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6-Biopterin

Names

[ CAS No. ]:
22150-76-1

[ Name ]:
6-Biopterin

[Synonym ]:
D-erythro-Biopterin
2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone
4(1H)-Pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-
2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(8H)-one
biopterin
MFCD00036787
1,2-Propanediol, 1-(1,2-dihydro-4-hydroxy-2-imino-6-pteridinyl)-, (1R,2S)-
L-Biopterin
Pterin HB2
pterinhb2
(-)-Biopterin
L-Erythro-Biopterin
6-BIOPTERIN
EINECS 244-807-8
(1R,2S)-1-(4-Hydroxy-2-imino-1,2-dihydro-6-pteridinyl)-1,2-propanediol
[S-(R*,S*)]-2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone
(1'S,2'R)-Biopterin
Pterin H B2

Biological Activity

[Description]:

6-Biopterin (L-Biopterin), a pterin derivative, is a NO synthase cofactor.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> NO Synthase
Natural Products >> Saccharides and Glycosides
Research Areas >> Cancer
Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite


[In Vitro]

6-biopterin is extremely cytotoxic to human melanocytes under in vitro conditions. Thioredoxin reductase has the capacity to reduce 6-biopterin to q-BH2 where further reduction to 6-BH4 follows via dihydropteridine reductase or reduced glutathione. (6R)5,6,7,8 tetrahydrobiopterin undergoes redox-cycling by its oxidation to quinonoid dihydrobiopterin and to 6-biopterin through consecutive two electron oxidation reactions[1].

[References]

[1]. Schallreuter KU, et al. Cytotoxicity of 6-biopterin to human melanocytes. Biochem Biophys Res Commun. 1994 Oct 14;204(1):43-8.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | L-NAME HCl | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
563.4±60.0 °C at 760 mmHg

[ Melting Point ]:
>210°C dec.

[ Molecular Formula ]:
C9H11N5O3

[ Molecular Weight ]:
237.215

[ Flash Point ]:
294.5±32.9 °C

[ Exact Mass ]:
237.086182

[ PSA ]:
138.01000

[ LogP ]:
-3.84

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.822

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UO3506000
CHEMICAL NAME :
4(3H)-Pteridinone, 2-amino-6-(L-erythro-1,2-dihydroxypropyl)-
CAS REGISTRY NUMBER :
22150-76-1
LAST UPDATED :
199509
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C9-H11-N5-O3
MOLECULAR WEIGHT :
237.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
879 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in spleen weight

MUTATION DATA

TEST SYSTEM :
Insect - Drosophila melanogaster
DOSE/DURATION :
10 ug/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 128,147,1984

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UO3506000

[ HS Code ]:
2933990090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Circulating tetrahydrobiopterin as a novel biomarker for abdominal aortic aneurysm.

Am. J. Physiol. Heart Circ. Physiol. 307(11) , H1559-64, (2014)

Rupture of abdominal aortic aneurysm (AAA) is unpredictable and lethal. A clinically valid biomarker to monitor the disease has not been available. Based on our recent discoveries that uncoupled endot...

Phenylalanine hydroxylase: function, structure, and regulation.

IUBMB Life 65(4) , 341-9, (2013)

Mammalian phenylalanine hydroxylase (PAH) catalyzes the rate-limiting step in the phenylalanine catabolism, consuming about 75% of the phenylalanine input from the diet and protein catabolism under ph...

Communication between the zinc and tetrahydrobiopterin binding sites in nitric oxide synthase.

Biochemistry 53(25) , 4216-23, (2014)

The nitric oxide synthase (NOS) dimer is stabilized by a Zn(2+) ion coordinated to four symmetry-related Cys residues exactly along the dimer 2-fold axis. Each of the two essential tetrahydrobiopterin...


More Articles


Related Compounds

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