ContaminantDB: 6-Hydroxy flavin adenine dinucleotide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 20:34:52 UTC

Update Date

2026-05-14 17:44:48 UTC

Accession Number

CHEM040368

Identification

Common Name

6-Hydroxy flavin adenine dinucleotide

Class

Small Molecule

Description

Flavin-adenine dinucleotide (FAD) in which the hydrogen at position 6 of the benzo[g]pteridinedione moiety is substituted by a hydroxy group.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-HO-FAD	ChEBI
6-HYDROXY-flavin-adenine dinucleotide	ChEBI
6-Hydroxyflavin-adenine dinucleotide	ChEBI
6-Hydroxyflavine-adenine dinucleotide	ChEBI
6-Hydroxyriboflavin 5'-(trihydrogen diphosphate) 5'->5'-ester with adenosine	ChEBI
6-OH-Fad	ChEBI
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-2,3,4-trihydroxy-5-(6-hydroxy-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentyl dihydrogen diphosphate	ChEBI
Adenosine 5'-(trihydrogen diphosphate) 5'->5'-ester with 6-hydroxyriboflavin	ChEBI
6-Hydroxyriboflavin 5'-(trihydrogen diphosphoric acid) 5'->5'-ester with adenosine	Generator
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-2,3,4-trihydroxy-5-(6-hydroxy-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentyl dihydrogen diphosphoric acid	Generator
Adenosine 5'-(trihydrogen diphosphoric acid) 5'->5'-ester with 6-hydroxyriboflavin	Generator
6-Hydroxy-7,8-dimethyl-10-(ribityl-5'-ADP)-isoalloxazine	HMDB
6-Hydroxy-fad	HMDB

Chemical Formula

C₂₇H₃₃N₉O₁₆P₂

Average Molecular Mass

801.549 g/mol

Monoisotopic Mass

801.152 g/mol

CAS Registry Number

52301-43-6

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4S)-2,3,4-trihydroxy-5-{6-hydroxy-7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}pentyl]oxy})phosphoryl]oxy})phosphinic acid

Traditional Name

6-hydroxy-fad

SMILES

CC1=C(C)C(O)=C2N=C3C(=O)NC(=O)N=C3N(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)N3C=NC4=C(N)N=CN=C34)C2=C1

InChI Identifier

InChI=1S/C27H33N9O16P2/c1-9-3-11-15(18(39)10(9)2)32-17-24(33-27(44)34-25(17)43)35(11)4-12(37)19(40)13(38)5-49-53(45,46)52-54(47,48)50-6-14-20(41)21(42)26(51-14)36-8-31-16-22(28)29-7-30-23(16)36/h3,7-8,12-14,19-21,26,37-42H,4-6H2,1-2H3,(H,45,46)(H,47,48)(H2,28,29,30)(H,34,43,44)/t12-,13+,14+,19-,20+,21+,26+/m0/s1

InChI Key

BJSUUWFQAMLNKU-OKXKTURISA-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.

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
Organic pyrophosphate
6-aminopurine
Diazanaphthalene
Pentose monosaccharide
Pteridine
Quinoxaline
Monosaccharide phosphate
Purine
Imidazopyrimidine
1-hydroxy-4-unsubstituted benzenoid
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:40260 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.66 g/L	ALOGPS
logP	-1	ALOGPS
logP	-5.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	376.65 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	179.41 m³·mol⁻¹	ChemAxon
Polarizability	72.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0932100210-53f37315ec40b23e0ac8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0931000000-3538e3388fe23d11f6db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0970000000-25dd99cf0c0180b56d92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052f-9382310800-7a79689d89b7001f3285	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053u-6940100000-f40e5ef5d200d04f3e27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-3910000000-907e26305901d23d35ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000190-d34a31c9e5de23375bef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uki-0874962580-368434e28e2c047cb143	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0942300000-9d8dd5a3c36f7951d91d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000090-760be2b6f7b4852f4f18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fba-8203110960-65798116bee8b1c6d018	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9423310000-dff8b36d5ccd2e73af04	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB02654

HMDB ID

HMDB0011612

FooDB ID

FDB028318

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

6FA

Wikipedia Link

Not Available

Chemspider ID

16743795

ChEBI ID

40260

PubChem Compound ID

5287546

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Marshall KR, Gong M, Wodke L, Lamb JH, Jones DJ, Farmer PB, Scrutton NS, Munro AW: The human apoptosis-inducing protein AMID is an oxidoreductase with a modified flavin cofactor and DNA binding activity. J Biol Chem. 2005 Sep 2;280(35):30735-40. Epub 2005 Jun 15.

6-Hydroxy flavin adenine dinucleotide (CHEM040368)

Structure for CHEM040368: 6-Hydroxy flavin adenine dinucleotide