Record Information
Version1.0
Created at2020-04-17 18:50:36 UTC
Updated at2020-12-07 19:11:17 UTC
CannabisDB IDCDB004920
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFlavin mononucleotide
DescriptionFlavin 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. A flavin mononucleotide that is Flavin mononucleotide (vitamin B2) in which the primary hydroxy group has been converted to its dihydrogen phosphate ester. 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. Within humans, flavin mononucleotide participates in a number of enzymatic reactions. In particular, formic acid and flavin mononucleotide can be biosynthesized from FMNH2; which is catalyzed by the enzyme lanosterol 14-alpha demethylase. In addition, formic acid and flavin mononucleotide can be biosynthesized from FMNH2; which is mediated by the enzyme lanosterol 14-alpha demethylase. In humans, flavin mononucleotide is involved in bloch pathway (cholesterol biosynthesis). Outside of the human body, Flavin mononucleotide has been detected, but not quantified in, several different foods, such as lentils, common persimmons, white cabbages, cashew nuts, and lettuces. This could make flavin mononucleotide a potential biomarker for the consumption of these foods. Flavin mononucleotide is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
Riboflavin 5'-(dihydrogen phosphate)ChEBI
Riboflavin 5'-monophosphateChEBI
Riboflavin 5'-phosphateChEBI
Riboflavin monophosphateChEBI
Riboflavin-5-phosphateChEBI
Riboflavine dihydrogen phosphateChEBI
Riboflavin 5'-(dihydrogen phosphoric acid)Generator
Riboflavin 5'-monophosphoric acidGenerator
Riboflavin 5'-phosphoric acidGenerator
Riboflavin monophosphoric acidGenerator
Riboflavin-5-phosphoric acidGenerator
Riboflavine dihydrogen phosphoric acidGenerator
FlaninHMDB
Flavine mononucleotideHMDB
FlavolHMDB
FMNHMDB
RiboflavinHMDB
Riboflavin mononucleotideHMDB
Riboflavin phosphateHMDB
Riboflavin-5'-phosphate naHMDB
Riboflavine 5'-monophosphateHMDB
Riboflavine 5'-phosphateHMDB
Riboflavine monophosphateHMDB
Riboflavine phosphateHMDB
Riboflavine-5'-phosphateHMDB
Vitamin b2 phosphateHMDB
5'-monoPhosphate, riboflavinHMDB
5'-Phosphate, riboflavinHMDB
Flavin mononucleotide sodium saltHMDB
Mononucleotide, riboflavinHMDB
Flavin mononucleotide monosodium saltHMDB
Flavin mononucleotide monosodium salt, dihydrateHMDB
Phosphate, sodium riboflavinHMDB
Riboflavin 5' phosphateHMDB
Riboflavin phosphate, sodiumHMDB
Mononucleotide, flavinHMDB
Riboflavin 5' monophosphateHMDB
Flavin mononucleotide disodium saltHMDB
Sodium riboflavin phosphateHMDB
Chemical FormulaC17H21N4O9P
Average Molecular Weight456.34
Monoisotopic Molecular Weight456.1046
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 Nameriboflavin 5'-phosphate
CAS Registry Number146-17-8
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 KeyFVTCRASFADXXNN-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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassFlavin nucleotides
Sub ClassNot Available
Direct ParentFlavin 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility92 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.78ALOGPS
logP-1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.58 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.14 m³·mol⁻¹ChemAxon
Polarizability42.19 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFlavin mononucleotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007d-6931400000-cad44822b1dfefb25732Spectrum
Predicted GC-MSFlavin mononucleotide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0592-6901126000-2ec87848003ebe8e438dSpectrum
Predicted GC-MSFlavin mononucleotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFlavin mononucleotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000200000-bc07cc2b3950f70a9db32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0a4i-0000900000-6e5ca4123f461d0e208d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0a4i-0000900000-f1a0fdd1328522519b912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-0a4r-2028900000-899e2dcd3bfb217b57662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-052f-7289200000-ebb8d8c94ce8d3a5fb862020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0006-9782000000-786258c7a5f6feda99e22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-00dj-4910000000-e978502607653ec516592020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 66V, positivesplash10-006t-3900000000-cd1a65145bae541f29192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 78V, positivesplash10-0002-3900000000-9be5fed1e1eb535085f62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 91V, positivesplash10-0fr2-4900000000-d58071130f19cd6bc8332020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 107V, positivesplash10-0ktb-7900000000-c3b2300acb88daf0d14f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-052b-9700000000-e2c1ef96f28d92a23db42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 149V, positivesplash10-0kbb-9300000000-91cbf6b5c1f4e37d016a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-000i-0000900000-b60cf8984dd78397651e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-00kf-0096000000-9690dc0d4d8c890d69002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-0fka-0960000000-6d860483a67d4bd784ab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-0002-0019000000-60cf80bbeab6e68f82d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-004i-0009000000-eea6861c71c50e5ce8462020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0134900000-c3ae39f771e510a09ae62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391100000-1b8212d4ae35c1e1f1f22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1090000000-8948e075f379e327a8522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kc-9251600000-e0759dcc125b6178b7f22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9120000000-656647e95148b24040662016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4778caa348b1cda5e72c2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C 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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Lysosomal acid phosphataseACP211p12-p11P11117 details
Low molecular weight phosphotyrosine protein phosphataseACP12p25P24666 details
Tartrate-resistant acid phosphatase type 5ACP519p13.2P13686 details
Prostatic acid phosphataseACPP3q22.1P15309 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Lathosterol oxidaseSC5DL11q23.3O75845 details
NADPH--cytochrome P450 reductasePOR7q11.2P16435 details
Dihydroorotate dehydrogenase (quinone), mitochondrialDHODH16q22Q02127 details
NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialNDUFV111q13P49821 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Methionine synthase reductaseMTRR5p15.31Q9UBK8 details
Pyridoxine-5'-phosphate oxidasePNPO17q21.32Q9NVS9 details
Flavin reductase (NADPH)BLVRB19q13.1-q13.2P30043 details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD1p22Q12882 details
Hydroxyacid oxidase 1HAO120p12Q9UJM8 details
Hydroxyacid oxidase 2HAO21p13.3-p13.1Q9NYQ3 details
Sarcosine dehydrogenase, mitochondrialSARDH9q33-q34Q9UL12 details
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
Riboflavin kinaseRFK9q21.13Q969G6 details
Ribosomal protein S6 kinase alpha-4RPS6KA411q11-q13O75676 details
Serine/threonine-protein kinase Sgk1SGK16q23O00141 details
Phosphopantothenoylcysteine decarboxylasePPCDC15q24.2Q96CD2 details
Lysophosphatidic acid phosphatase type 6ACP61q21Q9NPH0 details
FAD synthaseFLAD11q21.3Q8NFF5 details
NADPH-dependent diflavin oxidoreductase 1NDOR19q34.3Q9UHB4 details
Iodotyrosine dehalogenase 1IYD6q25.1Q6PHW0 details
Testicular acid phosphataseACPT19q13.4Q9BZG2 details
Putative uncharacterized protein ACP1ACP12p25B5MCC7 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Lathosterol oxidaseSC5DL11q23.3O75845 details
NADPH--cytochrome P450 reductasePOR7q11.2P16435 details
NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialNDUFV111q13P49821 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Methionine synthase reductaseMTRR5p15.31Q9UBK8 details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD1p22Q12882 details
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
Riboflavin kinaseRFK9q21.13Q969G6 details
Ribosomal protein S6 kinase alpha-4RPS6KA411q11-q13O75676 details
NADPH-dependent diflavin oxidoreductase 1NDOR19q34.3Q9UHB4 details
tRNA wybutosine-synthesizing protein 1 homologTYW17q11.21Q9NV66 details
tRNA wybutosine-synthesizing protein 1 homolog BTYW1B7q11.23Q6NUM6 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Concentrations Data
Not Available
HMDB IDHMDB0001520
DrugBank IDDB03247
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030862
KNApSAcK IDC00019686
Chemspider ID559060
KEGG Compound IDC00061
BioCyc IDFMN
BiGG ID33703
Wikipedia LinkFlavin_mononucleotide
METLIN ID6295
PubChem Compound643976
PDB IDNot Available
ChEBI ID17621
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 50 proteins in total.

Enzymes

General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACP2
Uniprot ID:
P11117
Molecular weight:
48343.92
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
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
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
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
POR
Uniprot ID:
P16435
Molecular weight:
77047.575
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:
DHODH
Uniprot ID:
Q02127
Molecular weight:
42866.93
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFV1
Uniprot ID:
P49821
Molecular weight:
49867.66
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54

Transporters

General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3

Only showing the first 10 proteins. There are 50 proteins in total.