Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:43:02 UTC |
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Update Date | 2020-05-21 16:28:35 UTC |
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BMDB ID | BMDB0001248 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | FAD |
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Description | FAD, also known as adeflavin or flamitajin b, 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. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is a strong basic compound (based on its pKa). FAD exists in all living species, ranging from bacteria to humans. |
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Structure | |
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Synonyms | Value | Source |
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Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine | ChEBI | Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate] | ChEBI | Flavin adenine dinucleotide | ChEBI | FLAVIN-adenine dinucleotide | ChEBI | Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine | ChEBI | Riboflavin 5'-adenosine diphosphate | ChEBI | Adeflavin | Kegg | Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'-5'-ester with riboflavine | Generator | Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphoric acid] | Generator | Riboflavin 5'-(trihydrogen diphosphoric acid), 5'-5'-ester with adenosine | Generator | Riboflavin 5'-adenosine diphosphoric acid | Generator | 1H-Purin-6-amine flavin dinucleotide | HMDB | 1H-Purin-6-amine flavine dinucleotide | HMDB | Adenine-flavin dinucleotide | HMDB | Adenine-flavine dinucleotide | HMDB | Adenine-riboflavin dinuceotide | HMDB | Adenine-riboflavin dinucleotide | HMDB | Adenine-riboflavine dinucleotide | HMDB | Flamitajin b | HMDB | Flanin F | HMDB | Flavin adenine dinucleotide oxidized | HMDB | Flavine adenosine diphosphate | HMDB | Flavine-adenine dinucleotide | HMDB | Flavitan | HMDB | Flaziren | HMDB | Isoalloxazine-adenine dinucleotide | HMDB | Riboflavin-adenine dinucleotide | HMDB | Riboflavine-adenine dinucleotide | HMDB | Dinucleotide, flavin-adenine | HMDB |
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Chemical Formula | C27H33N9O15P2 |
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Average Molecular Weight | 785.5497 |
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Monoisotopic Molecular Weight | 785.157134455 |
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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-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid |
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Traditional Name | flavine-adenine dinucleotide |
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CAS Registry Number | 146-14-5 |
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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=NC(=O)NC(=O)C1=N2 |
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InChI Identifier | InChI=1S/C27H33N9O15P2/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/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1 |
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InChI Key | VWWQXMAJTJZDQX-UYBVJOGSSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Flavin nucleotides |
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Sub Class | Not Available |
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Direct Parent | Flavin nucleotides |
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Alternative Parents | |
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Substituents | - Flavin nucleotide
- (3'->5')-dinucleotide
- (3'->5')-dinucleotide or analogue
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Flavin
- Isoalloxazine
- Pentose-5-phosphate
- Pentose phosphate
- Glycosyl compound
- N-glycosyl compound
- Diazanaphthalene
- Pentose monosaccharide
- Pteridine
- 6-aminopurine
- Quinoxaline
- Organic pyrophosphate
- Monosaccharide phosphate
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Aminopyrimidine
- Pyrimidone
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Imidolactam
- Benzenoid
- Alkyl phosphate
- Phosphoric acid ester
- Pyrimidine
- Pyrazine
- Tetrahydrofuran
- Azole
- Vinylogous amide
- Heteroaromatic compound
- Imidazole
- Secondary alcohol
- Lactam
- Polyol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic oxide
- Organic oxygen compound
- Organopnictogen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary amine
- Alcohol
- Amine
- Organic nitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected but not Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0170-1032960400-cdd3286ebb1dea7c4f54 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0001200900-b0740b3d33d50996ccde | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000m-0105900000-3abff26d5bb35f8527b8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-0931700000-73f360589a13230eea7a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000j-0908600300-b1eccda8ebae8b9e4cc1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-bdb826f9c3cbc09eff9b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0019800000-00ad56b6b6a3bb4516e6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000b-0009400000-667064ca470a5c341974 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000j-0509700500-8766cb874f927ed5a795 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-3125e04c09a14c62f22a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0019700000-78c46ea4b4f562757e56 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000b-0009400000-94b845d2c8d082b9484c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0000100900-6bac7b7f631dfc074a0c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0920000000-49c9d4fb9b57a59f45a5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-000i-0003900000-572f0b1bd59f71ab3c5f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-000i-0003900000-d2ede6a2e7183f1c32a3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0000100900-78554afbc26abe26af35 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0930000000-274da0a01c651b791733 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-000i-0003900000-55939cda9e14fc582757 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-000i-0003900000-db784762434fac3d351f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0932110400-f05626487523221c34de | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0930000000-86c3d6490bc3a27e053a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052r-0980000000-58a46c839e0e520474d7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-8482400900-2c4839849821d2807c57 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001l-5920100000-b38889aa3d09576e2f3e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a7l-3900000000-f7144f6355fab252a516 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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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 |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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