receptor to retroviral envelopes similar to the porcine endogenous retrovirus (PERV-A).
Gene Name:
SLC52A1
Uniprot ID:
Q9NWF4
Molecular weight:
46316.245
General function:
Involved in acid phosphatase activity
Specific function:
Hydrolyzes lysophosphatidic acid to monoacylglycerol.
Gene Name:
ACP6
Uniprot ID:
Q9NPH0
Molecular weight:
48853.955
Reactions
Flavin Mononucleotide + Water → Riboflavin + Phosphoric aciddetails
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates receptor tyrosine-protein kinase erbB-4 and inhibits the ligand-induced proteolytic cleavage.
Gene Name:
ACPT
Uniprot ID:
Q9BZG2
Molecular weight:
46089.015
Reactions
Flavin Mononucleotide + Water → Riboflavin + Phosphoric aciddetails
General function:
Involved in protein tyrosine phosphatase activity
Specific function:
Not Available
Gene Name:
ACP1
Uniprot ID:
B5MCC7
Molecular weight:
12230.0

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [9880528 ]