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D-(+)-NEOPTERIN

D-(+)-NEOPTERIN structure

CAS No:
2009-64-5
Formula:
C9H11N5O4
Chemical Name:
D-(+)-NEOPTERIN
Synonyms:
(+)-NEOPTERIN;2-Amino-6-((1S;3-trihydroxypropyl)pteridin-4(3H)-one;2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone;D-(+)-NEOPTERIN;D(+)-6-(ERYTHRO-1,2,3-TRIHYDROXYPROPYL)PTERIN;D-ERYTHRO-NEOPTERIN;[S-(R*,S*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-one
Categories:
Dyes and Pigments > Pigment

Description

D-(+)-Neopterin, a catabolic product of guanosine triphosphate (GTM), serves as a marker of cellular immune system activation.

Neopterin is under investigation in clinical trial NCT02974192 (Neopterin Effects on Ischemic Stroke).|Neopterin is a pteridine that is a metabolite of guanine triphosphate (GTP) and a precursor for biopterin. Neopterin is released from interferon-gamma (IFNg) stimulated macrophages and dendritic cells (DCs); therefore, urine or serum levels may be used as a marker of immune system activation.|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.

Neopterin is a pyrazino-pyrimidine compound derived from GTP that represents an intermediate product in the synthetic pathway of biopterin and is an essential cofactor in neurotransmitter synthesis. Neopterin is released from macrophages upon immune stimulation with interferon-γ from activated T cells. It is routinely used as a biochemical tool to screen for and monitor the progression of certain diseases accompanied by hyperimmune stimulation.

off-white to yellow solid

D-(+)-Neopterin is a pteridine derivative, naturally found inDictyostelium discoideum. It is found in significant amounts in the urine of cancer patients.

D-(+)-NEOPTERIN Basic Attributes

Molecular Weight：

253.21

Exact Mass：

253.21

BRN：

89070

EC Number：

217-924-7

UNII：

9PLD60N7SO

NCI Thesaurus Code：

C129010

Color/Form：

Light Orange to Light Brown

HScode：

29335990

Characteristics

PSA：

154

XLogP3：

-4.57

Density：

1.3957 (rough estimate)

Melting Point：

>232°C (dec.)

Boiling Point：

396.41°C (rough estimate)

Flash Point：

375.7ºC

Refractive Index：

1.7610 (estimate)

Storage Conditions：

2-8°C

Specific rotation：

D25 +45 ± 3° (c = 0.3 in 0.1N HCl)

PKA：

12.60±0.20(Predicted)

Collision Cross Section：

157.1 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|150.31 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

Critical Temperature & Pressure：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

Marks：

Storage features：

Store at -20°C

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

36/37/38

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone

D-(+)-NEOPTERIN Use and Manufacturing

Precursor in the biosynthesis of Biopterin. First isolated from the pupae of bees.

D-(+)-Neopterin has been used as a NADPH oxidase inhibitor while assessing the ability of NADPH oxidases in breast cancer cells to produce reactive oxygen species (ROS). [NADPH= nicotinamide adenine dinucleotide phosphate]

Computed Properties

Molecular Weight:253.22
XLogP3:-3.5
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:253.08110385
Monoisotopic Mass:253.08110385
Topological Polar Surface Area:154
Heavy Atom Count:18
Complexity:363
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 2009-64-5

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