Showing Compound FMN (FDB030862)

Record Information

Version

1.0

Creation date

2015-05-07 20:19:11 UTC

Update date

2019-11-26 03:21:55 UTC

Primary ID

FDB030862

Secondary Accession Numbers

FDB001984

Chemical Information

FooDB Name

FMN

Description

Flavin mononucleotide, also known as riboflavin 5'-monophosphate or riboflavine dihydrogen phosphate, is a member of the class of compounds known as flavin nucleotides. Flavin nucleotides 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 practically insoluble (in water) and a moderately acidic compound (based on its pKa). Flavin mononucleotide can be found in a number of food items such as spinach, elliott's blueberry, tea leaf willow, and black mulberry, which makes flavin mononucleotide a potential biomarker for the consumption of these food products. Flavin mononucleotide can be found primarily in blood, as well as throughout most human tissues. Flavin mononucleotide exists in all living species, ranging from bacteria to humans. In humans, flavin mononucleotide is involved in several metabolic pathways, some of which include riboflavin metabolism, pyrimidine metabolism, beta-alanine metabolism, and doxorubicin metabolism pathway. Flavin mononucleotide is also involved in several metabolic disorders, some of which include beta ureidopropionase deficiency, UMP synthase deficiency (orotic aciduria), carnosinuria, carnosinemia, and hypophosphatasia. Moreover, flavin mononucleotide is found to be associated with anorexia nervosa. Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, a reversible interconversion of the oxidized (FMN), semiquinone (FMNH•) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization .

CAS Number

146-17-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
5'-monoPhosphate, riboflavin	HMDB
5'-Phosphate, riboflavin	HMDB
Flanin	HMDB
Flavin mononucleotide disodium salt	HMDB
Flavin mononucleotide monosodium salt	HMDB
Flavin mononucleotide monosodium salt, dihydrate	HMDB
Flavin mononucleotide sodium salt	HMDB
Flavine mononucleotide	HMDB
Flavol	HMDB
FMN	HMDB

Showing 1 to 10 of 39 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.67 g/L	ALOGPS
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	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C17H21N4O9P

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

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

Isomeric 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

Average Molecular Weight

456.3438

Monoisotopic Molecular Weight

456.104614802

Classification

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

Physiological effect

Health effect:

Health condition:

Anorexia nervosa

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

Muscle

Cell and elements:

Element:

Platelet

Subcellular:

Biofluid and excreta:

Blood

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Riboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007d-6931400000-cad44822b1dfefb25732	Spectrum
Predicted GC-MS	Riboflavine 5'-(dihydrogen phosphate), 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0592-6901126000-2ec87848003ebe8e438d	Spectrum
Predicted GC-MS	Riboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-9000200000-bc07cc2b3950f70a9db3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0a4i-0000900000-6e5ca4123f461d0e208d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-0a4i-0000900000-f1a0fdd1328522519b91	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, positive	splash10-0a4r-2028900000-899e2dcd3bfb217b5766	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, positive	splash10-052f-7289200000-ebb8d8c94ce8d3a5fb86	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, positive	splash10-0006-9782000000-786258c7a5f6feda99e2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, positive	splash10-00dj-4910000000-e978502607653ec51659	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 66V, positive	splash10-006t-3900000000-cd1a65145bae541f2919	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 78V, positive	splash10-0002-3900000000-9be5fed1e1eb535085f6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, positive	splash10-0fr2-4900000000-d58071130f19cd6bc833	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 107V, positive	splash10-0ktb-7900000000-c3b2300acb88daf0d14f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 124V, positive	splash10-052b-9700000000-e2c1ef96f28d92a23db4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 149V, positive	splash10-0kbb-9300000000-91cbf6b5c1f4e37d016a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-000i-0000900000-b60cf8984dd78397651e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-00kf-0096000000-9690dc0d4d8c890d6900	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-0fka-0960000000-6d860483a67d4bd784ab	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-0002-0019000000-60cf80bbeab6e68f82d5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, positive	splash10-004i-0009000000-eea6861c71c50e5ce846	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0134900000-c3ae39f771e510a09ae6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1090000000-8948e075f379e327a852	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03kc-9251600000-e0759dcc125b6178b7f2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-9120000000-656647e95148b2404066	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4778caa348b1cda5e72c	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

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ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

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Dr. Duke ID

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BIGG ID

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KNApSAcK ID

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HET ID

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Food Biomarker Ontology

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VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

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Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

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Old DFC IDS

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Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

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References

Synthesis Reference

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General Reference

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Content Reference

Showing Compound FMN (FDB030862)

Structure for FDB030862 (FMN)