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SMB00287 Sigma-Aldrich

Formycin A

from Streptomyces kaniharaensis, ≥98% (HPLC)

Synonym: 1-C-(7-Amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1,4-anhydro-(1S)-D-Ribitol, 7-Amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidine, 8-Aza-9-deazaadenosine, Formycin, NSC 102811

  • CAS Number 6742-12-7

  • Empirical Formula (Hill Notation) C10H13N5O4

  • Molecular Weight 267.24

  •  Beilstein/REAXYS Number 624229

  •  MDL number MFCD00036807

  •  PubChem Substance ID 329824924

  •  NACRES NA.85

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Mechanism of Action, Antibiotics  A-F, Antiviral,
Quality Level   200
biological source   Streptomyces kaniharaensis
assay   ≥98% (HPLC)
form   powder
color   white to off-white
solubility   DMSO: soluble 1 mg/mL
  H2O: soluble 3 mg/mL
Mode of action   enzyme | inhibits
antibiotic activity spectrum   viruses (Antiretroviral)
storage temp.   −20°C
SMILES string   Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
InChI   1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI key   OIRDTQYFTABQOQ-KQYNXXCUSA-N
Gene Information   human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)

Description

General description

Chemical structure: nucleoside

Formycin A is an adenosine analog, and is cytotoxic in nature. It acts as a substrate for the human enzymes human erythrocytic adenosine deaminase and adenosine kinase.

Biochem/physiol Actions

Formycin A (FA) is a C-nucleoside that inhibits the E.coli enzyme purine nucleoside phosphorylase (PNP). FA was found to upsurge insulin release elevated by glucose, and was also shown to inhibit 5′-Methylthioadenosine/S-adenosylhomocysteine (MTA/AdoHcy) nucleosidase, an enzyme important in the recycling of methionine. Research has shown FA is an antiretroviral agent against HIV-1, targeting reverse transcription.

Formycin A possess antitumor function, along with its antibacterial and antiviral activity.

Packaging

10MG

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
UR0719000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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