2.0
2012-05-31 13:47:23 -0600
2015-09-13 15:15:22 -0600
ECMDB01197
M2MDB000293
FADH2
FADH2 is a reduced form of Flavin adenine dinucleotide (FAD). FAD is a redox cofactor involved in several important reactions in metabolism. It can exist in two different redox states, which it converts between by accepting or donating electrons. The molecule consists of a riboflavin moiety (vitamin B2) bound to the phosphate group of an ADP molecule. The flavin group is bound to ribitol, a sugar alcohol, by a carbon-nitrogen bond, not a glycosidic bond. Thus, riboflavin is not technically a nucleotide; the name flavin adenine dinucleotide is a misnomer. FAD can be reduced to FADH2, whereby it accepts two hydrogen atoms.
1,5-Dihydro-FAD
1,5-Dihydro-P-5-ester with adenosine
1,5-dihydro-Riboflavin 5'-(trihydrogen diphosphate) P'->5'-ester with adenosine
1,5-dihydro-Riboflavin 5'-(trihydrogen diphosphoric acid) p'->5'-ester with adenosine
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine (8CI)
Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine (8ci)
Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate}
Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphoric acid}
Adenosine 5-(trihydrogen pyrophosphate)
Adenosine 5-(trihydrogen pyrophosphoric acid)
Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine (7CI)
Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphoric acid 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphoric acid 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine (7ci)
Adenosine pyrophosphoric acid, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Adenosine pyrophosphoric acid, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine
Benzo[gr]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv
benzo[GR]Pteridine riboflavin 5'-(trihydrogen diphosphoric acid) deriv
Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv
Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv.
benzo[g]Pteridine riboflavin 5'-(trihydrogen diphosphoric acid) deriv
benzo[g]Pteridine riboflavin 5'-(trihydrogen diphosphoric acid) deriv.
Dihydro-FAD
Dihydroflavine-adenine dinucleotide
FAD
FADH
FADH2
FDA
Flavin adenine dinucleotide (reduced)
Flavin adenine dinucleotide reduced
Reduced flavine adenine dinucleotide
Riboflavin 5'-(trihydrogen diphosphate), 1,5-dihydro-, P'-5'-ester with adenosine
Riboflavin 5'-(trihydrogen diphosphate), 1,5-dihydro-, P'-5'-ester with adenosine (9CI)
Riboflavin 5'-(trihydrogen diphosphoric acid), 1,5-dihydro-, p'-5'-ester with adenosine
Riboflavin 5'-(trihydrogen diphosphoric acid), 1,5-dihydro-, p'-5'-ester with adenosine (9ci)
C27H35N9O15P2
787.5656
787.172784519
{[(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-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
fadh(.)
1910-41-4
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=C(N2)C(=O)NC(=O)N1
InChI=1S/C27H35N9O15P2/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/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
YPZRHBJKEMOYQH-UYBVJOGSSA-N
Cytosol
logp
-0.23
logs
-2.37
solubility
3.39e+00 g/l
logp
-4.8
pka_strongest_acidic
1.85
pka_strongest_basic
4.01
iupac
{[(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-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
average_mass
787.5656
mono_mass
787.172784519
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=C(N2)C(=O)NC(=O)N1
formula
C27H35N9O15P2
inchi
InChI=1S/C27H35N9O15P2/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/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
inchikey
YPZRHBJKEMOYQH-UYBVJOGSSA-N
polar_surface_area
355.76
refractivity
188.8
polarizability
69.69
rotatable_bond_count
13
acceptor_count
18
donor_count
11
physiological_charge
-2
formal_charge
0
Riboflavin metabolism
ec00740
Specdb::CMs
65421
Specdb::CMs
786399
Specdb::CMs
786400
Specdb::CMs
786401
Specdb::CMs
786402
Specdb::CMs
786403
Specdb::CMs
786404
Specdb::CMs
786405
Specdb::CMs
786406
Specdb::CMs
786407
Specdb::CMs
786408
Specdb::CMs
786409
Specdb::NmrOneD
1659
Specdb::NmrOneD
146810
Specdb::NmrOneD
146811
Specdb::NmrOneD
146812
Specdb::NmrOneD
146813
Specdb::NmrOneD
146814
Specdb::NmrOneD
146815
Specdb::NmrOneD
146816
Specdb::NmrOneD
146817
Specdb::NmrOneD
146818
Specdb::NmrOneD
146819
Specdb::NmrOneD
146820
Specdb::NmrOneD
146821
Specdb::NmrOneD
146822
Specdb::NmrOneD
146823
Specdb::NmrOneD
146824
Specdb::NmrOneD
146825
Specdb::NmrOneD
146826
Specdb::NmrOneD
146827
Specdb::NmrOneD
146828
Specdb::NmrOneD
146829
Specdb::MsMs
1457
Specdb::MsMs
1458
Specdb::MsMs
1459
Specdb::MsMs
179277
Specdb::MsMs
179278
Specdb::MsMs
179279
Specdb::MsMs
181602
Specdb::MsMs
181603
Specdb::MsMs
181604
Specdb::MsMs
2336158
Specdb::MsMs
2336159
Specdb::MsMs
2336160
Specdb::MsMs
2629481
Specdb::MsMs
2629482
Specdb::MsMs
2629483
Specdb::NmrTwoD
1056
Specdb::NmrTwoD
1600
HMDB01197
393487
C01352
17877
FADH2
FDA
FADH
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.
21097882
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.
22080510
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.
17765195
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.
17379776
Zeller HD, Hille R, Jorns MS: Bacterial sarcosine oxidase: identification of novel substrates and a biradical reaction intermediate. Biochemistry. 1989 Jun 13;28(12):5145-54.
2475174
Ramsey AJ, Alderfer JL, Jorns MS: Energy transduction during catalysis by Escherichia coli DNA photolyase. Biochemistry. 1992 Aug 11;31(31):7134-42.
1643047
Ramsey AJ, Jorns MS: Effect of 5-deazaflavin on energy transduction during catalysis by Escherichia coli DNA photolyase. Biochemistry. 1992 Sep 15;31(36):8437-41.
1390627
Jorns MS: DNA photorepair: chromophore composition and function in two classes of DNA photolyases. Biofactors. 1990 Oct;2(4):207-11.
2282137
Kavakli I Halil; Sancar Aziz Analysis of the role of intraprotein electron transfer in photoreactivation by DNA photolyase in vivo. Biochemistry (2004), 43(48), 15103-10.
Fumarate reductase flavoprotein subunit
P00363
FRDA_ECOLI
frdA
http://ecmdb.ca/proteins/P00363.xml
Succinate dehydrogenase iron-sulfur subunit
P07014
DHSB_ECOLI
sdhB
http://ecmdb.ca/proteins/P07014.xml
Bifunctional protein putA
P09546
PUTA_ECOLI
putA
http://ecmdb.ca/proteins/P09546.xml
Cysteine desulfurase
P0A6B7
ISCS_ECOLI
iscS
http://ecmdb.ca/proteins/P0A6B7.xml
D-amino acid dehydrogenase small subunit
P0A6J5
DADA_ECOLI
dadA
http://ecmdb.ca/proteins/P0A6J5.xml
Fumarate reductase subunit C
P0A8Q0
FRDC_ECOLI
frdC
http://ecmdb.ca/proteins/P0A8Q0.xml
Fumarate reductase subunit D
P0A8Q3
FRDD_ECOLI
frdD
http://ecmdb.ca/proteins/P0A8Q3.xml
Anaerobic glycerol-3-phosphate dehydrogenase subunit C
P0A996
GLPC_ECOLI
glpC
http://ecmdb.ca/proteins/P0A996.xml
Anaerobic glycerol-3-phosphate dehydrogenase subunit A
P0A9C0
GLPA_ECOLI
glpA
http://ecmdb.ca/proteins/P0A9C0.xml
Succinate dehydrogenase flavoprotein subunit
P0AC41
DHSA_ECOLI
sdhA
http://ecmdb.ca/proteins/P0AC41.xml
Succinate dehydrogenase hydrophobic membrane anchor subunit
P0AC44
DHSD_ECOLI
sdhD
http://ecmdb.ca/proteins/P0AC44.xml
Fumarate reductase iron-sulfur subunit
P0AC47
FRDB_ECOLI
frdB
http://ecmdb.ca/proteins/P0AC47.xml
NAD(P)H-flavin reductase
P0AEN1
FRE_ECOLI
fre
http://ecmdb.ca/proteins/P0AEN1.xml
Anaerobic glycerol-3-phosphate dehydrogenase subunit B
P13033
GLPB_ECOLI
glpB
http://ecmdb.ca/proteins/P13033.xml
Aerobic glycerol-3-phosphate dehydrogenase
P13035
GLPD_ECOLI
glpD
http://ecmdb.ca/proteins/P13035.xml
Sulfite reductase [NADPH] hemoprotein beta-component
P17846
CYSI_ECOLI
cysI
http://ecmdb.ca/proteins/P17846.xml
Malate:quinone oxidoreductase
P33940
MQO_ECOLI
mqo
http://ecmdb.ca/proteins/P33940.xml
Sulfite reductase [NADPH] flavoprotein alpha-component
P38038
CYSJ_ECOLI
cysJ
http://ecmdb.ca/proteins/P38038.xml
Ferric iron reductase protein fhuF
P39405
FHUF_ECOLI
fhuF
http://ecmdb.ca/proteins/P39405.xml
Succinate dehydrogenase cytochrome b556 subunit
P69054
DHSC_ECOLI
sdhC
http://ecmdb.ca/proteins/P69054.xml
Cysteine desulfurase_
P77444
SUFS_ECOLI
sufS
http://ecmdb.ca/proteins/P77444.xml
Acyl-coenzyme A dehydrogenase
Q47146
FADE_ECOLI
fadE
http://ecmdb.ca/proteins/Q47146.xml
Probable ATP-dependent transporter sufC
P77499
SUFC_ECOLI
sufC
http://ecmdb.ca/proteins/P77499.xml
FeS cluster assembly protein sufB
P77522
SUFB_ECOLI
sufB
http://ecmdb.ca/proteins/P77522.xml
Protein cyaY
P27838
CYAY_ECOLI
cyaY
http://ecmdb.ca/proteins/P27838.xml
NifU-like protein
P0ACD4
NIFU_ECOLI
nifU
http://ecmdb.ca/proteins/P0ACD4.xml
Cysteine desulfuration protein sufE
P76194
SUFE_ECOLI
sufE
http://ecmdb.ca/proteins/P76194.xml
FeS cluster assembly protein sufD
P77689
SUFD_ECOLI
sufD
http://ecmdb.ca/proteins/P77689.xml
Probable ATP-dependent transporter sufC
P77499
SUFC_ECOLI
sufC
http://ecmdb.ca/proteins/P77499.xml
FADH2 + 2 Hydrogen ion + SufBCD with two bound [2Fe-2S] clusters > FAD + SufBCD with bound [4Fe-4S] cluster
FAD + Hydrogen ion + NADPH > FADH2 + NADP
Adenosine triphosphate + FADH2 + 2 Iron + Water + SufBCD scaffold complex + 2 SufSE with bound sulfur > ADP + FAD +7 Hydrogen ion + Phosphate + SufBCD with bound [2Fe-2S] cluster +2 SufSE sulfur acceptor complex
Adenosine triphosphate + FADH2 + 2 Iron + Water + SufBCD with bound [2Fe-2S] cluster + 2 SufSE with bound sulfur > ADP + FAD +7 Hydrogen ion + Phosphate + SufBCD with two bound [2Fe-2S] clusters +2 SufSE sulfur acceptor complex
FADH2 + 2 Iron + 2 IscS with bound sulfur + IscU scaffold protein > FAD +6 Hydrogen ion +2 IscS sulfur acceptor protein + IscU with bound [2Fe-2S] cluster
FADH2 + 2 Iron + 2 IscS with bound sulfur + IscU with bound [2Fe-2S] cluster > FAD +6 Hydrogen ion +2 IscS sulfur acceptor protein + IscU with two bound [2Fe-2S] clusters
Butyryl-CoA + FAD <> Crotonoyl-CoA + FADH2
FAD + Octanoyl-CoA <> FADH2 + (2E)-Octenoyl-CoA
R03777
FAD + Palmityl-CoA <> FADH2 + (2E)-Hexadecenoyl-CoA
R01279
FAD + Tetradecanoyl-CoA <> FADH2 + (2E)-Tetradecenoyl-CoA
R03990
FAD + Hexanoyl-CoA <> FADH2 + trans-2-Hexenoyl-CoA
R04751
FAD + Stearoyl-CoA <> FADH2 + Trans-Octadec-2-enoyl-CoA
Lauroyl-CoA + FAD <> (2E)-Dodecenoyl-CoA + FADH2
R03857
Decanoyl-CoA (N-C10:0CoA) + FAD <> (2E)-Decenoyl-CoA + FADH2
R04754
FAD + L-Proline > L-D-1-Pyrroline-5-carboxylic acid + FADH2 + Hydrogen ion
D-Alanine + FAD + Water > FADH2 + Ammonium + Pyruvic acid
FADH2 + 2 Hydrogen ion + IscU with two bound [2Fe-2S] clusters > FAD + IscU with bound [4Fe-4S] cluster
FADH2 + 2 Fe3+ > FAD +2 Iron +2 Hydrogen ion
FAD + Hydrogen ion + NADH > FADH2 + NAD
FADH2 + 2 Ferroxamine > FAD +2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion
Succinic acid + FAD <> FADH2 + Fumaric acid
R00408
Glycerol 3-phosphate + FAD <> Dihydroxyacetone phosphate + FADH2
R00848
Butanoyl-CoA + FAD <> FADH2 + Crotonoyl-CoA
R01175
L-Malic acid + FAD <> FADH2 + Oxalacetic acid
R01257
Succinic acid + Ubiquinone-10 + FAD <> Fumaric acid + QH2 + FADH2
PW_R002582
Succinic acid + FAD <> FADH2 + Fumaric acid
FAD + Octanoyl-CoA <> FADH2 + (2E)-Octenoyl-CoA
L-Malic acid + FAD <> FADH2 + Oxalacetic acid
Glycerol 3-phosphate + FAD <> Dihydroxyacetone phosphate + FADH2
Succinic acid + FAD <> FADH2 + Fumaric acid
Succinic acid + FAD <> FADH2 + Fumaric acid
FAD + Octanoyl-CoA <> FADH2 + (2E)-Octenoyl-CoA
L-Malic acid + FAD <> FADH2 + Oxalacetic acid
48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco
Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h
37.7
uM
0.0
37 oC
BW25113
Stationary Phase, glucose limited
150800
0
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.
17379776