P. aeruginosa Metabolome Database: FAD (PAMDB110705)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110705

Identification

Name:

FAD

Description:

A flavin adenine dinucleotide in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

flavin adenine dinucleotide oxidized
flavin adenine dinucleotide
flavitan

Chemical Formula:

C₂₇H₃₀N₉O₁₅P₂

Average Molecular Weight:

782.53

Monoisotopic Molecular Weight:

785.1571344576

InChI Key:

IMGVNJNCCGXBHD-UYBVJOGSSA-K

InChI:

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,(H5,28,29,30,34,42,43,44,45,46,47)/p-3/t14-,15+,16+,19-,20+,21+,26+/m0/s1

CAS number:

146-14-5

IUPAC Name:

adenosine 5'-(3-{D-ribo-5-[7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-2,3,4-trihydroxypentyl} dihydrogen diphosphate)

Traditional IUPAC Name:

flavine-adenine dinucleotide

SMILES:

CC6(=C(C)C=C5(C(N=C1(C(=O)[N-]C(=O)N=C1N(CC(C(O)C(O)COP(OP([O-])(OCC4(C(O)C(O)C(N3(C=NC2(C(N)=NC=NC=23)))O4))=O)([O-])=O)O)5))=C6))

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Nucleosides, nucleotides, and analogues

Sub Class

Flavin nucleotides

Direct Parent

Flavin nucleotides

Alternative Parents

Substituents

Flavin nucleotide
(3'->5')-dinucleotide
(3'->5')-dinucleotide or analogue
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Flavin
Pentose phosphate
Pentose-5-phosphate
Isoalloxazine
Glycosyl compound
N-glycosyl compound
Organic pyrophosphate
Diazanaphthalene
6-aminopurine
Pentose monosaccharide
Monosaccharide phosphate
Pteridine
Quinoxaline
Imidazopyrimidine
Purine
Pyrimidone
Monoalkyl phosphate
Aminopyrimidine
N-substituted imidazole
Pyrimidine
Benzenoid
Pyrazine
Alkyl phosphate
Organic phosphoric acid derivative
Primary aromatic amine
Imidolactam
Phosphoric acid ester
Monosaccharide
Heteroaromatic compound
Imidazole
Oxolane
Vinylogous amide
Azole
Secondary alcohol
Lactam
Polyol
Organoheterocyclic compound
Azacycle
Oxacycle
Alcohol
Primary amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin adenine dinucleotide (CHEBI:16238 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.25 mg/mL	ALOGPS
logP	-0.78	ALOGPS
logP	-5.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	4.99	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	70.62 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

D-gluconate + FAD + Hydrogen ion → 2-keto-D-gluconate + FADH2
isovaleryl-CoA + FAD + Hydrogen ion → 3-methylcrotonyl-CoA + FADH2

Pathways:

Ammonia Recycling pae00910
Arginine and Proline Metabolism pae00330
Aspartate Metabolism pae00250
Beta-Alanine Metabolism pae00410
Betaine Metabolism pae00260
Bile Acid Biosynthesis pae00120
Butyrate Metabolism pae00650
Caffeine Metabolism pae00232
Citric Acid Cycle pae00020
D-Arginine and D-Ornithine Metabolism pae00472
Fatty acid Metabolism pae00071
Folate Metabolism pae00670
Glutamate Metabolism pae00250
Glutathione Metabolism pae00480
Glycerolipid Metabolism pae00561
Glycine and Serine Metabolism pae00260
Histidine Metabolism pae00340
Lysine Degradation pae00310
Methionine Metabolism pae00270
Mitochondrial Electron Transport Chain pae00190
Nicotinate and Nicotinamide Metabolism pae00760
Phenylalanine and Tyrosine Metabolism pae00360
Phospholipid Biosynthesis pae00564
Porphyrin Metabolism pae00860
Propanoate Metabolism pae00640
Purine Metabolism pae00230
Pyrimidine Metabolism pae00240
Pyruvate Metabolism pae00620
Riboflavin Metabolism pae00740
Steroid Biosynthesis pae00100
Tryptophan Metabolism pae00380
Tyrosine Metabolism pae00350
Valine, Leucine and Isoleucine Degradation pae00280
Vitamin B6 Metabolism pae00750

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0001200900-b0740b3d33d50996ccde	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000m-0105900000-3abff26d5bb35f8527b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-0931700000-73f360589a13230eea7a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0908600300-b1eccda8ebae8b9e4cc1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-bdb826f9c3cbc09eff9b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019800000-00ad56b6b6a3bb4516e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-667064ca470a5c341974	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0509700500-8766cb874f927ed5a795	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-3125e04c09a14c62f22a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019700000-78c46ea4b4f562757e56	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-94b845d2c8d082b9484c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-6bac7b7f631dfc074a0c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0920000000-49c9d4fb9b57a59f45a5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-572f0b1bd59f71ab3c5f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-d2ede6a2e7183f1c32a3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-78554afbc26abe26af35	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0930000000-274da0a01c651b791733	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-55939cda9e14fc582757	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-db784762434fac3d351f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Ravi G, Venkatesh YP (2014)Recognition of riboflavin and the capsular polysaccharide of Haemophilus influenzae type b by antibodies generated to the haptenic epitope D-ribitol. Glycoconjugate journal 31, Pubmed: 24643482
Ravi G, Venkatesh YP (2014)Recognition of flavin mononucleotide, Haemophilus influenzae type b and its capsular polysaccharide vaccines by antibodies specific to D-ribitol-5-phosphate. Glycoconjugate journal 31, Pubmed: 25108762

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CAS	146-14-5
ChEBI	4956
ChemSpider	13082029
HMDB	HMDB01248
IAF1260	33521
KEGG	C00016
PubChem	15938970
Wikipedia	Flavin_adenine_dinucleotide

FAD (PAMDB110705)

Structure for FAD (PAMDB110705)