P. aeruginosa Metabolome Database: Flavin Mononucleotide (PAMDB000408)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000408

Identification

Name:

Flavin Mononucleotide

Description:

FMN is coenzyme for a number of oxidative enzymes including NADH dehydrogenase. It is the principal form in which riboflavin is found in cells.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Flanin
Flavin mononucleotide
Flavine mononucleotide
Flavol
FMN
Riboflavin
Riboflavin 5'-monophosphate
Riboflavin 5'-monophosphoric acid
Riboflavin 5'-phosphate
Riboflavin 5'-phosphoric acid
Riboflavin Mononucleotide
Riboflavin monophosphate
Riboflavin monophosphoric acid
Riboflavin phosphate
Riboflavin phosphoric acid
Riboflavin-5'-phosphate
Riboflavin-5'-phosphate na
Riboflavin-5'-phosphoric acid
Riboflavin-5'-phosphoric acid na
Riboflavin-5-phosphate
Riboflavin-5-phosphoric acid
Riboflavine 5'-monophosphate
Riboflavine 5'-monophosphoric acid
Riboflavine 5'-phosphate
Riboflavine 5'-phosphoric acid
Riboflavine dihydrogen phosphate
Riboflavine dihydrogen phosphoric acid
Riboflavine monophosphate
Riboflavine monophosphoric acid
Riboflavine phosphate
Riboflavine phosphoric acid
Riboflavine-5'-phosphate
Riboflavine-5'-phosphoric acid
Vitamin B2 phosphate
Vitamin b2 phosphoric acid

Chemical Formula:

C₁₇H₂₁N₄O₉P

Average Molecular Weight:

456.3438

Monoisotopic Molecular Weight:

456.104614802

InChI Key:

FVTCRASFADXXNN-SCRDCRAPSA-N

InChI:

InChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1

CAS number:

146-17-8

IUPAC Name:

{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid

Traditional IUPAC Name:

riboflavin 5'-phosphate

SMILES:

CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Flavin nucleotides

Sub Class

Not Available

Direct Parent

Flavin nucleotides

Alternative Parents

Substituents

Flavin nucleotide
Flavin
Isoalloxazine
Quinoxaline
Pteridine
Monoalkyl phosphate
Pyrimidone
Benzenoid
Alkyl phosphate
Pyrimidine
Pyrazine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Polyol
Lactam
1,2-diol
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin mononucleotide (CHEBI:17621 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

290 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	92 mg/mL [HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.668 mg/mL	ALOGPS
logP	-0.78	ALOGPS
logP	-1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.57	ChemAxon
pKa (Strongest Basic)	0.68	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.14 m³·mol^-1	ChemAxon
Polarizability	42.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

More...

Pathways:

Butirosin and neomycin biosynthesis pae00524
Metabolic pathways pae01100
Oxidative phosphorylation pae00190
Porphyrin and chlorophyll metabolism pae00860
Pyrimidine metabolism pae00240
Riboflavin metabolism pae00740
Sulfur metabolism pae00920

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Ahmed F, Khan MR, Akhtaruzzaman M, Karim R, Marks GC, Banu CP, Nahar B, Williams G: Efficacy of twice-weekly multiple micronutrient supplementation for improving the hemoglobin and micronutrient status of anemic adolescent schoolgirls in Bangladesh. Am J Clin Nutr. 2005 Oct;82(4):829-35. Pubmed: 16210713
Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. Pubmed: 2631092
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. Pubmed: 3142982
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. Pubmed: 3592624
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. Pubmed: 7101408
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24. Pubmed: 14689374
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. Pubmed: 9808225
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. Pubmed: 2369885
Buzina R, Grgic Z, Jusic M, Sapunar J, Milanovic N, Brubacher G: Nutritional status and physical working capacity. Hum Nutr Clin Nutr. 1982;36(6):429-38. Pubmed: 7161138
Cikot RJ, Steegers-Theunissen RP, Thomas CM, de Boo TM, Merkus HM, Steegers EA: Longitudinal vitamin and homocysteine levels in normal pregnancy. Br J Nutr. 2001 Jan;85(1):49-58. Pubmed: 11227033
Edelbroek PM, Linssen AC, Zitman FG, Rooymans HG, de Wolff FA: Analgesic and antidepressive effects of low-dose amitriptyline in relation to its metabolism in patients with chronic pain. Clin Pharmacol Ther. 1986 Feb;39(2):156-62. Pubmed: 3510800
Hardwick CC, Herivel TR, Hernandez SC, Ruane PH, Goodrich RP: Separation, identification and quantification of riboflavin and its photoproducts in blood products using high-performance liquid chromatography with fluorescence detection: a method to support pathogen reduction technology. Photochem Photobiol. 2004 Nov-Dec;80(3):609-15. Pubmed: 15382964
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Lartey A, Manu A, Brown KH, Dewey KG: Predictors of micronutrient status among six- to twelve-month-old breast-fed Ghanaian infants. J Nutr. 2000 Feb;130(2):199-207. Pubmed: 10720170
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. Pubmed: 12354259
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. Pubmed: 11606856
Ortega RM, Quintas ME, Martinez RM, Andres P, Lopez-Sobaler AM, Requejo AM: Riboflavin levels in maternal milk: the influence of vitamin B2 status during the third trimester of pregnancy. J Am Coll Nutr. 1999 Aug;18(4):324-9. Pubmed: 12038475
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. Pubmed: 10566553
Schorah CJ, Wild J, Hartley R, Sheppard S, Smithells RW: The effect of periconceptional supplementation on blood vitamin concentrations in women at recurrence risk for neural tube defect. Br J Nutr. 1983 Mar;49(2):203-11. Pubmed: 6830748
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. Pubmed: 3878498
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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. Pubmed: 14963913

Synthesis Reference:

Ono, Shigeru; Hirano, Hiroko; Sato, Yoshiyuki. Formation of flavin adenine dinucleotide and flavin mononucleotide by lens homogenate. Experimental Eye Research (1982), 34(2), 297-301.

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	17621
HMDB ID	HMDB01520
Pubchem Compound ID	710
Kegg ID	C00061
ChemSpider ID	559060
Wikipedia	FMN
BioCyc ID	FMN
EcoCyc ID	FMN
Ligand Expo	FMN

Flavin Mononucleotide (PAMDB000408)

Structure for Flavin Mononucleotide (PAMDB000408)