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Cytosine

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Identification
Molecular formula
C9H13N3O5
CAS number
71-30-7
IUPAC name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
State
State
Cytosine is a solid at room temperature.
Melting point (Celsius)
320.00
Melting point (Kelvin)
593.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
243.22g/mol
Molar mass
143.1300g/mol
Density
1.7000g/cm3
Appearence

Cytosine appears as a white crystalline solid at room temperature.

Comment on solubility

Solubility of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

The solubility of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one (C9H13N3O5) can be described as follows:

  • General Solubility: This compound is expected to have good solubility in polar solvents due to the presence of multiple hydroxyl (–OH) groups.
  • Water Solubility: It is likely soluble in water, as the hydroxyl groups create favorable interactions with water molecules through hydrogen bonding.
  • Solvent Variability: In less polar solvents, solubility may decrease due to reduced ability to form favorable interactions.
  • Biological Relevance: Its solubility profile can significantly affect its biological activity and absorption in pharmaceutical applications.

Overall, the functionality of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one, particularly its hydroxyl groups, plays a critical role in its solubility characteristics. As noted, "In chemistry, solubility is key to understanding the behavior and utility of a compound." Thus, its solubility can influence both its practical applications and theoretical discussions in various chemical contexts.

Interesting facts

Interesting Facts about 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

This compound, often referenced in the realms of medicinal chemistry, showcases a unique structural configuration that incorporates both a pyrimidine and a sugar moiety. Below are some fascinating details:

  • Structure and Functionality: The incorporation of a pyrimidin-2-one structure lends this compound potential as a lead compound in drug design, particularly in targeting nucleic acid interactions.
  • Biological Relevance: Compounds with similar structures are often investigated for their roles as enzyme inhibitors or in modulation of metabolic pathways, making them of great interest in pharmacology.
  • Chirality Matters: The presence of multiple stereocenters enhances the compound's complexity, indicating that the 3D arrangement of atoms significantly influences its biological activity.
  • Natural Occurrence: This compound, or its derivatives, might mimic the natural nucleosides found in biological systems, positioning it potentially for roles in gene synthesis or modulation.
  • Research Potential: Ongoing studies may reveal its applications in treating various diseases, including viral infections and cancer, due to its innovative features.

In conclusion, the intriguing structure of 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one serves as a prime example of how the intersection of organic chemistry and biological science can lead to novel therapeutic discoveries. As scientists continue to explore its properties, they remain hopeful for significant breakthroughs in medicinal applications.

Synonyms
cytarabine
147-94-4
Ara-C
Cytosine arabinoside
Aracytidine
Arabinocytidine
Cytarabinoside
Spongocytidine
Aracytin
Cytosar-U
Depocyt
Udicil
Arabinofuranosylcytosine
Arabitin
Aracytine
Cytarabina
Tarabine
Arafcyt
Erpalfa
Cytosine beta-D-arabinofuranoside
arabinocytosine
Citarabina
Cytarabinum
DepoCyte
1-beta-D-Arabinofuranosylcytosine
Arabinosylcytosine
Cytarabin
Cytosar
Cytosinearabinoside
Depocyt (liposomal)
beta-D-Arabinosylcytosine
Cytosine arabinofuranoside
Alexan
Cytosine beta-D-arabinoside
Cytarabinum [INN-Latin]
Arabinoside C
1beta-D-Arabinosylcytosine
4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Citarabina [INN-Spanish]
Cytosine-1-beta-D-arabinofuranoside
AraC
Cytosine arabinose
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone
1beta-Arabinofuranasylcytosine
Iretin
Cytosine 1-beta-D-arabinofuranoside
1beta-D-Arabinofuranosylcytosine
1-beta-D-Arabinofaranosylcytosine
beta-Arabinosylcytosine
Ara-Cytidine
U 19920A
Beta-cytosine arabinoside
Cytosine-beta-arabinoside
Cytosine-beta-D-arabinofuranoside
cytarabine liposome
CHX 3311
CCRIS 913
U-19,920
1-Arabinofuranosylcytosine
4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one
Arabinofuranosyl Cytidine
Cytosine |A-D-Arabinofuranoside
Cytosine, 1-beta-D-arabinosyl-
1-beta-D-Arabinosylcytosine
HSDB 3049
1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
EINECS 205-705-9
1-(arabinofuranosyl)cytosine
MFCD00066487
Cyclocide
Cytosine, 1-beta-D-arabinofuranosyl-
NSC 287459
UNII-04079A1RDZ
1-beta-arabinofuranosylcytosine
U-19920
DTXSID3022877
CHEBI:28680
AI3-52329
(beta-D-Arabinofuranosyl)cytosine
4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin
04079A1RDZ
2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-
CHEMBL803
NSC-287459
MK 8242
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
C9H13N3O5
DTXCID702877
2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-arabinofuranosyl-
AR3
Cytonal
NCI-C04728
VYXEOS COMPONENT CYTARABINE
1-beta-D-arabinofuranosyl-cytosine
4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine
AC-1075
beta-Ara C
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Cytarabine [USAN:USP:INN:BAN:JAN]
NCGC00093356-03
2(1H)-Pyrimidinone, 4-amino-1-y-D-arabinofuranosyl- [CAS]
Cytarbel
(Arabinofuranosyl)cytosine
Cytarabinum (INN-Latin)
Citarabina (INN-Spanish)
CYTARABINE (MART.)
CYTARABINE [MART.]
CYTARABINE (USP-RS)
CYTARABINE [USP-RS]
Citozar
ara-Cytosine
Cytosine arabinoside (VAN)
Tarabine PFS
CYTARABINE (EP MONOGRAPH)
CYTARABINE (USP IMPURITY)
CYTARABINE [EP MONOGRAPH]
CYTARABINE [USP IMPURITY]
Cytosine-1-beta-arabinofuranoside
CYTARABINE (USP MONOGRAPH)
CYTARABINE [USP MONOGRAPH]
69-74-9
Ara-cell
Cytarabine (USAN:USP:INN:BAN:JAN)
cytarabine liposome injection
Arabinosyl Cytosine
Cytosine, beta-D-arabinoside
CAS-147-94-4
SMR000449317
Depocyt (TN)
Arabinoside, Cytosine
Cytartbine
Arabine
1-.beta.-D-Arabinofuranosylcytosine
Cytarabine; 4-amino-1-beta-d-arabinofuranosylpyrimidin-2(1H)-one
SR-01000075773
NSC287459
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon [Czech]
4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [Czech]
1-(beta-d-arabinofuranosyl)cytosine
1-.beta.-D-arabinofuranosyl-cytosine
4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone
U-19920 A
cytarabine ocphosphate
1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside
Cytarabine (Standard)
beta -arabinosylcytosine
Arabinofuranosylcytosine?
CYTARABINE [MI]
U 19920
CYTARABINE [INN]
CYTARABINE [JAN]
CYTARABINE [HSDB]
CYTARABINE [USAN]
beta -cytosine arabinoside
beta -D-arabinosylcytosine
Cytosine-beta -arabinoside
CYTARABINE [VANDF]
SCHEMBL3140
1beta -D-Arabinosylcytosine
CYTARABINE [WHO-DD]
CYTARABINE [WHO-IP]
BIDD:PXR0139
Lopac0_000316
MLS000758310
MLS001066340
MLS001424023
1-beta-D-Arabinosyl-Cytosine
BIDD:GT0371
CYTARABINE [EMA EPAR]
Cytosine, beta -D-arabinoside
1beta -Arabinofuranasylcytosine
Cytarabine (JP18/USP/INN)
Cytarabine - Bio-X trade mark
GTPL4827
1-ss-D-Arabinofuranosylcytosine
2(1H)-Pyrimidinone, 4-amino-1beta-D-arabinofuranosyl-
CYTARABINE [ORANGE BOOK]
SCHEMBL22591193
SCHEMBL23152019
1beta -D-Arabinofuranosylcytosine
BETA-CYTOSINE, ARABINOSIDE
L01BC01
Cytosine, 1-beta -D-arabinosyl-
1-beta -d-arabinofuranosylcytosine
1-beta-D-arabinofuranosyl cytosine
Cytosine-beta -D-arabinofuranoside
HMS2051K19
HMS2090A18
HMS2230M16
HMS3713N12
1-beta -D-Arabinofaranosylcytosine
CYTARABINE LIPOSOME [VANDF]
CYTARABINUM [WHO-IP LATIN]
BCP02876
Tox21_111203
Tox21_301971
BDBM50087289
CCG-51297
HY-13605R
s1648
AKOS007930145
AKOS015896896
Cytosine, 1-beta -D-arabinofuranosyl-
DB00987
KS-5063
NA05771
NC00070
SDCCGSBI-0050304.P002
NCGC00093356-04
NCGC00093356-05
NCGC00093356-06
NCGC00093356-19
NCGC00142483-02
NCGC00255381-01
1(BETA-D-ARABINOFURANOSYL)CYTOSINE
BA164339
HY-13605
SRI-10828-19
SRI-10828-20
SRI-10828_24
WR-28453
SL-000002
U 19,920A
C2035
NS00005949
SW197450-5
C02961
D00168
EN300-118320
1-BETA-D-ARABINOFURANOSYLCYTOSINE; ARA-C
Q180983
SR-01000721860
SR-01000075773-3
SR-01000075773-5
SR-01000721860-6
U 19,920
1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl
BRD-K33106058-001-07-7
BRD-K33106058-001-16-8
BRD-K33106058-003-20-6
1-BETA-D-ARABINOSYL-4-AMINO-2(1H)PYRIMIDINONE
2(1H)-Pyrimidinone, 4-amino-1beta -D-arabinofuranosyl-
Cytosine -D-arabinofuranoside;Cytosine Arabinoside;Ara-C
Z1511499171
2(1H)-Pyrimidinone, 4-amino-1-beta -D-arabinofuranosyl-
Cytarabine, European Pharmacopoeia (EP) Reference Standard
Cytarabine, United States Pharmacopeia (USP) Reference Standard
Cytosine beta-D-arabinofuranoside, crystalline, >=90% (HPLC)
Cytosine beta-D-arabinofuranoside, Vetec(TM) reagent grade, 90%
Cytarabine, Pharmaceutical Secondary Standard; Certified Reference Material
Cytosine-b-D-arabinofuranoside;4-Amino-1-(b-D-Arabinofuranosyl)-2(1H)pyrimidinone
205-705-9
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
Cytosine -D-arabinofuranoside hydrochloride;Cytosine Arabinoside hydrochloride;Ara-C hydrochloride
Cytosine-b-D-arabinofuranoside;1-(b-D-Arabinofuranosyl)cytosine;4-Amino-1-(b-D-Arabinofuranosyl)-2(1H)pyrimidinone