Human Metabolome Database: Showing metabocard for FAD (HMDB0001248)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (166) Show 166 proteins XML

enzymes (166) Show 166 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:58:04 UTC

HMDB ID

HMDB0001248

Secondary Accession Numbers

HMDB01248

Metabolite Identification

Common Name

FAD

Description

Flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic reactions in metabolism. 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 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. It is a flavoprotein in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042000202D          

 53 58  0  0  0  0            999 V2000
10004.5670 9999.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8593 9999.4773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.8593 9998.6520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.1454 9999.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1454 9998.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.5732 9998.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4315 9998.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1454 9997.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7156 9998.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.996910003.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.424710000.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.705310000.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0037 9998.6520    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.705310002.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2940 9998.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4143 9999.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5890 9999.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5819 9998.6398    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8734 9998.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9927 9999.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1685 9999.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1587 9998.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6631 9996.7762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8732 9996.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.135810002.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.421410001.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.421410001.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.135810000.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.565410002.3775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.850910001.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.850910001.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.565410000.7275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.995810002.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.281310001.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.281310001.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.995810000.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.710310001.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.710310001.9649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7739 9998.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3614 9997.4404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1864 9997.4404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4413 9998.2250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2804 9998.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0255 9997.9541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5776 9997.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3845 9997.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6394 9998.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0873 9998.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.7283 9999.3517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3931 9998.6325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3070 9999.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5000 9999.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1075 9998.2199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  1  0  0  0
  3  5  1  0  0  0  0
  3  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 13  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 12  1  0  0  0  0
 26 14  1  0  0  0  0
 30 31  2  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 28 31  1  0  0  0  0
 30 25  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 38  1  0  0  0  0
 37 38  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 33 10  2  0  0  0  0
 37 11  2  0  0  0  0
 32 35  1  0  0  0  0
 29 34  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 39 42  1  0  0  0  0
 42 22  1  6  0  0  0
 41 23  1  1  0  0  0
 40 24  1  1  0  0  0
 47 48  2  0  0  0  0
 48 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 43 49  1  0  0  0  0
 51 52  2  0  0  0  0
 48 52  1  0  0  0  0
 50 51  1  0  0  0  0
 47 50  1  0  0  0  0
 53 50  1  6  0  0  0
 53 40  1  0  0  0  0
 39 53  1  0  0  0  0
M  END


  Mrv1652309042000202D          

 53 58  0  0  0  0            999 V2000
10004.5670 9999.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8593 9999.4773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.8593 9998.6520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.1454 9999.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1454 9998.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.5732 9998.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4315 9998.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1454 9997.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7156 9998.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.996910003.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.424710000.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.705310000.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0037 9998.6520    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.705310002.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2940 9998.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4143 9999.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5890 9999.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5819 9998.6398    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8734 9998.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9927 9999.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1685 9999.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1587 9998.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6631 9996.7762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8732 9996.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.135810002.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.421410001.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.421410001.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.135810000.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.565410002.3775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.850910001.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.850910001.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.565410000.7275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.995810002.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.281310001.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.281310001.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.995810000.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.710310001.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.710310001.9649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7739 9998.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3614 9997.4404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1864 9997.4404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4413 9998.2250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2804 9998.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0255 9997.9541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5776 9997.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3845 9997.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6394 9998.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0873 9998.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.7283 9999.3517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3931 9998.6325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3070 9999.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5000 9999.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1075 9998.2199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  1  0  0  0
  3  5  1  0  0  0  0
  3  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 13  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 12  1  0  0  0  0
 26 14  1  0  0  0  0
 30 31  2  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 28 31  1  0  0  0  0
 30 25  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 38  1  0  0  0  0
 37 38  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 33 10  2  0  0  0  0
 37 11  2  0  0  0  0
 32 35  1  0  0  0  0
 29 34  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 39 42  1  0  0  0  0
 42 22  1  6  0  0  0
 41 23  1  1  0  0  0
 40 24  1  1  0  0  0
 47 48  2  0  0  0  0
 48 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 43 49  1  0  0  0  0
 51 52  2  0  0  0  0
 48 52  1  0  0  0  0
 50 51  1  0  0  0  0
 47 50  1  0  0  0  0
 53 50  1  6  0  0  0
 53 40  1  0  0  0  0
 39 53  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001248

> <DATABASE_NAME>
hmdb

> <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=NC(=O)NC(=O)C1=N2

> <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

> <FORMULA>
C27H33N9O15P2

> <MOLECULAR_WEIGHT>
785.5497

> <EXACT_MASS>
785.157134455

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
70.5310152616057

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_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-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-4.681078144323199

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.1867213383834065

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8536451578834567

> <JCHEM_PKA_STRONGEST_BASIC>
4.005031442352912

> <JCHEM_POLAR_SURFACE_AREA>
356.4199999999999

> <JCHEM_REFRACTIVITY>
177.4308

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flavine-adenine dinucleotide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8675.1928666.482   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8673.8718665.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8673.8718664.150   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.5388666.463   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8672.5388663.382   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8675.2038663.382   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8671.2058664.150   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8672.5388661.841   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8669.8698663.382   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8677.8618672.644   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8680.5268668.022   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8669.8508668.022   0.000  0.00  0.00           C+0
HETATM   13  P   UNK     0    8668.5408664.150   0.000  0.00  0.00           P+0
HETATM   14  C   UNK     0    8669.8508671.103   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8667.2158663.359   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8669.3078665.485   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8667.7668665.485   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0    8665.8868664.128   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0    8664.5648663.336   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8666.6538665.462   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8665.1158665.462   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8663.2308664.104   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8662.3048660.649   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8658.9638660.634   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8672.5208671.105   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8671.1878670.335   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8671.1878668.795   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.5208668.025   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0    8675.1898671.105   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0    8673.8558670.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.8558668.794   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0    8675.1898668.025   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0    8677.8598671.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8676.5258670.334   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8676.5258668.794   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0    8677.8598668.024   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0    8679.1938668.794   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0    8679.1938670.334   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0    8660.6458664.259   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0    8659.8758661.889   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8661.4158661.889   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8661.8908663.353   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0    8654.1238664.312   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0    8653.6488662.848   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0    8654.6788661.703   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0    8656.1848662.023   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0    8656.6608663.488   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0    8655.6308664.632   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0    8653.0938665.457   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0    8658.0678664.114   0.000  0.00  0.00           N+0
HETATM   51  C   UNK     0    8657.9068665.646   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0    8656.4008665.966   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0    8659.4018663.344   0.000  0.00  0.00           C+0
CONECT    1    2   32                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    5    6                                                  
CONECT    4    2                                                            
CONECT    5    3    7    8                                                  
CONECT    6    3                                                            
CONECT    7    5    9                                                       
CONECT    8    5                                                            
CONECT    9    7   13                                                       
CONECT   10   33                                                            
CONECT   11   37                                                            
CONECT   12   27                                                            
CONECT   13    9   15   16   17                                             
CONECT   14   26                                                            
CONECT   15   13   18                                                       
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   15   19   20   21                                             
CONECT   19   18   22                                                       
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   19   42                                                       
CONECT   23   41                                                            
CONECT   24   40                                                            
CONECT   25   26   30                                                       
CONECT   26   25   27   14                                                  
CONECT   27   26   28   12                                                  
CONECT   28   27   31                                                       
CONECT   29   30   34                                                       
CONECT   30   31   29   25                                                  
CONECT   31   30   32   28                                                  
CONECT   32   31    1   35                                                  
CONECT   33   34   38   10                                                  
CONECT   34   33   35   29                                                  
CONECT   35   34   36   32                                                  
CONECT   36   35   37                                                       
CONECT   37   38   36   11                                                  
CONECT   38   33   37                                                       
CONECT   39   42   53                                                       
CONECT   40   41   24   53                                                  
CONECT   41   40   42   23                                                  
CONECT   42   41   39   22                                                  
CONECT   43   48   44   49                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   48   46   50                                                  
CONECT   48   47   43   52                                                  
CONECT   49   43                                                            
CONECT   50   51   47   53                                                  
CONECT   51   52   50                                                       
CONECT   52   51   48                                                       
CONECT   53   50   40   39                                                  
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

Mrv1652309042000202D

53 58  0  0  0  0            999 V2000
10004.5670 9999.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8593 9999.4773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.8593 9998.6520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.1454 9999.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1454 9998.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.5732 9998.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4315 9998.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1454 9997.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7156 9998.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.996910003.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.424710000.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.705310000.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0037 9998.6520    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.705310002.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2940 9998.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4143 9999.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5890 9999.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5819 9998.6398    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8734 9998.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9927 9999.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1685 9999.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1587 9998.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6631 9996.7762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8732 9996.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.135810002.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.421410001.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.421410001.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.135810000.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.565410002.3775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.850910001.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.850910001.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.565410000.7275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.995810002.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.281310001.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.281310001.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.995810000.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.710310001.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.710310001.9649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7739 9998.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3614 9997.4404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1864 9997.4404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4413 9998.2250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2804 9998.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0255 9997.9541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5776 9997.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3845 9997.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6394 9998.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0873 9998.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.7283 9999.3517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3931 9998.6325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3070 9999.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5000 9999.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1075 9998.2199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  1  0  0  0
  3  5  1  0  0  0  0
  3  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 13  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 12  1  0  0  0  0
 26 14  1  0  0  0  0
 30 31  2  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 28 31  1  0  0  0  0
 30 25  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 38  1  0  0  0  0
 37 38  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 33 10  2  0  0  0  0
 37 11  2  0  0  0  0
 32 35  1  0  0  0  0
 29 34  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 39 42  1  0  0  0  0
 42 22  1  6  0  0  0
 41 23  1  1  0  0  0
 40 24  1  1  0  0  0
 47 48  2  0  0  0  0
 48 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 43 49  1  0  0  0  0
 51 52  2  0  0  0  0
 48 52  1  0  0  0  0
 50 51  1  0  0  0  0
 47 50  1  0  0  0  0
 53 50  1  6  0  0  0
 53 40  1  0  0  0  0
 39 53  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001248

> <DATABASE_NAME>
hmdb

> <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=NC(=O)NC(=O)C1=N2

> <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

> <FORMULA>
C27H33N9O15P2

> <MOLECULAR_WEIGHT>
785.5497

> <EXACT_MASS>
785.157134455

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
70.5310152616057

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_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-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-4.681078144323199

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.1867213383834065

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8536451578834567

> <JCHEM_PKA_STRONGEST_BASIC>
4.005031442352912

> <JCHEM_POLAR_SURFACE_AREA>
356.4199999999999

> <JCHEM_REFRACTIVITY>
177.4308

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flavine-adenine dinucleotide

> <JCHEM_VEBER_RULE>
0

$$$$

View in JSmol View Stereo Labels

Synonyms

Value	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

Chemical Formula

C₂₇H₃₃N₉O₁₅P₂

Average Molecular Weight

785.5497

Monoisotopic Molecular Weight

785.157134455

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

Traditional Name

flavine-adenine dinucleotide

CAS Registry Number

146-14-5

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=NC(=O)NC(=O)C1=N2

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

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
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:

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Biochemical process:

Fatty acid metabolism

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

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 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0170-1032960400-cdd3286ebb1dea7c4f54	2017-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0001200900-b0740b3d33d50996ccde	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000m-0105900000-3abff26d5bb35f8527b8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-0931700000-73f360589a13230eea7a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0908600300-b1eccda8ebae8b9e4cc1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-bdb826f9c3cbc09eff9b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019800000-00ad56b6b6a3bb4516e6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-667064ca470a5c341974	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000j-0509700500-8766cb874f927ed5a795	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-3125e04c09a14c62f22a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0019700000-78c46ea4b4f562757e56	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000b-0009400000-94b845d2c8d082b9484c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-6bac7b7f631dfc074a0c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0920000000-49c9d4fb9b57a59f45a5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-572f0b1bd59f71ab3c5f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-d2ede6a2e7183f1c32a3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000100900-78554afbc26abe26af35	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0930000000-274da0a01c651b791733	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0003900000-55939cda9e14fc582757	2012-08-31	View Spectrum
LC-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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0932110400-f05626487523221c34de	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0930000000-86c3d6490bc3a27e053a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-0980000000-58a46c839e0e520474d7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-8482400900-2c4839849821d2807c57	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-5920100000-b38889aa3d09576e2f3e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7l-3900000000-f7144f6355fab252a516	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0170-1032960400-cdd3286ebb1dea7c4f54	2021-09-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹H] 2D NMR Spectrum (predicted)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, H₂O, predicted)	Not Available	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood
Feces

Tissue Locations

Erythrocyte
Liver
Placenta
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Citric Acid Cycle
Glycerol Phosphate Shuttle		Not Available
Riboflavin Metabolism
Aspartate Metabolism
Canavan Disease		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.061 (0.044-0.078) uM	Adult (>18 years old)	Female	Normal	18230968	details
Blood	Detected and Quantified	0.078 +/- 0.054 uM	Adolescent (13-18 years old)	Female	Normal	10197568	details
Blood	Detected and Quantified	0.075 (0.056-0.097) uM	Adult (>18 years old)	Both	Normal	12194936	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.031 +/- 0.01 uM	Children (1-13 years old)	Both	Malnutrition (type kwashiorkor and marasmus)	10731506	details
Blood	Detected and Quantified	0.048 +/- 0.023 uM	Adolescent (13-18 years old)	Female	Anorexia nervosa	10197568	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Anorexia nervosa
Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

606788 (Anorexia nervosa)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB03147

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Flavin_adenine_dinucleotide

METLIN ID

6106

PubChem Compound

643975

PDB ID

Not Available

ChEBI ID

16238

Food Biomarker Ontology

Not Available

VMH ID

FAD

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Flatz G, Simmersbach F: Flavin adenine dinucleotide concentration in erythrocytes with normal and deficient glucose-6-phosphate dehydrogenase. Klin Wochenschr. 1970 Sep 1;48(17):1071-2. [PubMed:5523465 ]
Zempleni J: Determination of riboflavin and flavocoenzymes in human blood plasma by high-performance liquid chromatography. Ann Nutr Metab. 1995;39(4):224-6. [PubMed:8546438 ]
Becker K, Wilkinson AR: Flavin adenine dinucleotide levels in erythrocytes of very low birthweight infants under vitamin supplementation. Biol Neonate. 1993;63(2):80-5. [PubMed:8448258 ]
Lisowsky T, Lee JE, Polimeno L, Francavilla A, Hofhaus G: Mammalian augmenter of liver regeneration protein is a sulfhydryl oxidase. Dig Liver Dis. 2001 Mar;33(2):173-80. [PubMed:11346147 ]
Cimino JA, Jhangiani S, Schwartz E, Cooperman JM: Riboflavin metabolism in the hypothyroid human adult. Proc Soc Exp Biol Med. 1987 Feb;184(2):151-3. [PubMed:3809170 ]
Kodentsova VM, Vrzhesinskaia OA, Alekseeva IA, Spirichev VB: [Comparison of biochemical criteria for supplying the human body with riboflavin]. Vopr Med Khim. 1991 Sep-Oct;37(5):76-9. [PubMed:1759408 ]
Lopez-Anaya A, Mayersohn M: Quantification of riboflavin, riboflavin 5'-phosphate and flavin adenine dinucleotide in plasma and urine by high-performance liquid chromatography. J Chromatogr. 1987 Dec 25;423:105-13. [PubMed:3443641 ]
Van Binsbergen CJ, Odink J, Van den Berg H, Koppeschaar H, Coelingh Bennink HJ: Nutritional status in anorexia nervosa: clinical chemistry, vitamins, iron and zinc. Eur J Clin Nutr. 1988 Nov;42(11):929-37. [PubMed:3074921 ]
Mohrenweiser HW, Novotny JE: ACP1GUA-1--a low-activity variant of human erythrocyte acid phosphatase: association with increased glutathione reductase activity. Am J Hum Genet. 1982 May;34(3):425-33. [PubMed:7081221 ]
Gianazza E, Vergani L, Wait R, Brizio C, Brambilla D, Begum S, Giancaspero TA, Conserva F, Eberini I, Bufano D, Angelini C, Pegoraro E, Tramontano A, Barile M: 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. Electrophoresis. 2006 Mar;27(5-6):1182-98. [PubMed:16470778 ]
Cimino JA, Noto RA, Fusco CL, Cooperman JM: Riboflavin metabolism in the hypothyroid newborn. Am J Clin Nutr. 1988 Mar;47(3):481-3. [PubMed:3348160 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 166 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Dihydrolipoyl dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:: DLD
Uniprot ID:: P09622
Molecular weight:: 54176.91

Enzyme Details

2. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Reactions

Palmityl-CoA + FAD → (2E)-Hexadecenoyl-CoA + FADH	details
Octanoyl-CoA + FAD → (2E)-Octenoyl-CoA + FADH	details
Lauroyl-CoA + FAD → (2E)-Dodecenoyl-CoA + FADH	details
Tetradecanoyl-CoA + FAD → (2E)-Tetradecenoyl-CoA + FADH	details
Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details
Decanoyl-CoA (n-C10:0CoA) + FAD → (2E)-Decenoyl-CoA + FADH	details

Enzyme Details

3. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Reactions

Butyryl-CoA + FAD → FADH + Crotonoyl-CoA	details
Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details

Enzyme Details

4. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Reactions

Propionyl-CoA + FAD → FADH + Acrylyl-CoA	details
Butyryl-CoA + FAD → FADH + Crotonoyl-CoA	details
Palmityl-CoA + FAD → (2E)-Hexadecenoyl-CoA + FADH	details
Octanoyl-CoA + FAD → (2E)-Octenoyl-CoA + FADH	details
Lauroyl-CoA + FAD → (2E)-Dodecenoyl-CoA + FADH	details
Tetradecanoyl-CoA + FAD → (2E)-Tetradecenoyl-CoA + FADH	details
Isovaleryl-CoA + FAD → 3-Methylcrotonyl-CoA + FADH	details
Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details
Decanoyl-CoA (n-C10:0CoA) + FAD → (2E)-Decenoyl-CoA + FADH	details

Enzyme Details

5. NADH-ubiquinone oxidoreductase chain 1

General function:: Involved in oxidation reduction
Specific function:: Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:: MT-ND1
Uniprot ID:: P03886
Molecular weight:: 35660.055

Enzyme Details

6. NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 1

General function:: Involved in NADH dehydrogenase activity
Specific function:: Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone
Gene Name:: NDUFB1
Uniprot ID:: O75438
Molecular weight:: 6961.2

Enzyme Details

7. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1

General function:: Involved in catalytic activity
Specific function:: Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:: ENPP1
Uniprot ID:: P22413
Molecular weight:: 104923.58

Reactions

FAD + Water → Adenosine monophosphate + Flavin mononucleotide	details

Enzyme Details

8. NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial

General function:: Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:: Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:: NDUFS2
Uniprot ID:: O75306
Molecular weight:: 51851.59

Enzyme Details

9. Succinate dehydrogenase cytochrome b560 subunit, mitochondrial

General function:: Involved in succinate dehydrogenase activity
Specific function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:: SDHC
Uniprot ID:: Q99643
Molecular weight:: 16650.185

Enzyme Details

10. Peroxisomal sarcosine oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Metabolizes sarcosine, L-pipecolic acid and L-proline.
Gene Name:: PIPOX
Uniprot ID:: Q9P0Z9
Molecular weight:: 44065.515

Only showing the first 10 proteins. There are 166 proteins in total.

Show all enzymes and transporters

Showing metabocard for FAD (HMDB0001248)

MOL for HMDB0001248 (FAD)

SDF for HMDB0001248 (FAD)

3D-SDF for HMDB0001248 (FAD)

PDB for HMDB0001248 (FAD)

SMILES for HMDB0001248 (FAD)

INCHI for HMDB0001248 (FAD)

Structure for HMDB0001248 (FAD)

3D Structure for HMDB0001248 (FAD)

Enzymes

Reactions

Reactions

Reactions

Reactions