Common Name7,8-dihydroneopterin
Description7,8-Dihydroneopterin, also known as dihydroneopterin, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are synthesized in several parts of the body, including the pineal gland. 7,8-Dihydroneopterin is a strong basic compound (based on its pKa). Within humans, 7,8-dihydroneopterin participates in a number of enzymatic reactions. In particular, 7,8-dihydroneopterin can be biosynthesized from sepiapterin; which is catalyzed by the enzyme sepiapterin reductase or carbonyl reductase [NADPH] 1. In humans, 7,8-dihydroneopterin is involved in the metabolic disorder called hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase (PTPS) deficiency. 7,8-Dihydroneopterin is produced by human monocyte-derived macrophages upon stimulation with interferon-gamma. Increased amounts of 7,8-dihydroneopterin in human body fluids are found in many disorders, including viral infections and autoimmune diseases (PMID: 12804528 ).
Structure
Molecular FormulaC9H13N5O4
Average Mass255.23060
Monoisotopic Mass255.09675
IUPAC Name2-amino-6-(1,2,3-trihydroxypropyl)-1,4,7,8-tetrahydropteridin-4-one
Traditional Name2-amino-6-(1,2,3-trihydroxypropyl)-7,8-dihydro-1h-pteridin-4-one
CAS Registry Number1218-98-0
SMILESNc1nc2c(c(=O)[nH]1)N=C([C@H](O)[C@H](O)CO)CN2
InChI IdentifierInChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)/t4-,6+/m1/s1
InChI KeyYQIFAMYNGGOTFB-XINAWCOVSA-N
CHEBI IDCHEBI:17001
HMDB IDHMDB0002275
Pathways
NameSMPDB/PathBank
Pterine Biosynthesis
Dopa-responsive dystonia
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)
Hyperphenylalaninemia due to dhpr-deficiency
Segawa syndrome
Sepiapterin reductase deficiency
StateNot Available
Water Solubility1.86e+00 g/l
logP-2.10
logS-2.14
pKa (Strongest Acidic)7.97
pKa (Strongest Basic)3.22
Hydrogen Acceptor Count9
Hydrogen Donor Count6
Polar Surface Area152.56 Ų
Rotatable Bond Count3
Physiological Charge0
Formal Charge0
Refractivity69.66 m³·mol⁻¹
Polarizability23.99

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