Showing Metabocard for FMNH2 (BASm0002833)

Common Name	Fmnh2
Description	FMNH2 is the reduced form of flavin mononucleotide. It is a substrate of the enzyme FMN reductase (EC 1.5.1.29), an enzyme that catalyzes the chemical reaction FMNH2 + NAD(P)+ <=> FMN + NAD(P)H + H+. Flavin mononucleotide (FMN), or riboflavin-5‚Ä≤-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase. During a catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH‚Ä¢) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers.
Structure
Molecular Formula	C₁₇H₂₁N₄O₉P
Average Mass	456.34380
Monoisotopic Mass	456.10461
IUPAC Name	{[(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}phosphonic acid
Traditional Name	[(2r,3s,4s)-5-{7,8-dimethyl-2,4-dioxo-1h,3h,5h-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxyphosphonic acid
CAS Registry Number	5666-16-0
SMILES	Cc1cc2c(cc1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(=O)([O-])[O-])c1[nH]c(=O)[nH]c(=O)c1N2
InChI Identifier	InChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)/p-2/t11-,12+,14-/m0/s1
InChI Key	YTNIXZGTHTVJBW-SCRDCRAPSA-L
CHEBI ID	CHEBI:57618
HMDB ID	HMDB01142
MiMeDB ID	MMDBc0031153
State	Solid
Water Solubility	6.42e-01 g/l
logP	-0.17
logS	-2.85
pKa (Strongest Acidic)	1.50
pKa (Strongest Basic)	-0.52
Hydrogen Acceptor Count	10
Hydrogen Donor Count	8
Polar Surface Area	200.92 Å²
Rotatable Bond Count	7
Physiological Charge	-2
Formal Charge	0
Refractivity	118.51 m³·mol⁻¹
Polarizability	42.75

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