Record Information
Version1.0
Created at2020-04-17 19:08:37 UTC
Updated at2020-11-18 16:39:20 UTC
CannabisDB IDCDB005093
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFADH
DescriptionFADH, also known as 1,5-dihydro-fad or FADH2, 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. FADH is a strong basic compound (based on its pKa). FADH exists in all living species, ranging from bacteria to humans. In humans, FADH is involved in lps and citrate signaling and inflammation. Outside of the human body, FADH has been detected, but not quantified in, several different foods, such as thistles, white lupines, grass pea, deerberries, and passion fruits. This could make FADH a potential biomarker for the consumption of these foods. FADH is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
1,5-Dihydro-fadChEBI
DIHYDROFLAVINE-adenine dinucleotideChEBI
Flavin adenine dinucleotide (reduced)ChEBI
1,5-Dihydro-p-5-ester with adenosineHMDB
1,5-Dihydro-riboflavin 5'-(trihydrogen diphosphate) p'->5'-ester with adenosineHMDB
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazineHMDB
Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazineHMDB
Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate}HMDB
Adenosine 5-(trihydrogen pyrophosphate)HMDB
Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazineHMDB
Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazineHMDB
Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazineHMDB
Benzo[GR]pteridine riboflavin 5'-(trihydrogen diphosphate) derivHMDB
Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) derivHMDB
Dihydro-fadHMDB
FADH2HMDB
FDAHMDB
Flavin adenine dinucleotide reducedHMDB
Reduced flavine adenine dinucleotideHMDB
Chemical FormulaC27H35N9O15P2
Average Molecular Weight787.57
Monoisotopic Molecular Weight787.1728
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional Namefadh(.)
CAS Registry Number1910-41-4
SMILES
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1
InChI Identifier
InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
InChI KeyYPZRHBJKEMOYQH-UYBVJOGSSA-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
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Flavin
  • Pentose phosphate
  • Pentose-5-phosphate
  • Alkyldiarylamine
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Pteridine
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Imidolactam
  • Benzenoid
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Vinylogous amide
  • Urea
  • Lactam
  • Secondary alcohol
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Polyol
  • Primary amine
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP-1.336Wikipedia
Predicted Properties
PropertyValueSource
logP-0.23ALOGPS
logP-4.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area355.76 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity188.8 m³·mol⁻¹ChemAxon
Polarizability69.69 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFADH, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g70-0024960400-5de09e4bdf0187b78529Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0001200900-b0740b3d33d50996ccdeSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000m-0105900000-3abff26d5bb35f8527b8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0931700000-73f360589a13230eea7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0932110400-58a2ec43460cf9df1c4dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0930000000-15d7e9b22a8286323cc5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0960000000-64746c5025e9c53c89b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-1675510900-39158f1ef2e33daa689eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-4940100000-64cc07487da7b6c45ba2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-4900000000-4da9166c58a097f7d7efSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Long-chain specific acyl-CoA dehydrogenase, mitochondrialACADL2q34P28330 details
Short-chain specific acyl-CoA dehydrogenase, mitochondrialACADS12q24.31P16219 details
Medium-chain specific acyl-CoA dehydrogenase, mitochondrialACADM1p31P11310 details
Peroxisomal acyl-coenzyme A oxidase 1ACOX117q25.1Q15067 details
Heme oxygenase 2HMOX216p13.3P30519 details
Isovaleryl-CoA dehydrogenase, mitochondrialIVD15q14-q15P26440 details
Peroxisomal acyl-coenzyme A oxidase 3ACOX34p15.3O15254 details
Glycerol-3-phosphate dehydrogenase, mitochondrialGPD22q24.1P43304 details
Heme oxygenase 1HMOX122q13.1P09601 details
Glutaryl-CoA dehydrogenase, mitochondrialGCDH19p13.2Q92947 details
Flavin reductase (NADPH)BLVRB19q13.1-q13.2P30043 details
Short/branched chain specific acyl-CoA dehydrogenase, mitochondrialACADSB10q26.13P45954 details
L-2-hydroxyglutarate dehydrogenase, mitochondrialL2HGDH14q21.3Q9H9P8 details
Very long-chain specific acyl-CoA dehydrogenase, mitochondrialACADVL17p13.1P49748 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Heme oxygenase 2HMOX216p13.3P30519 details
Glycerol-3-phosphate dehydrogenase, mitochondrialGPD22q24.1P43304 details
Heme oxygenase 1HMOX122q13.1P09601 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Heme oxygenase 1HMOX122q13.1P09601 details
Concentrations Data
Not Available
HMDB IDHMDB0001197
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030853
KNApSAcK IDNot Available
Chemspider ID393487
KEGG Compound IDC01352
BioCyc IDFADH2
BiGG ID132077
Wikipedia LinkFlavin adenine dinucleotide
METLIN ID6073
PubChem Compound446013
PDB IDNot Available
ChEBI ID17877
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADL
Uniprot ID:
P28330
Molecular weight:
47655.275
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADS
Uniprot ID:
P16219
Molecular weight:
44296.705
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:
ACADM
Uniprot ID:
P11310
Molecular weight:
46587.98
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:
ACOX1
Uniprot ID:
Q15067
Molecular weight:
70135.205
General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed. Heme oxygenase 2 could be implicated in the production of carbon monoxide in brain where it could act as a neurotransmitter.
Gene Name:
HMOX2
Uniprot ID:
P30519
Molecular weight:
36032.615
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
IVD
Uniprot ID:
P26440
Molecular weight:
43055.325
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Oxidizes the CoA-esters of 2-methyl-branched fatty acids (By similarity).
Gene Name:
ACOX3
Uniprot ID:
O15254
Molecular weight:
69574.075
General function:
Involved in calcium ion binding
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
P43304
Molecular weight:
80851.99
General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed.
Gene Name:
HMOX1
Uniprot ID:
P09601
Molecular weight:
32818.345
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the oxidative decarboxylation of glutaryl-CoA to crotonyl-CoA and CO(2) in the degradative pathway of L-lysine, L-hydroxylysine, and L-tryptophan metabolism. It uses electron transfer flavoprotein as its electron acceptor. Isoform Short is inactive.
Gene Name:
GCDH
Uniprot ID:
Q92947
Molecular weight:
48126.715

Only showing the first 10 proteins. There are 18 proteins in total.