Showing Compound FAD (FDB022511)

Record Information

Version

1.0

Creation date

2011-09-21 00:15:07 UTC

Update date

2020-09-17 15:38:52 UTC

Primary ID

FDB022511

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

FAD

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. In humans, FAD is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, FAD has been detected, but not quantified in, several different foods, such as other bread, passion fruits, asparagus, kelps, and green bell peppers. This could make FAD a potential biomarker for the consumption of these foods. A FAD in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group.

CAS Number

146-14-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
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
Adenosine 5'-(trihydrogen pyroate), 5'-5'-ester with riboflavine	ChEBI
Adenosine 5'-(trihydrogen pyroic acid), 5'-5'-ester with riboflavine	Generator
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diate]	ChEBI
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diic acid]	Generator
FAD	hmdb
Flamitajin B	hmdb
flavin adenine dinucleotide oxidized	hmdb
Flavin-adenine dinucleotide	hmdb
Flavine adenosine diate	HMDB
Riboflavin 5'-(trihydrogen diate), 5'-5'-ester with adenosine	ChEBI
Riboflavin 5'-(trihydrogen diic acid), 5'-5'-ester with adenosine	Generator
Riboflavin 5'-adenosine diate	ChEBI
Riboflavin 5'-adenosine diic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	4.25 g/L	ALOGPS
logP	-0.78	ALOGPS
logP	-4.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	356.42 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	177.43 m³·mol⁻¹	ChemAxon
Polarizability	70.53 Å³	ChemAxon
Number of Rings	6	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

C27H33N9O15P2

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

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

InChI Key

VWWQXMAJTJZDQX-UYBVJOGSSA-N

Isomeric SMILES

CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](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

Average Molecular Weight

785.5497

Monoisotopic Molecular Weight

785.157134455

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
(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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin adenine dinucleotide (CHEBI:16238 )

Ontology

Physiological effect

Health effect:

Health condition:

Anorexia nervosa

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Liver

Tissue and substructures:

Muscle

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	FAD, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0170-1032960400-cdd3286ebb1dea7c4f54	Spectrum
Predicted GC-MS	FAD, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FAD, TBDMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0001200900-b0740b3d33d50996ccde	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000m-0105900000-3abff26d5bb35f8527b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-0931700000-73f360589a13230eea7a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0908600300-b1eccda8ebae8b9e4cc1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-bdb826f9c3cbc09eff9b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019800000-00ad56b6b6a3bb4516e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-667064ca470a5c341974	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0509700500-8766cb874f927ed5a795	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-3125e04c09a14c62f22a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019700000-78c46ea4b4f562757e56	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-94b845d2c8d082b9484c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-6bac7b7f631dfc074a0c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0920000000-49c9d4fb9b57a59f45a5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-572f0b1bd59f71ab3c5f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-d2ede6a2e7183f1c32a3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-78554afbc26abe26af35	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0930000000-274da0a01c651b791733	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-55939cda9e14fc582757	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-db784762434fac3d351f	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0932110400-f05626487523221c34de	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0930000000-86c3d6490bc3a27e053a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-0980000000-58a46c839e0e520474d7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-8482400900-2c4839849821d2807c57	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-5920100000-b38889aa3d09576e2f3e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7l-3900000000-f7144f6355fab252a516	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, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 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
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

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16238

Phenol-Explorer ID

Not Available

DrugBank ID

DB03147

HMDB ID

HMDB01248

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

33521

KNApSAcK ID

Not Available

HET ID

FAD

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

FAD

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)	DAK	Q3LXA3
Putative uncharacterized protein DKFZp686B0215	DKFZp686B0215	Q5HYI4
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 1	NDUFB1	O75438
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 12	NDUFA12	Q9UI09
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 1	NDUFA1	O15239
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4-like 2	NDUFA4L2	Q9NRX3
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 3	NDUFA3	O95167
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 8	NDUFA8	P51970
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4	NDUFA4	O00483
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 11	NDUFA11	Q86Y39
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 6	NDUFA6	P56556
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 4	NDUFB4	O95168
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 7	NDUFA7	O95182
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 2	NDUFA2	O43678
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 5, mitochondrial	NDUFB5	O43674
NADH dehydrogenase [ubiquinone] 1 subunit C2	NDUFC2	O95298
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 3	NDUFB3	O43676
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 7	NDUFB7	P17568
Acyl carrier protein, mitochondrial	NDUFAB1	O14561
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 5	NDUFA5	Q16718
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 9	NDUFB9	Q9Y6M9
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 13	NDUFA13	Q9P0J0
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 11, mitochondrial	NDUFB11	Q9NX14
NADH dehydrogenase (Ubiquinone) 1 beta subcomplex, 2, 8kDa	NDUFB2	A4D1T5