Xanthosine-5'-monophosphate

Details

• Internal ID: e46a7d9f-d440-4116-93c6-49e9754bef65
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside monophosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(2,6-dioxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• SMILES (Canonical): C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)O)O)O)NC(=O)NC2=O
• SMILES (Isomeric): C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)NC(=O)NC2=O
• InChI: InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1
• InChI Key: DCTLYFZHFGENCW-UUOKFMHZSA-N
• Popularity: 333 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃N₄O₉P
• Molecular Weight: 364.21 g/mol
• Exact Mass: 364.04201500 g/mol
• Topological Polar Surface Area (TPSA): 193.00 Ų
• XlogP: -4.00
• Atomic LogP (AlogP): -2.86
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• xanthosine monophosphate
• 523-98-8
• xanthosine-5'-monophosphate
• Xanthosine 5'-phosphate
• Xanthylic acid
• (9-D-ribosylxanthine)-5'-phosphate
• XMP
• [(2R,3S,4R,5R)-5-(2,6-dioxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CHEBI:15652
• xanthosine-5'-P
• 9-[(2~{R},3~{R},4~{S},5~{R})-3,4-bis(oxidanyl)-5-[[tris(oxidanyl)-$l^{5}-phosphanyl]oxymethyl]oxolan-2-yl]-2-oxidanyl-1~{H}-purin-6-one
• Y29K672ETF
• XANTHOSINE 5'-MONOPHOSPHATE
• 1lol
• 1pkx
• (((2R,3S,4R,5R)-5-(2,6-DIOXO-2,3,6,9-TETRAHYDRO-1H-PURIN-9-YL)-3,4-DIHYDROXYOXOLAN-2-YL)METHOXY)PHOSPHONIC ACID
• {[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• xanthosine-5-phosphate
• 1m9n
• xanthosine-5'-phosphate
• Ammonium ((2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate
• 5'-xanthonylate monophosphate
• SCHEMBL188739
• CHEMBL1206243
• DTXSID20966674
• PD006971
• C00655
• EN300-7430402
• A848951
• Q3132209
• Q50362394
• XANTHOSINE, MONO(DIHYDROGEN PHOSPHATE) (ESTER)
• ((2S,3R,4S,5S)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methyl dihydrogen phosphate
• HYJ

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6480	64.80%
Caco-2	-	0.9396	93.96%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4559	45.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9322	93.22%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8965	89.65%
P-glycoprotein inhibitior	-	0.8305	83.05%
P-glycoprotein substrate	-	0.8731	87.31%
CYP3A4 substrate	+	0.5306	53.06%
CYP2C9 substrate	-	0.7947	79.47%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	-	0.9573	95.73%
CYP2C9 inhibition	-	0.9385	93.85%
CYP2C19 inhibition	-	0.9246	92.46%
CYP2D6 inhibition	-	0.8934	89.34%
CYP1A2 inhibition	-	0.8481	84.81%
CYP2C8 inhibition	-	0.8726	87.26%
CYP inhibitory promiscuity	-	0.9700	97.00%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6157	61.57%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9495	94.95%
Skin irritation	-	0.7644	76.44%
Skin corrosion	-	0.9287	92.87%
Ames mutagenesis	-	0.7491	74.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7745	77.45%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.5476	54.76%
skin sensitisation	-	0.8436	84.36%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7530	75.30%
Acute Oral Toxicity (c)	III	0.7116	71.16%
Estrogen receptor binding	+	0.6066	60.66%
Androgen receptor binding	-	0.4862	48.62%
Thyroid receptor binding	-	0.5210	52.10%
Glucocorticoid receptor binding	-	0.5661	56.61%
Aromatase binding	+	0.7999	79.99%
PPAR gamma	+	0.5454	54.54%
Honey bee toxicity	-	0.7707	77.07%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.4568	45.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	96.02%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	95.09%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.50%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.37%	99.23%
CHEMBL5957	P21589	5'-nucleotidase	89.33%	97.78%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	87.76%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.33%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.08%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.84%	94.45%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	82.13%	96.47%
CHEMBL226	P30542	Adenosine A1 receptor	82.08%	95.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.36%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.33%	95.56%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 73323
• LOTUS: LTS0107814
• wikiData: Q50362394