FLAVIN ADENINE DINUCLEOTIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H33N9O15P2
Molecular Weight	785.5497
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FLAVIN ADENINE DINUCLEOTIDE

Structure Search

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]3O[C@H]([C@H](O)[C@@H]3O)N4C=NC5=C4N=CN=C5N)C6=NC(=O)NC(=O)C6=N2

InChI

InChIKey=VWWQXMAJTJZDQX-UYBVJOGSSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H33N9O15P2
Molecular Weight	785.5497
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://med.toaeiyo.co.jp/products/flavitantab/pdf/shiorien-flvt10.pdf
Curator's Comment: description was created based on several sources, including: http://www.wikidoc.org/index.php/FAD http://www.drugbank.ca/drugs/DB03147

Flavin adenine dinucleotide is a coenzyme form of vitamin B2. Many oxidoreductases, called flavoenzymes or flavoproteins, require FAD as a prosthetic group, which functions in electron transfers. It is usually used for the prevention and treatment of various diseases that are caused by Vitamin B2 deficiency or metabolic disorder including stomatitis, eczema, etc. No adverse reactions were reported.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
oxidative phosphorylation 6 Target ID: GO:0006119 Sources: https://www.khanacademy.org/science/biology/cellular-respiration-and-fermentation/oxidative-phosphorylation/a/oxidative-phosphorylation-etc	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Vitamin B2 deficiency 3 Sources: http://med.toaeiyo.co.jp/products/flavitantab/pdf/shiorien-flvt10.pdf	Palliative	Approved 8583	Flavitan Approved Use It is usually used for the prevention and treatment of various diseases that are caused by Vitamin B2 deficiency Launch Date 1966
Conjunctivitis 17 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00054433 http://med.toaeiyo.co.jp/products/flavitantab/pdf/if-flvt.pdf	Palliative	Approved 8583	Flavitan Approved Use It is an effective in conjunctivitis treatment. Launch Date 1966
Stomatitis 7 Sources: http://med.toaeiyo.co.jp/products/flavitantab/pdf/shiorien-flvt10.pdf	Palliative	Approved 8583	Flavitan Approved Use It is usually used for the prevention and treatment of metabolic disorder including stomatitis. Launch Date 1966

PubMed

Title	Date	PubMed
Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.	2015-06-05	25526675
Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin.	2011-04	21308351
Identification and functional characterization of rat riboflavin transporter 2.	2009-04	19122205
Coordinated and reversible reduction of enzymes involved in terminal oxidative metabolism in skeletal muscle mitochondria from a riboflavin-responsive, multiple acyl-CoA dehydrogenase deficiency patient.	2006-03	16470778
Architecture of succinate dehydrogenase and reactive oxygen species generation.	2003-01-31	12560550
Enzymatic and non-enzymatic reduction of brucine N-oxide by aldehyde oxidase and catalase.	2001-11	11765140
Mammalian augmenter of liver regeneration protein is a sulfhydryl oxidase.	2001-03	11346147
Cloning, heterologous expression, and enzymological characterization of human squalene monooxygenase.	2000-02-15	10666321
Structure of fumarate reductase from Wolinella succinogenes at 2.2 A resolution.	1999-11-25	10586875
Determination of riboflavin and flavocoenzymes in human blood plasma by high-performance liquid chromatography.	1995	8546438
Flavin adenine dinucleotide levels in erythrocytes of very low birthweight infants under vitamin supplementation.	1993	8448258
[Comparison of biochemical criteria for supplying the human body with riboflavin].	1991-09-01	1759408
Nutritional status in anorexia nervosa: clinical chemistry, vitamins, iron and zinc.	1988-11	3074921
Riboflavin metabolism in the hypothyroid newborn.	1988-03	3348160
Quantification of riboflavin, riboflavin 5'-phosphate and flavin adenine dinucleotide in plasma and urine by high-performance liquid chromatography.	1987-12-25	3443641
Riboflavin metabolism in the hypothyroid human adult.	1987-02	3809170
ACP1GUA-1--a low-activity variant of human erythrocyte acid phosphatase: association with increased glutathione reductase activity.	1982-05	7081221
Mechanism of chlorpromazine-induced arrhythmia -- arrhythmia and mitochondrial dysfunction.	1981-07	6167651
Protection of chlorpromazine-induced arrhythmia by flavin-adenine-dinucleotide in canine heart.	1979-09	501931
Flavin adenine dinucleotide concentration in erythrocytes with normal and deficient glucose-6-phosphate dehydrogenase.	1970-09-01	5523465

Patents

Sample Use Guides

In Vivo Use Guide

Oral: Take 5 to 45 mg of flavin adenine dinucleotide per day in 1 to 3 divided doses. Injection: 40 mg one or two times per day

Route of Administration: Other

In Vitro Use Guide

The addition of 1uM of FAD was found to exert a consistent activation effect on Glutathione reductase activity.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:49:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:04 GMT 2025`
Record UNII	ZC44YTI8KK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLAVIN ADENINE DINUCLEOTIDE

Common Name

English

FLAVINE ADENINE DINUCLEOTIDE

Preferred Name

English

ADENINE-RIBOFLAVIN DINUCLEOTIDE

Common Name

English

FLAVIN-ADENINE DINUCLEOTIDE [MI]

Common Name

English

RIBOFLAVINE 5'-(TRIHYDROGEN DIPHOSPHATE) 5'->5'-ESTER WITH ADENOSINE

Common Name

English

FLAVINE ADENOSINE DIPHOSPHATE

Common Name

English

FLAVIN ADENIN DINUCLEOTIDE

Common Name

English

NSC-112207

Code

English

RIBOFLAVIN 5'-ADENOSINE DIPHOSPHATE

Common Name

English

FAD

Brand Name

English

FLAVINE-ADENINE DINUCLEOTIDE

Common Name

English

Flavine adenine dinucleotide [WHO-DD]

Common Name

English

RIBOFLAVIN 5'-(TRIHYDROGEN DIPHOSPHATE), P'->5'-ESTER WITH ADENOSINE

Common Name

English

Classification Tree Code System Code

LOINC

53647-4