SynCED: Neopterin

Record Information

Version

1.0

Creation Date

2014-08-29 05:48:16 UTC

Update Date

2026-05-14 19:47:42 UTC

Accession Number

CHEM003122

Identification

Common Name

Neopterin

Class

Small Molecule

Description

Neopterin is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Neopterin is a pteridine derivative present in body fluids; elevated levels result from immune system activation, malignant disease, allograft rejection, and viral infections. (From Stedman, 26th ed) Neopterin also serves as a precursor in the biosynthesis of biopterin.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Food Toxin
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-(D-erythro-1,2,3-Trihydroxypropyl)pterin	HMDB
6-D-erythro-Neopterin	HMDB
D-erythro-Neopterin	HMDB
D-Neopterin	HMDB
Neopterine	HMDB
[S-(R,s)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-ON	HMDB
[S-(R,s)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-one	HMDB
[S-(R,s)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridine-4-one	HMDB
Monapterin	MeSH, HMDB
Neopterin, (r, r)-isomer	MeSH, HMDB
Umanopterin	MeSH, HMDB
Neopterin, (erythro-D)-isomer	MeSH, HMDB
2-amino-6-(1,2,3-Trihydroxypropyl)-4(3H)-pteridinone	MeSH, HMDB
Neopterin, (erythro-L)-isomer	MeSH, HMDB
Neopterin, (threo-D)-isomer	MeSH, HMDB
Neopterin, (threo-L)-isomer	MeSH, HMDB

Chemical Formula

C₉H₁₁N₅O₄

Average Molecular Mass

253.215 g/mol

Monoisotopic Mass

253.081 g/mol

CAS Registry Number

2009-64-5

IUPAC Name

2-amino-6-(1,2,3-trihydroxypropyl)-3,4-dihydropteridin-4-one

Traditional Name

2-amino-6-(1,2,3-trihydroxypropyl)-3H-pteridin-4-one

SMILES

NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1

InChI Identifier

InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)

InChI Key

BMQYVXCPAOLZOK-UHFFFAOYSA-N

Chemical Taxonomy

Description

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 mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Polyol
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Activated T-Lymphocytes
Bone Marrow
Brain
Central Nervous System
Erythrocyte
Fibroblasts
Kidney
Liver
Lymphocyte
Pancreas
Skin
Spleen
T-Lymphocyte

Pathways

Name	SMPDB Link	KEGG Link
Pterine Biosynthesis	SMP00005	map00790
Hyperphenylalaninemia due to dhpr-deficiency	SMP00489	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.26 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.11 m³·mol⁻¹	ChemAxon
Polarizability	23.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as neopterin are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (2). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (3).

Metabolism

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0259432

FooDB ID

FDB112166

Phenol Explorer ID