Bovine Metabolome Database: Showing metabocard for Flavin Mononucleotide (BMDB0001520)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:07 UTC

Update Date

2020-05-21 16:28:35 UTC

BMDB ID

BMDB0001520

Secondary Accession Numbers

BMDB01520

Metabolite Identification

Common Name

Flavin Mononucleotide

Description

Flavin mononucleotide, also known as riboflavin 5'-phosphate or flanin, 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. Flavin mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Flavin mononucleotide exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Riboflavin 5'-(dihydrogen phosphate)	ChEBI
Riboflavin 5'-monophosphate	ChEBI
Riboflavin 5'-phosphate	ChEBI
Riboflavin monophosphate	ChEBI
Riboflavin-5-phosphate	ChEBI
Riboflavine dihydrogen phosphate	ChEBI
Riboflavin 5'-(dihydrogen phosphoric acid)	Generator
Riboflavin 5'-monophosphoric acid	Generator
Riboflavin 5'-phosphoric acid	Generator
Riboflavin monophosphoric acid	Generator
Riboflavin-5-phosphoric acid	Generator
Riboflavine dihydrogen phosphoric acid	Generator
Flanin	HMDB
Flavine mononucleotide	HMDB
Flavol	HMDB
FMN	HMDB
Riboflavin	HMDB
Riboflavin mononucleotide	HMDB
Riboflavin phosphate	HMDB
Riboflavin-5'-phosphate na	HMDB
Riboflavine 5'-monophosphate	HMDB
Riboflavine 5'-phosphate	HMDB
Riboflavine monophosphate	HMDB
Riboflavine phosphate	HMDB
Riboflavine-5'-phosphate	HMDB
Vitamin b2 phosphate	HMDB
5'-monoPhosphate, riboflavin	HMDB
5'-Phosphate, riboflavin	HMDB
Flavin mononucleotide sodium salt	HMDB
Mononucleotide, riboflavin	HMDB
Flavin mononucleotide monosodium salt	HMDB
Flavin mononucleotide monosodium salt, dihydrate	HMDB
Phosphate, sodium riboflavin	HMDB
Riboflavin 5' phosphate	HMDB
Riboflavin phosphate, sodium	HMDB
Mononucleotide, flavin	HMDB
Riboflavin 5' monophosphate	HMDB
Flavin mononucleotide disodium salt	HMDB
Sodium riboflavin phosphate	HMDB

Chemical Formula

C₁₇H₂₁N₄O₉P

Average Molecular Weight

456.3438

Monoisotopic Molecular Weight

456.104614802

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 Name

riboflavin 5'-phosphate

CAS Registry Number

146-17-8

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

InChI Identifier

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

InChI Key

FVTCRASFADXXNN-SCRDCRAPSA-N

Chemical Taxonomy

Description

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
Diazanaphthalene
Pteridine
Quinoxaline
Monoalkyl phosphate
Pyrimidone
Pyrazine
Organic phosphoric acid derivative
Phosphoric acid ester
Benzenoid
Alkyl phosphate
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Azacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin mononucleotide (CHEBI:17621 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	92 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.78	ALOGPS
logP	-1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-2.6	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007d-6931400000-cad44822b1dfefb25732	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0592-6901126000-2ec87848003ebe8e438d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0a4i-0000900000-6e5ca4123f461d0e208d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-0a4i-0000900000-f1a0fdd1328522519b91	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, positive	splash10-0a4r-2028900000-899e2dcd3bfb217b5766	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, positive	splash10-052f-7289200000-ebb8d8c94ce8d3a5fb86	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, positive	splash10-0006-9782000000-786258c7a5f6feda99e2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, positive	splash10-00dj-4910000000-e978502607653ec51659	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 66V, positive	splash10-006t-3900000000-cd1a65145bae541f2919	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 78V, positive	splash10-0002-3900000000-9be5fed1e1eb535085f6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, positive	splash10-0fr2-4900000000-d58071130f19cd6bc833	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 107V, positive	splash10-0ktb-7900000000-c3b2300acb88daf0d14f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 124V, positive	splash10-052b-9700000000-e2c1ef96f28d92a23db4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 149V, positive	splash10-0kbb-9300000000-91cbf6b5c1f4e37d016a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-000i-0000900000-b60cf8984dd78397651e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-00kf-0096000000-9690dc0d4d8c890d6900	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-0fka-0960000000-6d860483a67d4bd784ab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-0002-0019000000-60cf80bbeab6e68f82d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-004i-0009000000-eea6861c71c50e5ce846	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0134900000-c3ae39f771e510a09ae6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1090000000-8948e075f379e327a852	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03kc-9251600000-e0759dcc125b6178b7f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-9120000000-656647e95148b2404066	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4778caa348b1cda5e72c	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Erythrocyte
Eye Lens
Liver
Placenta
Platelet
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arginine and Proline Metabolism		Not Available
beta-Alanine Metabolism		Not Available
Pantothenate and CoA Biosynthesis		Not Available
Riboflavin Metabolism		Not Available
Vitamin B6 Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Eye Lens	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001520

DrugBank ID

DB03247

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Flavin_mononucleotide

METLIN ID

6295

PubChem Compound

643976

PDB ID

Not Available

ChEBI ID

17621

References

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)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Triokinase/FMN cyclase

General function:: Carbohydrate transport and metabolism
Specific function:: Catalyzes both the phosphorylation of dihydroxyacetone and of glyceraldehyde, and the splitting of ribonucleoside diphosphate-X compounds among which FAD is the best substrate. Represses IFIH1-mediated cellular antiviral response.
Gene Name:: TKFC
Uniprot ID:: Q58DK4
Molecular weight:: 59124.0

Enzyme Details

2. Low molecular weight phosphotyrosine protein phosphatase

General function:: Signal transduction mechanisms
Specific function:: Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates.
Gene Name:: ACP1
Uniprot ID:: P11064
Molecular weight:: 18055.0

Reactions

Flavin Mononucleotide + Water → Riboflavin + Hydrogen phosphate	details

Enzyme Details

3. FAD synthase

General function:: Not Available
Specific function:: Catalyzes the adenylation of flavin mononucleotide (FMN) to form flavin adenine dinucleotide (FAD) coenzyme.
Gene Name:: FLAD1
Uniprot ID:: F6R6Q1
Molecular weight:: 54273.0

Reactions

Adenosine triphosphate + Flavin Mononucleotide → FAD + Pyrophosphate	details

Enzyme Details

4. RFK protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: RFK
Uniprot ID:: Q3SZP4
Molecular weight:: 25377.0

Reactions

Adenosine triphosphate + Riboflavin → ADP + Flavin Mononucleotide	details

Enzyme Details

5. Ectonucleotide pyrophosphatase/phosphodiesterase family member 3

General function:: Not Available
Specific function:: Hydrolase that metabolizes extracellular nucleotides, including ATP, GTP, UTP and CTP (By similarity). Limits mast cell and basophil responses during inflammation and during the chronic phases of allergic responses by eliminating the extracellular ATP that functions as signaling molecule and activates basophils and mast cells and induces the release of inflammatory cytokines. Metabolizes extracellular ATP in the lumen of the small intestine, and thereby prevents ATP-induced apoptosis of intestinal plasmacytoid dendritic cells (By similarity). Has also alkaline phosphodiesterase activity (By similarity).
Gene Name:: ENPP3
Uniprot ID:: P15396
Molecular weight:: 99523.0

Reactions

FAD + Water → Adenosine monophosphate + Flavin Mononucleotide	details

Showing metabocard for Flavin Mononucleotide (BMDB0001520)

Structure for BMDB0001520 (Flavin Mononucleotide)

Enzymes

Reactions

Reactions

Reactions

Reactions