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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11N5O4
Molecular Weight 253.2147
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEOPTERIN, D-THREO-

SMILES

NC1=NC2=C(N=C(C=N2)[C@@H](O)[C@H](O)CO)C(=O)N1

InChI

InChIKey=BMQYVXCPAOLZOK-INEUFUBQSA-N
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)/t4-,6-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H11N5O4
Molecular Weight 253.2147
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1782220 | https://www.drugbank.ca/drugs/DB02385 | https://www.ncbi.nlm.nih.gov/pubmed/5680748

D-(+)-Neopterin (D-monapterin, Monapterin) is a pteridine derivative, naturally found in Dictyostelium discoideum and in the urine of cancer patients.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.6 null [pIC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Reduced pteridine derivatives induce apoptosis in PC12 cells.
2002-07
YKL-40 is elevated in cerebrospinal fluid from patients with purulent meningitis.
2002-05
Serum neopterin and activity of coronary artery disease.
2002-04-27
Pteridine derivatives as modulators of oxidative stress.
2002-04
Immune monitoring in organ transplantation using neopterin.
2002-04
Neopterin as a marker for immune system activation.
2002-04
Inflammatory responses in Ebola virus-infected patients.
2002-04
Thoracoscopy versus thoracotomy: a prospective comparison of trauma and quality of life.
2002-04
Procalcitonin and neopterin as indicators of infection in critically ill patients.
2002-04
Plasma levels of soluble CD27: a simple marker to monitor immune activation during potent antiretroviral therapy in HIV-1-infected subjects.
2002-03
Reaction mechanism of GTP cyclohydrolase I: single turnover experiments using a kinetically competent reaction intermediate.
2002-02-22
Stressful life events and skin diseases: an additional perspective from research on psychosomatic dynamics in systemic lupus erythematosus.
2002-02-15
Screening for tetrahydrobiopterin deficiency among hyperphenylalaninemia patients in Southern China.
2002-02
[Role of pathological delayed-type hypersensitivity in chronic fatigue syndrome: importance of the evaluation of lymphocyte activation by flow cytometry and the measurement of urinary neopterin].
2002-02
Dopa-responsive dystonia -- the story so far.
2002-02
Local immunostimulation induced by intravesical administration of autologous interferon-gamma-activated macrophages in patients with superficial bladder cancer.
2002-02
Treatment of Crohn's disease with recombinant human interleukin 10 induces the proinflammatory cytokine interferon gamma.
2002-02
Intraarterial chemotherapy of malignant melanoma metastatic to the liver.
2002-01-30
Relationships between serum markers of monocyte/macrophage activation in type 1 Gaucher's disease.
2002-01
Serum neopterin monitoring and vitamin E-modified, regenerated hemodialyzer membrane influence on biocompatibility.
2002-01
Prolonged intrathecal release of soluble Fas following severe traumatic brain injury in humans.
2002-01
Decreased plasma tetrahydrobiopterin in pregnant women is caused by impaired 6-pyruvoyl tetrahydropterin synthase activity.
2002-01
Factors influencing serum neopterin concentrations in a population of blood donors.
2002
Influence of cytokines tumor necrosis factor-alpha and interferon-gamma on signaling cascades associated with apoptosis in rat PC12 cells.
2001-12-28
Monitoring of immune activation using biochemical changes in a porcine model of cardiac arrest.
2001-12
Secondary prevention with fluvastatin decreases levels of adhesion molecules, neopterin and C-reactive protein.
2001-12
Increased blood-brain barrier permeability in neuro-asymptomatic HIV-1-infected individuals--correlation with cerebrospinal fluid HIV-1 RNA and neopterin levels.
2001-12
Complement binding to erythrocytes is associated with macrophage activation and reduced haemoglobin in Plasmodium falciparum malaria.
2001-11-15
Monocyte function and plasma levels of interleukin-8 in acute ischemic stroke.
2001-11-15
Randomized pilot trial of betaINF1a (Avonex) in patients with inclusion body myositis.
2001-11-13
Chemokines CXCL10 and CCL2: differential involvement in intrathecal inflammation in multiple sclerosis.
2001-11
Aqueous extracts of Crinum latifolium (L.) and Camellia sinensis show immunomodulatory properties in human peripheral blood mononuclear cells.
2001-11
Perioperative treatment with human recombinant interferon-gamma: a randomized double-blind clinical trial.
2001-11
Dehydroepiandrosterone, ageing and immune activation.
2001-11
Low serum levels of CD44, CD44v6, and neopterin indicate immune dysfunction in chronic pancreatitis.
2001-11
Tetrahydrobiopterin deficiencies without hyperphenylalaninemia: diagnosis and genetics of dopa-responsive dystonia and sepiapterin reductase deficiency.
2001-10-11
Biochemical profile and survival in nonagenarians.
2001-10
Neopterin measurement in clinical diagnosis.
2001-10
[Changes in serum neopterin levels in patients after trauma].
2001-09
Protection of U937 cells from free radical damage by the macrophage synthesized antioxidant 7,8-dihydroneopterin.
2001-09
Drug level monitoring: the next advance in diagnostics.
2001-08
Is hyperhomocysteinemia due to the oxidative depletion of folate rather than to insufficient dietary intake?
2001-08
[The predictive value of serum neopterin for multiple organ dysfunction syndrome in extensively burned patients].
2001-06
Elevated nitric oxide/peroxynitrite mechanism for the common etiology of multiple chemical sensitivity, chronic fatigue syndrome, and posttraumatic stress disorder.
2001-03
Cytokines and chronic fatigue syndrome.
2001-03
[Hepatocytes growth factor (HGF), leptin, neopterin serum concentrations in patients with chronic hepatitis C].
2001
The role of immune activation in endotoxin-induced atherogenesis.
2001
HIV infection and aging: enhanced Interferon- and Tumor Necrosis Factor-alpha production by the CD8+ CD28- T subset.
2001
Clinical utility of selected disease activity markers in patients with systemic lupus erythematosus.
2001
[The influence of daily psychosocial stressors and associated emotions on the dynamic course of urine cortisol and urine neopterin in systemic lupus erythematosus: Experience taken from two "integrative single-case studies"].
2001
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:50:42 GMT 2025
Edited
by admin
on Mon Mar 31 22:50:42 GMT 2025
Record UNII
26C7CRZ5LJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
D-MONAPTERIN
Preferred Name English
NEOPTERIN, D-THREO-
Common Name English
D-THREO-NEOPTERIN
Common Name English
MONAPTERIN
Common Name English
NEOPTERIN D-THREO-FORM [MI]
Common Name English
D-THREO-MONAPTERIN
Common Name English
MONAPTERIN, D-(-)-
Common Name English
4(1H)-PTERIDINONE, 2-AMINO-6-((1R,2R)-1,2,3-TRIHYDROXYPROPYL)-
Systematic Name English
Code System Code Type Description
CAS
10162-32-0
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY
FDA UNII
26C7CRZ5LJ
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY
CHEBI
49751
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY
DRUG BANK
DB02385
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID30276498
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY
MERCK INDEX
m7817
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY Merck Index
PUBCHEM
135460965
Created by admin on Mon Mar 31 22:50:42 GMT 2025 , Edited by admin on Mon Mar 31 22:50:42 GMT 2025
PRIMARY