S154
Sepiapterin
solid
Synonym(s):
S-(−)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone, L-Sepiapterin
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About This Item
Empirical Formula (Hill Notation):
C9H11N5O3
CAS Number:
Molecular Weight:
237.22
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Form:
solid
form
solid
color
yellow
solubility
DMSO: 27 mg/mL, 0.1 M NaOH: 9.8 mg/mL
εmax
6170 at 409 nm in 0.1 M HCl, 7410 at 271 nm in 0.1 M HCl at 1%
storage temp.
−20°C
SMILES string
C[C@H](O)C(=O)C1=NC2=C(NC1)NC(N)=NC2=O
InChI
1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1
InChI key
VPVOXUSPXFPWBN-VKHMYHEASA-N
Gene Information
human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
General description
Sepiapterin, a pteridine derivative, is a stable precursor of tetrahydrobiopterin (BH4). It is a yellow pigment found in sepia mutant of Drosophila melanogaster and lemon Bombyx mori mutant (silkworm).
Application
Sepiapterin can be used to induce sequence-specific photolesions in double-stranded DNA.
Biochem/physiol Actions
Cofactor of nitric oxide synthase; intracellularly converted to tetrahydro-biopterin leading to the stimulation of nitric oxide.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Aidamalia Vargas-Lowman et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(38), 19046-19054 (2019-09-06)
Naturalists have been fascinated for centuries by animal colors and color patterns. While widely studied at the adult stage, we know little about color patterns in the embryo. Here, we study a trait consisting of coloration that is specific to
Isolation, purification, and identification of an important pigment, sepiapterin, from integument of the lemon mutant of the silkworm, Bombyx mori."
JunShan G, et al.
Journal of Insect Science, 13(118) (2013)
Matthieu Legrand et al.
Journal of cardiovascular pharmacology, 58(2), 192-198 (2011-05-13)
Acute kidney injury (AKI) can occur after aortic clamping due to microvascular dysfunction leading to renal hypoxia. In this rat study, we have tested the hypothesis that the administration of the precursor of the nitric oxide synthase essential cofactor tetrahydrobiopterin
Global Trade Item Number
| SKU | GTIN |
|---|---|
| S154-5MG | 04061832992280 |
| S154-25MG | 04061832992273 |