Showing Metabocard for 2'-deoxyguanosine (BASm0000871)
| Common Name | 2'-deoxyguanosine | ||||||||||||||||||||||||||||||||||||
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| Description | Deoxyguanosine, also known as dG, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2’. Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. Deoxyguanosine is one of the four deoxyribonucleosides that make up DNA. Deoxyguanosine exists in all living species, ranging from bacteria to plants to humans. Deoxyguanosine participates in a number of enzymatic reactions. In particular, deoxyguanosine can be biosynthesized from 2'-deoxyguanosine 5'-monophosphate through the enzyme known as cytosolic purine 5'-nucleotidase. In addition, deoxyguanosine can be converted into 2'-deoxyguanosine 5'-monophosphate (dGMP); which is mediated by the enzyme deoxyguanosine kinase. Deoxyguanosine is involved in the rare, inherited metabolic disorder called the purine nucleoside phosphorylase deficiency (PNP deficiency). In particular PNP deficiency is characterized by elevated levels of dGTP (deoxyguanosine triphosphate). PNP accounts for approximately 4% of patients with severe combined immunodeficiency (PMID: 1931007 ). PNP-deficient patients suffer from recurrent infections, usually beginning in the first year of life. Two thirds of patients have evidence of neurologic disorders with spasticity, developmental delay and mental retardation. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-hydroxy-deoxyguanosine is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion. | ||||||||||||||||||||||||||||||||||||
| Structure | |||||||||||||||||||||||||||||||||||||
| Molecular Formula | C10H13N5O4 | ||||||||||||||||||||||||||||||||||||
| Average Mass | 267.24130 | ||||||||||||||||||||||||||||||||||||
| Monoisotopic Mass | 267.09675 | ||||||||||||||||||||||||||||||||||||
| IUPAC Name | 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one | ||||||||||||||||||||||||||||||||||||
| Traditional Name | 2'-deoxyguanosine | ||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 961-07-9 | ||||||||||||||||||||||||||||||||||||
| SMILES | Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 | ||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1 | ||||||||||||||||||||||||||||||||||||
| InChI Key | YKBGVTZYEHREMT-KVQBGUIXSA-N | ||||||||||||||||||||||||||||||||||||
| CHEBI ID | CHEBI:17172 | ||||||||||||||||||||||||||||||||||||
| HMDB ID | HMDB0000085 | ||||||||||||||||||||||||||||||||||||
| Pathways |
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| State | Not Available | ||||||||||||||||||||||||||||||||||||
| Water Solubility | 1.15e+01 g/l | ||||||||||||||||||||||||||||||||||||
| logP | -1.75 | ||||||||||||||||||||||||||||||||||||
| logS | -1.37 | ||||||||||||||||||||||||||||||||||||
| pKa (Strongest Acidic) | 10.16 | ||||||||||||||||||||||||||||||||||||
| pKa (Strongest Basic) | 1.83 | ||||||||||||||||||||||||||||||||||||
| Hydrogen Acceptor Count | 7 | ||||||||||||||||||||||||||||||||||||
| Hydrogen Donor Count | 4 | ||||||||||||||||||||||||||||||||||||
| Polar Surface Area | 134.99 Ų | ||||||||||||||||||||||||||||||||||||
| Rotatable Bond Count | 2 | ||||||||||||||||||||||||||||||||||||
| Physiological Charge | 0 | ||||||||||||||||||||||||||||||||||||
| Formal Charge | 0 | ||||||||||||||||||||||||||||||||||||
| Refractivity | 63.11 m³·mol⁻¹ | ||||||||||||||||||||||||||||||||||||
| Polarizability | 25.22 |