FAD (C27H33N9O15P2): structure, properties and hazards

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-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
Synonyms: flavin adenine dinucleotide, riboflavin cofactor, Flavin-adenine dinucleotide
+ 36 more
Flavine-adenine dinucleotide, Flavine adenosine diphosphate, Adenine-riboflavin dinucleotide, Riboflavin 5'-adenosine diphosphate, Flavin adenin dinucleotide, Flavine adenine dinucleotide, ZC44YTI8KK, CHEBI:16238, NSC-112207, ADENOSINE 5'-(TRIHYDROGEN PYROPHOSPHATE), 5'-5'-ESTER with RIBOFLAVINE, [[(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-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate, DTXSID4048307, Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine, Riboflavin 5'-(trihydrogen diphosphate), P'->5'-ester with adenosine, Riboflavin 5'-(trihydrogen diphosphate), P'-5'-ester with adenosine, RIBOFLAVINE 5'-(TRIHYDROGEN DIPHOSPHATE) 5'->5'-ESTER WITH ADENOSINE, (((((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-2H,3H,4H,10H-benzo(g)pteridin-10-yl)-2,3,4-trihydroxypentyl)oxy))phosphinic acid, (((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-dioxobenzo(g)pteridin-10-yl)-2,3,4-trihydroxypentyl) hydrogen phosphate, [({[(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-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid, RefChem:140623, Dinucleotide, Flavin-Adenine, DTXCID6028282, CHEBI:24040, 205-663-1, Adenine-flavin dinucleotide, Adenine-flavine dinucleotide, Adenine-riboflavin dinuceotide, Riboflavin-adenine dinucleotide, Riboflavine-adenine dinucleotide, Flanin F, Isoalloxazine-adenine dinucleotide, Flavinat, Adenine-riboflavine dinucleotide, Flamitajin B, MFCD00041835, NSC 112207
Molecular formula: C₂₇H₃₃N₉O₁₅P₂
Empirical formula: C₂₇H₃₃N₉O₁₅P₂
Molecular weight: 785.5 g/mol
Exact mass: 785.15714
CAS number: 146-14-5
PubChem CID: 643975
Canonical SMILES: CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)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=NC(=O)NC(=O)C3=N2)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/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
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 53
Rings: 6
Aromatic rings: 3
Fraction sp³ carbons (Fsp3): 0.44
H-bond donors: 9
H-bond acceptors: 19 computed here · PubChem 20
Rotatable bonds: 13
TPSA (Å²): 362.9 computed here · PubChem 356
Formal charge: 0
XLogP3: -5 PubChem
Complexity: 1560 PubChem
Stereocenters: 7 defined, 2 undefinedCIP: C16: S · C18: S · C20: R · P24: undefined · P28: undefined · C33: R · C35: R · C46: R · C48: 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

C41.28%
H4.23%
N16.05%
O30.55%
P7.89%

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: -2.42 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.65 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 5.27 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 785.56
log P ≤ 5 (Crippen): -2.42
H-bond donors ≤ 5: 9
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: Alfa Chemistry, Achemtek, Ambeed.

Always read the supplier’s safety data sheet before working with it.

Spectra

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 Europe · Linked only · via PubChem · retrieved 2026-10-14
[3]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.

Similar structures

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.