Skip to Content
MilliporeSigma
All Photos(1)

Documents

SMB00287

Sigma-Aldrich

Formycin A

from Streptomyces kaniharaensis, ≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
6742-12-7
Molecular Weight:
267.24
Beilstein/REAXYS Number:
624229
MDL number:
MFCD00036807
UNSPSC Code:
51101500
PubChem Substance ID:
329824924
NACRES:
NA.85

biological source

Streptomyces kaniharaensis

Quality Level

200

assay

≥98% (HPLC)

form

powder

storage condition

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

color

white to off-white

solubility

DMSO: soluble 1 mg/mL
H2O: soluble 3 mg/mL

antibiotic activity spectrum

viruses (Antiretroviral)

mode of action

enzyme | inhibits

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.
Store the product sealed at –20 °C. Under these conditions the product is stable for at least 4 years.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Iturin A from Bacillus subtilis ≥95% (HPLC)

Sigma-Aldrich

I1774

Iturin A from Bacillus subtilis

Surfactin from Bacillus subtilis, ≥98.0% (HPLC)

Sigma-Aldrich

S3523

Surfactin

Fluconazole ≥98% (HPLC), powder

Sigma-Aldrich

F8929

Fluconazole

Tautomerism of the nucleoside antibiotic formycin, as studied by carbon-13 nuclear magnetic resonance.
T R Krugh
Journal of the American Chemical Society, 95(14), 4761-4762 (1973-07-11)
R P Agarwal et al.
The Journal of clinical investigation, 57(4), 1025-1035 (1976-04-01)
Deficiency of erythrocytic and lymphocytic adenosine deaminase (ADA) occurs in some patients with severe combined immunodeficiency disease (SCID). SCID with ADA deficiency is inherited as an autosomal recessive trait. ADA is markedly reduced or undetectable in affected patients (homozygotes), and
C-4? Truncated carbocyclic formycin derivatives
Zhou J, et al.
Tetrahedron, 62(29), 7009-7013 (2006)
Helmut Rosemeyer et al.
Chemistry & biodiversity, 16(4), e1900012-e1900012 (2019-02-19)
Two lipophilic derivatives of formycin A (1) and formycin B (5) carrying an O-2',3'-(ethyl levulinate) ketal group have been prepared. These were base-alkylated at N(1) (for 1) and N(1) and N(6) (for 5) with both isopentenyl and all-trans-farnesyl residues. Upon
A Bzowska et al.
Biochimica et biophysica acta, 1120(3), 239-247 (1992-04-17)
Formycin B (FB), a moderate inhibitor (Ki approximately 100 microM) of mammalian purine nucleoside phosphorylase (PNP), and formycin A (FA), which is totally inactive vs. the mammalian enzyme, are both effective inhibitors of the bacterial (Escherichia coli) enzyme (Ki approximately
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service