Compound: aldehydo-D-ribose
SMILES: O=C[C@H](O)[C@H](O)[C@H](O)CO
InChIKey: PYMYPHUHKUWMLA-LMVFSUKVSA-N
Synonyms: aldehydo-D-ribose, CHEBI:47014, RefChem:936053, GlyTouCan:G55614WT, G55614WT, aldehydo-D-ribo-pentose;aldehydo-D-ribose, (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal, aldehydo-D-ribo-pentose, d(-)-ribose, MFCD00135453, 34466-20-1, C5H10O5, EINECS 200-059-4, D-Ribose; Ribose, D- (8CI); Ribose; D-(-)-Ribose, BRN 1723081, dl-Ribose, UNII-681HV46001, D-ribose (open form), D-RIBOSE [FHFI], RIBOSE [USP-RS], D-RIBOSE [MI], D-RIBOSE [WHO-DD], D-Ribose, 99.0%+, SCHEMBL22679, 4-01-00-04211 (Beilstein Handbook Reference), D-(-)-Ribose, 98%, orb1302564, orb3139604, SCHEMBL9811639, D-(-)-Ribose, >=98%, D-(-)-Ribose, >=99%, DTXSID101019160, HY-W018772R, Tox21_303971, AC7811, EBC-44226, MFCD06799032, s5544, AKOS016842327, CCG-266199, CS-W019558, DB15073, HY-W018772, MR05196, CAS-50-69-1, D-Ribose(mixture of isomers) (Standard), NCGC00357197-01, SY004436, DB-030333, D-(-)-Ribose, for synthesis, 97-102%, EN300-105204, R-5495, D-(-)-Ribose, Vetec(TM) reagent grade, 99%, F078886, D-(-)-Ribose, plant cell culture tested, BioReagent, D-(-)-Ribose, suitable for cell culture, BioReagent, Q27120759, (2R, 3R, 4R) - 2, 3, 4, 5- Tetrahydroxypentanal, D-(-)-Ribose, >=99.0% (sum of enantiomers, HPLC), E5431ED6-777D-48C4-AE76-2B114FABE2D6, Z1255372712, Ribose, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C5H10O5
molecular_weight: 150.13 g/mol
exact_mass: 150.05282342 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 10
topological_polar_surface_area: 98 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Aldehydo-D-ribose is a D-ribose and an aldehydo-ribose. It is an enantiomer of an aldehydo-L-ribose.", "chebi": null, "chembl": null, "wikipedia": "Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H\u2212(C=O)\u2212(CHOH)4\u2212H.  The naturally occurring form,  d-ribose, is a component of the ribonucleotides from which RNA is built, and so this compound is necessary for coding, decoding, regulation and expression of genes.  It has a structural analog, deoxyribose, which is a similarly essential component of DNA.   l-ribose is an unnatural sugar that was first prepared by Emil Fischer and Oscar Piloty in 1891. It was not until 1909 that Phoebus Levene and Walter Jacobs recognised that  d-ribose was a natural product, the enantiomer of Fischer and Piloty's product, and an essential component of nucleic acids. Fischer chose the name \"ribose\" as it is a partial rearrangement of the name of another sugar, arabinose, of which ribose is an epimer at the 2' carbon; both names also relate to gum arabic, from which arabinose was first isolated and from which they prepared  l-ribose.\n\nLike most sugars, ribose exists as a mixture of cyclic forms in equilibrium with its linear form, and these readily interconvert especially in aqueous solution. The name \"ribose\" is used in biochemistry and biology to refer to all of these forms, though more specific names for each are used when required.  In its linear form, ribose can be recognised as the pentose sugar with all of its hydroxyl functional groups on the same side in its Fischer projection.  d-Ribose has these hydroxyl groups on the right hand side and is associated with the systematic name (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal, whilst  l-ribose has its hydroxyl groups appear on the left hand side in a Fischer projection.  Cyclisation of ribose occurs via hemiacetal formation due to attack on the aldehyde by the C4' hydroxyl group to produce a furanose form or by the C5' hydroxyl group to produce a pyranose form.  In each case, there are two possible geometric outcomes, named as \u03b1- and \u03b2- and known as anomers, depending on the stereochemistry at the hemiacetal carbon atom (the \"anomeric carbon\").  At room temperature, about 76% of  d-ribose is present in pyranose forms (\u03b1:\u03b2 = 1:2) and 24% in the furanose forms (\u03b1:\u03b2 = 1:3), with only about 0.1% of the linear form present.\nThe ribonucleosides adenosine, cytidine, guanosine, and uridine are all derivatives of \u03b2-d-ribofuranose.  Metabolically important species that include phosphorylated ribose include ADP, ATP, coenzyme A, and NADH.  cAMP and cGMP serve as secondary messengers in some signaling pathways and are also ribose derivatives.  The ribose moiety appears in some pharmaceutical agents, including the antibiotics neomycin and paromomycin.\n\n"}