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1874-54-0

1874-54-0 structure
1874-54-0 structure
  • Name: Psicofuranine
  • Chemical Name: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol
  • CAS Number: 1874-54-0
  • Molecular Formula: C11H15N5O5
  • Molecular Weight: 297.26700
  • Catalog: Signaling Pathways Anti-infection Bacterial
  • Create Date: 2016-09-05 20:33:29
  • Modify Date: 2025-08-22 02:25:56
  • Psicofuramine a nucleoside antibiotic and has the inhibition of xanthosine 5'-phosphate aminase. Psicofuranine also specifically inhibits GMP synthase, and interrupts parasite growth. Psicofuranine exhibits a dose-dependent inhibition of P. falciparum growth[1][2].
Name (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol
Synonyms Adenine,9beta-D-psicofuranosyl
6-Amino-9-D-psicofuranosylpurine
Psicofuranosyladenine
Angustmycin C
psicofuranine
angustmicine C
Description Psicofuramine a nucleoside antibiotic and has the inhibition of xanthosine 5'-phosphate aminase. Psicofuranine also specifically inhibits GMP synthase, and interrupts parasite growth. Psicofuranine exhibits a dose-dependent inhibition of P. falciparum growth[1][2].
Related Catalog
Target

Xanthosine 5'-phosphate aminase[2] P. falciparum[1] E. coli[1]

In Vitro Psicofuranine specifically inhibits bacterial GMP synthase as demonstrated by isolation of Psicofuranine-resistant Escherichia coli mutants with mutations in the gene encoding GMP synthase and inhibition of bacterial growth. Psicofuranine exhibits a dose-dependent inhibition of P. falciparum growth with an IC50 of 0.3 mM. The Psicofuranine inhibitory concentration is similar to that of E. coli[1].
References

[1]. cConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32.

[2]. UDAKA S, et al. INHIBITION OF PARENTAL AND MUTANT XANTHOSINE 5'-PHOSPHATE AMINASES BY PSICOFURANINE. J Biol Chem. 1963 Aug;238:2797-803.
Density 2.02g/cm3
Boiling Point 720.1ºC at 760 mmHg
Molecular Formula C11H15N5O5
Molecular Weight 297.26700
Flash Point 389.3ºC
Exact Mass 297.10700
PSA 159.77000
Vapour Pressure 9.24E-22mmHg at 25°C
Index of Refraction 1.855

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU7100000
CHEMICAL NAME :
Adenine, 9-beta-D-psicofuranosyl-
CAS REGISTRY NUMBER :
1874-54-0
BEILSTEIN REFERENCE NO. :
0095142
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C11-H15-N5-O5
MOLECULAR WEIGHT :
297.31
WISWESSER LINE NOTATION :
T56 BN DN FN HNJ IZ D- BT5OTJ B1Q CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10 gm/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 9,675,1959
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
13 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,842,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1695 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
UPJOH* "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." (Kalamazoo, MI 49001) Volume(issue)/page/year: 2(6),-,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,842,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
UPJOH* "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." (Kalamazoo, MI 49001) Volume(issue)/page/year: 2(6),-,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
9800 mg/kg/28D-I
TOXIC EFFECTS :
Liver - other changes Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 9,675,1959 *** REVIEWS *** TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973
138348-93-3 structure

138348-93-3

~90%

1874-54-0 structure

1874-54-0

Literature: Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584
93417-25-5 structure

93417-25-5

~50%

1874-54-0 structure

1874-54-0

Literature: Grouiller; Chattopadhyaya 1984 , vol. 38, # 5 B p. 367 - 373
138348-91-1 structure

138348-91-1

~74%

1874-54-0 structure

1874-54-0

Literature: Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584
138348-88-6 structure

138348-88-6

~%

1874-54-0 structure

1874-54-0

Literature: Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584
18055-47-5 structure

18055-47-5

~%

1874-54-0 structure

1874-54-0

Literature: Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584
87-42-3 structure

87-42-3

~%

1874-54-0 structure

1874-54-0

Literature: Grouiller; Chattopadhyaya 1984 , vol. 38, # 5 B p. 367 - 373
13019-85-7 structure

13019-85-7

~%

1874-54-0 structure

1874-54-0

Literature: Grouiller; Chattopadhyaya 1984 , vol. 38, # 5 B p. 367 - 373
Precursor  3

DownStream  0

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