1-beta-D-Arabinofuranosyl-5-methyl-2,4(1H,3H)-pyrimidinedione

Details

• Internal ID: c53f74f0-6067-40dc-a245-91c873ead7e9
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleosides
• IUPAC Name: 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7+,9-/m1/s1
• InChI Key: DWRXFEITVBNRMK-JAGXHNFQSA-N
• Popularity: 115 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄N₂O₆
• Molecular Weight: 258.23 g/mol
• Exact Mass: 258.08518617 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -2.54
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 605-23-2
• Arabinosylthymine
• 1-beta-D-Arabinofuranosylthymine
• Thymine arabinoside
• Spongothymidin
• ara-T
• NS9U4BEG7Y
• CHEMBL103283
• CHEBI:80699
• 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 2,4(1H,3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-methyl-
• 1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• EINECS 210-083-7
• UNII-NS9U4BEG7Y
• NSC 68929
• BRN 0090166
• Thymine-beta-D -arabinofuranoside
• 1-.beta.-D-Arabinofuranosylthymine
• NSC-68929
• Thymine, 1-.beta.-D-arabinofuranosyl-
• 1-(beta-D-arabinofuranosyl)thymine
• Thymine, 1-beta-D-arabinofuranosyl-
• MFCD00065474
• 1-beta-D-Arabinofuranosyl-5-methyl-(1H,3H)-pyrimidine-2,4-dione
• Thymine, 1-beta-D-arabinofuranosyl- (VAN)
• 4-24-00-01308 (Beilstein Handbook Reference)
• 5-METHYLARABINOSYLURACIL
• SCHEMBL1619684
• DTXSID201194189
• 2,4(1H,3H)-Pyrimidinedione, 1-beta-D-arabinofuranosyl-5-methyl-
• BDBM50132291
• Thymine 1- beta -D-arabinofuranoside
• 1-beta-D-Arabinofuranosylthymine, araT
• Thymine, 1-.beta.-D-arabinofuranoside
• 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
• 1-.BETA.-D ARABINOFURANOSYLTHYMINE
• F89223
• Q27149733
• 1--D-Arabinofuranosyl-5-methyl-2,4(1H,3H)-pyrimidinedione
• 1-beta-D-Arabinofuranosyl-5-methyl-2,4(1H,3H)-pyrimidinedione
• 1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 1-((2R,3S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9216	92.16%
Caco-2	-	0.9486	94.86%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4487	44.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9356	93.56%
P-glycoprotein inhibitior	-	0.9116	91.16%
P-glycoprotein substrate	-	0.9672	96.72%
CYP3A4 substrate	-	0.5695	56.95%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.9600	96.00%
CYP2C9 inhibition	-	0.9567	95.67%
CYP2C19 inhibition	-	0.9390	93.90%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.9376	93.76%
CYP2C8 inhibition	-	0.9801	98.01%
CYP inhibitory promiscuity	-	0.9712	97.12%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4913	49.13%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9411	94.11%
Skin irritation	-	0.8162	81.62%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7026	70.26%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	+	0.7394	73.94%
skin sensitisation	-	0.8977	89.77%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6008	60.08%
Acute Oral Toxicity (c)	III	0.6657	66.57%
Estrogen receptor binding	-	0.6467	64.67%
Androgen receptor binding	+	0.5958	59.58%
Thyroid receptor binding	-	0.5789	57.89%
Glucocorticoid receptor binding	-	0.4641	46.41%
Aromatase binding	-	0.6930	69.30%
PPAR gamma	+	0.6473	64.73%
Honey bee toxicity	-	0.9483	94.83%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.8248	82.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.80%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.32%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.18%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	84.90%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.23%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.77%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.43%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.24%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.01%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 65049
• LOTUS: LTS0106198
• wikiData: Q27149733