1-β-D-Arabinofuranosyluracil

Names

[ Name ]:
1-β-D-Arabinofuranosyluracil

[Synonym ]:
Uracil 1-β-D-Arabinofuranoside
1-Pentofuranosyl-2,4(1H,3H)-pyrimidinedione
4-Hydroxy-1-pentofuranosylpyrimidin-2(1H)-one
1-pentofuranosylpyrimidine-2,4(1H,3H)-dione
Uracil arabinoside
Spongouridine
1-β-D-Arabinofuranosyluracil
1-[3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidindion
1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H- pyrimidine-2,4-dione
1-.β.-D-Arabinofuranosyluracil
2,4(1H,3H)-Pyrimidinedione, 1-pentofuranosyl-
MFCD00065998
1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione
EINECS 221-386-9
2(1H)-pyrimidinone, 4-hydroxy-1-pentofuranosyl-
1-[3,4-Dihydroxy-5-(hydroxyméthyl)tétrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione
1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Biological Activity

[Description]:

1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[References]

[1]. Bertin MJ, et al. Spongosine production by a Vibrio harveyi strain associated with the sponge Tectitethya crypta. J Nat Prod. 2015 Mar 27;78(3):493-9.

[2]. Müller WE, et al. Metabolism of 1-beta-D-arabinofuranosyluracil in mouse L5178Y cells. Cancer Res. 1979 Mar;39(3):1102-7.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Melting Point ]:
220-222ºC

[ Molecular Formula ]:
C₉H₁₂N₂O₆

[ Molecular Weight ]:
244.201

[ Exact Mass ]:
244.069534

[ PSA ]:
124.78000

[ LogP ]:
-1.61

[ Index of Refraction ]:
1.643

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YQ8818000

CHEMICAL NAME :: Uracil, 1-beta-D-arabinofuranosyl-

CAS REGISTRY NUMBER :: 3083-77-0

BEILSTEIN REFERENCE NO. :: 0028749

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C9-H12-N2-O6

MOLECULAR WEIGHT :: 244.23

WISWESSER LINE NOTATION :: T6NVMVJ A- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 90 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 2820 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 42,3957,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
22-24/25-36-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YQ8818000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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