Physicochemical Properties
| Molecular Formula | C9H11N5O3 |
| Molecular Weight | 237.21 |
| Exact Mass | 237.086 |
| CAS # | 22150-76-1 |
| PubChem CID | 135403659 |
| Appearance | White to light yellow solid powder |
| Density | 1.9±0.1 g/cm3 |
| Boiling Point | 563.4±60.0 °C at 760 mmHg |
| Melting Point | >210°C dec. |
| Flash Point | 294.5±32.9 °C |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
| Index of Refraction | 1.822 |
| LogP | -3.84 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 17 |
| Complexity | 348 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C[C@@H]([C@@H](C1=CN=C2C(=N1)C(=O)NC(=N2)N)O)O |
| InChi Key | LHQIJBMDNUYRAM-DZSWIPIPSA-N |
| InChi Code | InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1 |
| Chemical Name | 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3H-pteridin-4-one |
| Synonyms | NSC-339699 NSC 339699 L-Biopterin |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | 6-Biopterin is highly cytotoxic to human melanocytes when cultured in vitro. 6-biopterin can be reduced by thioredoxin reductase to q-BH2, which is subsequently reduced to 6-BH4 by reduced glutathione or dihydropterin reductase. A continuous two-electron oxidation reaction converts (6R)5,6,7,8 tetrahydrobiopterin to quinone dihydrobiopterin and 6-biopterin, completing a redox cycle [1]. |
| References |
[1]. Cytotoxicity of 6-biopterin to human melanocytes. Biochem Biophys Res Commun. 1994 Oct 14;204(1):43-8. |
| Additional Infomation |
L-erythro-biopterin is a biopterin in which the 1,2-dihydroxypropyl group has (1R,2S)-configuration; naturally occurring form. It is an enantiomer of a D-erythro-biopterin. Pterin derivatives based on 2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone. Biopterins are natural products that have been considered as growth factors for some insects. Biopterins are cofactors for the AROMATIC AMINO ACID hydroxylases and NITRIC OXIDE SYNTHASE. Deficiencies in BIOPTERINS metabolism (e.g., lowered TETRAHYDROBIOPTERIN) are associated with neurological deterioration (e.g., HYPERPHENYLALANINAEMIA). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~12.5 mg/mL (~52.69 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 1 mg/mL (4.22 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1 mg/mL (4.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2157 mL | 21.0784 mL | 42.1567 mL | |
| 5 mM | 0.8431 mL | 4.2157 mL | 8.4313 mL | |
| 10 mM | 0.4216 mL | 2.1078 mL | 4.2157 mL |