Showing Metabocard for 2-deoxy-D-ribose 5-phosphate (BASm0004380)

Common Name2-deoxy-d-ribose 5-phosphate
DescriptionDeoxyribose 5-phosphate is a a metabolite in the pentose phosphate pathway. It can be generated from D-glyceraldehdye-3 phosphate via the enzyme 2-Deoxyribose 5-phosphate aldolase (DERA). Alternately Deoxyribose 5-phosphate can be converted to D-glyceraldehyde-3 phosphate that can then feed into the pentose phosphate pathway. Deoxyribose 5-phosphate can also be generated from 2-Deoxy-D-ribose via the enzyme Ribokinase (EC 2.7.1.15). It has been shown in a number of organisms that deoxynucleosides or deoxyriboses cause the induction of aldolases (such as DERA) involved in their catabolism, leading to the utilisation of the pentose moiety as carbon and energy source.
Structure
Molecular FormulaC5H11O7P
Average Mass214.11040
Monoisotopic Mass214.02424
IUPAC Name{[(2R,3S,5R)-3,5-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,5r)-3,5-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number102916-66-5
SMILESO=P([O-])([O-])OC[C@H]1OC(O)C[C@@H]1O
InChI IdentifierInChI=1S/C5H11O7P/c6-3-1-5(7)12-4(3)2-11-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5+/m0/s1
InChI KeyKKZFLSZAWCYPOC-VPENINKCSA-N
CHEBI IDCHEBI:62877
HMDB IDHMDB0001031
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
StateSolid
Water Solubility3.75e+01 g/l
logP-2.14
logS-0.76
pKa (Strongest Acidic)1.23
pKa (Strongest Basic)-3.26
Hydrogen Acceptor Count6
Hydrogen Donor Count4
Polar Surface Area116.45 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity39.32 m³·mol⁻¹
Polarizability17.46

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