Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-05-16 21:32:43 UTC
Update Date2025-10-07 16:08:19 UTC
Metabolite IDMMDBc0053718
Metabolite Identification
Common NameStreptidine 6-phosphate
DescriptionStreptidine 6-phosphate is a phosphoaminosugar and a key intermediate in the biosynthesis of streptomycin, belonging to the chemical class of nucleoside phosphates. Its chemical structure features a streptidine moiety linked to a phosphate group, which plays a crucial role in various enzymatic pathways. In the biosynthetic pathway of streptomycin, streptidine 6-phosphate is involved in the linkage to dihydrostreptose, as evidenced by the isolation of streptomycin-nonproducing mutants that are deficient in the biosynthesis of this moiety (PMID:3922295 ). Additionally, the accumulation of streptidine 6-phosphate has been shown to impair aminotransferase activity in certain mutants (PMID:3922295 ). The enzymatic conversion of streptidine 6-phosphate into dihydrostreptomycin 6-phosphate is facilitated by specific enzymatic reactions, highlighting its role as a substrate in these biochemical processes (PMID:6157663 ). Moreover, streptidine 6-phosphate serves as an acceptor in the synthesis of O-alpha-L-dihydrostreptose-streptidine 6-phosphate, further emphasizing its importance in the metabolic pathways of antibiotic production (PMID:6768553 ).
Structure
Synonyms
ValueSource
D-Streptamine, N,n'-bis(aminoiminomethyl)-, 6-(dihydrogen phosphate)ChEBI
Streptidine-6-phosphateChEBI
D-Streptamine, N,n'-bis(aminoiminomethyl)-, 6-(dihydrogen phosphoric acid)Generator
Streptidine 6-phosphoric acidGenerator
Streptidine-6-phosphoric acidGenerator
Molecular FormulaC8H19N6O7P
Average Mass342.249
Monoisotopic Mass342.105283974
IUPAC Name{[(1S,2R,3S,4S,5R,6S)-2,4-dicarbamimidamido-3,5,6-trihydroxycyclohexyl]oxy}phosphonic acid
Traditional Namestreptidine-6-phosphate
CAS Registry NumberNot Available
SMILES
NC(=N)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](OP(O)(O)=O)[C@H](NC(N)=N)[C@H]1O
InChI Identifier
InChI=1S/C8H19N6O7P/c9-7(10)13-1-3(15)2(14-8(11)12)6(5(17)4(1)16)21-22(18,19)20/h1-6,15-17H,(H4,9,10,13)(H4,11,12,14)(H2,18,19,20)/t1-,2+,3-,4+,5-,6-/m0/s1
InChI KeyUUUGVWGQJIFFRM-FUHDGFEASA-N