FAD (CHEBI:16238)

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CHEBI:16238 - FAD

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ChEBI Name	FAD

ChEBI ID	CHEBI:16238

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

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42388, CHEBI:4956, CHEBI:13315, CHEBI:21125

Supplier Information	ChemicalBook:CB0428149, eMolecules:1935773, ZINC000000119983

Download	Molfile XML SDF

more structures >>

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86 91 0 0 1 0 999 V2000

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1.4576 -1.2981 -0.3247 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8415 -3.2600 -1.6111 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5677 -0.9410 -0.9832 O 0 0 0 0 0 0 0 0 0 0 0 0

3.6382 -0.1051 -0.4526 P 0 0 1 0 0 0 0 0 0 0 0 0

4.7072 0.0129 -1.4310 O 0 0 0 0 0 0 0 0 0 0 0 0

3.0743 1.1968 -0.1703 O 0 0 0 0 0 0 0 0 0 0 0 0

4.1057 -0.6686 0.7912 O 0 0 0 0 0 0 0 0 0 0 0 0

5.9680 0.7236 -1.2849 P 0 0 1 0 0 0 0 0 0 0 0 0

5.7305 2.1032 -0.8675 O 0 0 0 0 0 0 0 0 0 0 0 0

6.8132 0.0089 -0.3552 O 0 0 0 0 0 0 0 0 0 0 0 0

6.6240 0.7078 -2.5667 O 0 0 0 0 0 0 0 0 0 0 0 0

6.5315 2.9548 -0.2217 C 0 0 0 0 0 0 0 0 0 0 0 0

5.7746 4.2296 0.2233 C 0 0 1 0 0 0 0 0 0 0 0 0

4.6599 3.9484 1.0819 O 0 0 0 0 0 0 0 0 0 0 0 0

6.6474 5.2187 1.0347 C 0 0 2 0 0 0 0 0 0 0 0 0

4.3310 5.1575 1.7861 C 0 0 2 0 0 0 0 0 0 0 0 0

5.7324 5.6592 2.1967 C 0 0 2 0 0 0 0 0 0 0 0 0

7.1006 6.2858 0.2033 O 0 0 0 0 0 0 0 0 0 0 0 0

3.4190 4.9957 2.8855 N 0 0 0 0 0 0 0 0 0 0 0 0

5.7653 7.0618 2.4525 O 0 0 0 0 0 0 0 0 0 0 0 0

2.7882 3.8820 3.3052 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0181 5.9751 3.7285 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0522 4.2172 4.4436 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7752 2.6093 2.8294 N 0 0 0 0 0 0 0 0 0 0 0 0

2.1953 5.5250 4.6902 N 0 0 0 0 0 0 0 0 0 0 0 0

1.3387 3.2075 5.1135 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0511 1.6459 3.4596 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3540 1.9530 4.5875 N 0 0 0 0 0 0 0 0 0 0 0 0

0.6951 3.4422 6.2285 N 0 0 0 0 0 0 0 0 0 0 0 0

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-0.9763 -2.0323 -0.4362 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.7969 -2.4912 0.5412 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3762 -1.9723 -1.2056 C 0 0 1 0 0 0 0 0 0 0 0 0

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3.8651 5.8619 1.0862 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0396 5.1491 3.1163 H 0 0 0 0 0 0 0 0 0 0 0 0

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6.6960 7.2580 2.6904 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3027 6.9551 3.6698 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 2 1 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

2 5 1 0 0 0 0

2 6 2 0 0 0 0

3 7 4 0 0 0 0

3 8 4 0 0 0 0

4 51 1 0 0 0 0

5 9 2 0 0 0 0

5 10 1 0 0 0 0

6 11 1 0 0 0 0

7 12 4 0 0 0 0

8 13 4 0 0 0 0

51 53 1 0 0 0 0

51 14 1 0 0 0 0

10 15 1 0 0 0 0

10 16 2 0 0 0 0

11 17 2 0 0 0 0

12 18 4 0 0 0 0

13 19 1 0 0 0 0

53 55 1 0 0 0 0

53 20 1 0 0 0 0

18 21 1 0 0 0 0

55 22 1 0 0 0 0

55 23 1 0 0 0 0

22 24 1 0 0 0 0

24 25 1 0 0 0 0

25 26 1 0 0 0 0

25 27 1 0 0 0 0

25 28 2 0 0 0 0

26 29 1 0 0 0 0

29 30 1 0 0 0 0

29 31 1 0 0 0 0

29 32 2 0 0 0 0

30 33 1 0 0 0 0

34 33 1 0 0 0 0

34 35 1 0 0 0 0

34 36 1 0 0 0 0

35 37 1 0 0 0 0

36 38 1 0 0 0 0

36 39 1 0 0 0 0

37 40 1 0 0 0 0

38 41 1 0 0 0 0

40 42 4 0 0 0 0

40 43 4 0 0 0 0

42 44 4 0 0 0 0

42 45 4 0 0 0 0

43 46 4 0 0 0 0

44 47 4 0 0 0 0

45 48 4 0 0 0 0

47 49 4 0 0 0 0

47 50 1 0 0 0 0

7 9 1 0 0 0 0

11 15 1 0 0 0 0

13 18 4 0 0 0 0

37 38 1 0 0 0 0

44 46 4 0 0 0 0

48 49 4 0 0 0 0

51 52 1 0 0 0 0

53 54 1 0 0 0 0

55 56 1 0 0 0 0

4 57 1 0 0 0 0

4 58 1 0 0 0 0

8 59 1 0 0 0 0

12 60 1 0 0 0 0

14 61 1 0 0 0 0

15 62 1 0 0 0 0

19 63 1 0 0 0 0

19 64 1 0 0 0 0

19 65 1 0 0 0 0

20 66 1 0 0 0 0

21 67 1 0 0 0 0

21 68 1 0 0 0 0

21 69 1 0 0 0 0

22 70 1 0 0 0 0

22 71 1 0 0 0 0

23 72 1 0 0 0 0

27 73 1 0 0 0 0

31 74 1 0 0 0 0

33 75 1 0 0 0 0

33 76 1 0 0 0 0

34 77 1 0 0 0 0

36 78 1 0 0 0 0

37 79 1 0 0 0 0

38 80 1 0 0 0 0

39 81 1 0 0 0 0

41 82 1 0 0 0 0

43 83 1 0 0 0 0

48 84 1 0 0 0 0

50 85 1 0 0 0 0

50 86 1 0 0 0 0

M END): 22 ms

reading 86 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

86 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C27H33N9O15P2

Net Charge

Average Mass

785.55010

Monoisotopic Mass

785.15714

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,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1

InChIKey

VWWQXMAJTJZDQX-UYBVJOGSSA-N

SMILES

Cc1cc2nc3c(nc(=O)[nH]c3=O)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)n3cnc4c(N)ncnc34)c2cc1C

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). (via flavin adenine dinucleotide ) prosthetic group A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity. water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via B vitamin )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	FAD (CHEBI:16238) has role Escherichia coli metabolite (CHEBI:76971) FAD (CHEBI:16238) has role cofactor (CHEBI:23357) FAD (CHEBI:16238) has role human metabolite (CHEBI:77746) FAD (CHEBI:16238) has role mouse metabolite (CHEBI:75771) FAD (CHEBI:16238) has role prosthetic group (CHEBI:26348) FAD (CHEBI:16238) is a flavin adenine dinucleotide (CHEBI:24040) FAD (CHEBI:16238) is a vitamin B₂ (CHEBI:176838) FAD (CHEBI:16238) is conjugate acid of FAD(3−) (CHEBI:57692)

Incoming	FAD(3−) (CHEBI:57692) is conjugate base of FAD (CHEBI:16238)

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)

Synonyms	Sources
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine	ChemIDplus
adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate]	ChEBI
FAD	KEGG COMPOUND
Flavin adenine dinucleotide	KEGG COMPOUND
FLAVIN-ADENINE DINUCLEOTIDE	PDBeChem
Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine	ChemIDplus
Riboflavin 5'-adenosine diphosphate	ChemIDplus

Manual Xrefs	Databases
C00001500	KNApSAcK
C00016	KEGG COMPOUND
D00005	KEGG DRUG
DB03147	DrugBank
FAD	PDBeChem
MOL000039	COMe
View more database links

Registry Numbers	Types	Sources
108834	Gmelin Registry Number	Gmelin
1208946	Beilstein Registry Number	Beilstein
146-14-5	CAS Registry Number	KEGG COMPOUND
146-14-5	CAS Registry Number	ChemIDplus

Citations	Types	Sources
24643482	PubMed citation	Europe PMC
25108762	PubMed citation	Europe PMC

Last Modified

20 July 2021

CHEBI:16238 - FAD

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