FADH2
Athanor · official
C27H35N9O15P2 · 787.6 g/mol
IUPAC name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-1,5-dihydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
Also called reduced FAD, dihydroflavin adenine dinucleotide
Names and identifiers
- IUPAC name
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-1,5-dihydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
- Synonyms
- reduced FAD, dihydroflavin adenine dinucleotide, 1,5-dihydro-FAD
+ 36 more
CHEBI:17877, DTXSID301343006, RefChem:921455, DTXCID701771968, (((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)((((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))phosphinic acid, FADH, DIHYDROFLAVINE-ADENINE DINUCLEOTIDE, Dihydro-FAD, flavin adenine dinucleotide reduced, Reduced flavine adenine dinucleotide, flavin adenine dinucleotide (reduced), [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-1,5-dihydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate, 1,5-dihydro-P-5-ester with adenosine, Adenosine 5-(trihydrogen pyrophosphate), Riboflavin 5'-(trihydrogen diphosphate), 1,5-dihydro-, P'-5'-ester with adenosine, orb3179611, SCHEMBL4363188, [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [[(2R,3S,4S)-5-(7,8-dimethyl-2,, {[(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, C01352, Q27102690, Q27113979, Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv, Benzo[gr]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv, 1,5-dihydro-Riboflavin 5'-(trihydrogen diphosphate) P'->5'-ester with adenosine, Riboflavin 5'-(trihydrogen diphosphate), 1,5-dihydro-, P'-5'-ester with adenosine (9CI), [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name), adenosine 5'-(3-{D-ribo-5-[7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl]-2,3,4-trihydroxypentyl} dihydrogen diphosphate), 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, 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'-{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 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 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)
- Molecular formula
- C27H35N9O15P2
- Empirical formula
- C27H35N9O15P2
- Molecular weight
- 787.6 g/mol
- Exact mass
- 787.17279
- CAS number
- 1910-41-4
- PubChem CID
- 446013
- Canonical SMILES
- CC1=CC2=C(C=C1C)N(C3=C(N2)C(=O)NC(=O)N3)CC(C(C(COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)O
- Isomeric SMILES
- CC1=CC2=C(C=C1C)N(C3=C(N2)C(=O)NC(=O)N3)C[C@@H]([C@@H]([C@@H](COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)O
- 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
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 53
- Rings
- 6
- Aromatic rings
- 4
- Fraction sp³ carbons (Fsp3)
- 0.44
- H-bond donors
- 11
- H-bond acceptors
- 19 computed here · PubChem 21
- Rotatable bonds
- 13
- TPSA (Ų)
- 363.3 computed here · PubChem 356
- Formal charge
- 0
- XLogP3
- -4.8 PubChem
- Complexity
- 1520 PubChem
- Stereocenters
- 7 defined, 2 undefinedCIP: C11: S · C13: S · C15: R · P19: undefined · P23: undefined · C28: R · C30: R · C41: R · C43: S
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C41.18%
- H4.48%
- N16.01%
- O30.47%
- P7.87%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -1.75 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -3.06 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 5.45 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 787.57
- log P ≤ 5 (Crippen): -1.75
- H-bond donors ≤ 5: 11
- H-bond acceptors ≤ 10: 19
Breaks 3 of the four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: EvitaChem, RR Scientific, BenchChem.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Varian · 500 MHz · Water)
- 1H-1H NMRHuman Metabolome Database (HMDB)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- LC-MSMassBank of North America (MoNA) (Quattro_QQQ · positive) · MassBank of North America (MoNA) (Quattro_QQQ · positive) · MassBank of North America (MoNA) (Quattro_QQQ · positive)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [2]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.