4-Amino-1-pentofuranosyl-2(1H)-pyrimidinone

Details

• Internal ID: 31617430-343b-4d21-b2c5-525e035d5351
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleosides
• IUPAC Name: 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• InChI: InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)
• InChI Key: UHDGCWIWMRVCDJ-UHFFFAOYSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃N₃O₅
• Molecular Weight: 243.22 g/mol
• Exact Mass: 243.08552052 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.56
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• cytidine-1'-13C
• .beta.-Arabinosylcytosine
• .beta.-Cytosine arabinoside
• .beta.-D-Arabinosylcytosine
• Cytosine-.beta.-arabinoside
• Arabinofuranosylcytosine
• Cytarabin
• 1.beta.-D-Arabinosylcytosine
• [2'-13C]CYTIDINE
• [5',5''-2H2]cytidine
• MLS003389283
• 688007-26-3
• Cytosine, .beta.-D-arabinoside
• 1.beta.-Arabinofuranasylcytosine
• Arabinosylcytosine
• Cytosine arabinose
• 1.beta.-D-Arabinofuranosylcytosine
• 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Cytosine, 1-.beta.-D-arabinosyl-
• Cytosine-.beta.-D-arabinofuranoside
• 1-.beta.-D-Arabinofaranosylcytosine
• Cylocide
• NSC 63878
• Cytidine-5,6-d2
• Cytosine, 1-.beta.-D-arabinofuranosyl-
• 1-Arabinofuranosylcytosine
• 478511-21-6
• Iretin
• 1-.beta.-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
• Cytosine-beta-D-arabinofuranoside
• NCI-C04728
• MLS002702869
• 4-Amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
• SMR001549941
• 1.beta.-Ribofuranosylcytosine
• 4-amino-1-pentofuranosylpyrimidin-2(1H)-one
• 40632-25-5
• 1.beta.-D-Ribofuranosylcytosine
• 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine
• Cytosine beta-D-arabinofuranoside;Cytosine Arabinoside;Ara-C
• Cytosine beta-D-riboside;Cytosine-1-beta-D-ribofuranoside
• 1-.beta.-D-Arabinofuranosylcytosine
• MFCD00066487
• NSC287459
• .beta.-D-Ribofuranoside, cytosine-1
• CYTARABINE, Cytarabine (Cytosine 1-b-D-arabinofuranoside), CYTIDINE
• Cytosine, 1-.beta.-D-ribofuranosyl-
• AC-1075
• 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one
• 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Cytosine beta-D-arabinofuranoside hydrochloride;Cytosine Arabinoside hydrochloride;Ara-C hydrochloride
• U-19920 A
• U 19920
• AC 1075
• CHEMBL78
• 4-Amino-1.beta.-D-ribofuranosyl-2(1H)-pyrimidinone
• ChemDiv1_027335
• MolMap_000003
• 2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-ribofuranosyl-
• Oprea1_593929
• Oprea1_858801
• SCHEMBL149563
• Cytosine .beta.-D-arabinoside
• HMS664K11
• DTXSID80859078
• 1-.beta.-Arabinofuranosylcytosine
• 1-.beta.-D-Ribofuranosylcytosine
• UHDGCWIWMRVCDJ-UHFFFAOYSA-N
• HMS3371G12
• HMS3393K19
• HMS3428O03
• HMS3655P13
• CHX-3311
• NSC20258
• NSC249004
• AKOS001590380
• AKOS017259253
• Cytosine-1-.beta.-D-arabinofuranoside
• NSC-249004
• SMP2_000209
• NCGC00015258-02
• NCGC00015258-03
• NCGC00015258-04
• NCGC00015258-05
• NCGC00094638-01
• NCGC00094638-02
• NCGC00094638-03
• NCGC00094638-04
• AS-12090
• NCI60_012951
• SY004943
• SY005417
• FT-0624314
• FT-0624315
• FT-0774114
• WLN: T6NVNJ DZ A-BT5OTJ CQ DQ E1Q
• AB01273973-01
• EN300-1073140
• L001298
• SR-01000597029
• SR-01000597029-1
• 2(1H)-Pyrimidinone, 4-amino-1.beta.-D-ribofuranosyl-
• 4-Amino-1-.beta.-D-arabinofuranosyl-2(1H)-pyrimidinon
• 4-Amino-1-.beta.-d-arabinofuranosyl-2(1H)-pyrimidinone
• 2(1H)-Pyrimidinone, 4-amino-1.beta.-D-arabinofuranosyl-
• 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5214	52.14%
Caco-2	-	0.9072	90.72%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Nucleus	0.4886	48.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9461	94.61%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9797	97.97%
P-glycoprotein inhibitior	-	0.9526	95.26%
P-glycoprotein substrate	-	0.9737	97.37%
CYP3A4 substrate	-	0.6285	62.85%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	-	0.9609	96.09%
CYP2C9 inhibition	-	0.9638	96.38%
CYP2C19 inhibition	-	0.9489	94.89%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	-	0.9543	95.43%
CYP2C8 inhibition	-	0.9860	98.60%
CYP inhibitory promiscuity	-	0.9810	98.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.4707	47.07%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9761	97.61%
Skin irritation	-	0.7802	78.02%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7018	70.18%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	+	0.9502	95.02%
skin sensitisation	-	0.8566	85.66%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.4497	44.97%
Acute Oral Toxicity (c)	III	0.7926	79.26%
Estrogen receptor binding	-	0.5448	54.48%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5416	54.16%
Glucocorticoid receptor binding	+	0.6838	68.38%
Aromatase binding	+	0.5341	53.41%
PPAR gamma	+	0.7112	71.12%
Honey bee toxicity	-	0.9394	93.94%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.9006	90.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5023	Q00987	p53-binding protein Mdm-2	20 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	39.8 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	73.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	96.07%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.60%	96.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	92.18%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	89.22%	98.46%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.92%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.35%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.83%	86.33%

Plants that contains it

• Capsicum annuum
• Castanopsis fissa
• Morinda citrifolia

Cross-Links

• PubChem: 596
• LOTUS: LTS0050374
• wikiData: Q77514687