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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

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
6742-12-7
Molecular Weight:
267.24
Beilstein:
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)

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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

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

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’.

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Jeffrey E Lee et al.
The Journal of biological chemistry, 278(10), 8761-8770 (2002-12-24)
5'-Methylthioadenosine/S-adenosylhomocysteine (MTA/AdoHcy) nucleosidase is a key enzyme in a number of critical biological processes in many microbes. This nucleosidase catalyzes the irreversible hydrolysis of the N(9)-C(1') bond of MTA or AdoHcy to form adenine and the corresponding thioribose. The key
W J Malaisse et al.
Biochemical and molecular medicine, 57(1), 47-63 (1996-02-01)
Formycin A augments insulin release evoked by glucose (5.6 mm or more), this effect not being rapidly reversible. The mechanism responsible for the insulinotropic action of formycin A was investigated in isolated pancreatic islets. It could not be ascribed to
Meng Zhang et al.
Applied and environmental microbiology, 86(2) (2019-11-05)
Formycin A (FOR-A) and pyrazofurin A (PRF-A) are purine-related C-nucleoside antibiotics in which ribose and a pyrazole-derived base are linked by a C-glycosidic bond. However, the logic underlying the biosynthesis of these molecules has remained largely unexplored. Here, we report
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
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