Aristeromycin

Details

• Internal ID: c2fc14d9-4b78-4fc6-b7b7-e66e71ff0e05
• Taxonomy: Nucleosides, nucleotides, and analogues > Nucleoside and nucleotide analogues > Cyclopentyl nucleosides > 1,3-substituted cyclopentyl nucleosides > 1,3-substituted cyclopentyl purine nucleosides
• IUPAC Name: (1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• InChI: InChI=1S/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1
• InChI Key: UGRNVLGKAGREKS-GCXDCGAKSA-N
• Popularity: 170 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₅N₅O₃
• Molecular Weight: 265.27 g/mol
• Exact Mass: 265.11748936 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.32
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 19186-33-5
• Cycloadenosine
• (1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• RefChem:114037
• (1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CHEMBL49935
• (1R,2S,3R,5R)-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
• 1,2-Cyclopentanediol, 5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)-, (1S,2R,3R,5R)-
• NSC 103526
• NSC103526
• SCHEMBL692209
• (-)-.beta.-D-Aristeromycin
• .beta.-D-Carbocyclic adenosine
• orb1710391
• SCHEMBL29695815
• CHEBI:209498
• UGRNVLGKAGREKS-GCXDCGAKSA-N
• GLXC-22191
• AVS-12219
• BDBM50088426
• MFCD00078836
• AKOS030616274
• AT33705
• NC29204
• 1,2-Cyclopentanediol, 3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)-, (1R,2S,3R,5R)-
• 13190-75-5
• DA-50693
• MS-23749
• HY-112639
• CS-0058742
• 9-(2,3-Dihydroxy-4-[hydroxymethyl]cyclopentyl)adenine;Carbocyclic adenosine
• Rel-(1R,2S,3R,5R)-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
• (+/-)-(1R*,2S*,3R*,5R*)-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
• 7CY

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9163	91.63%
Caco-2	-	0.9057	90.57%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Nucleus	0.5977	59.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9671	96.71%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9328	93.28%
P-glycoprotein inhibitior	-	0.9486	94.86%
P-glycoprotein substrate	-	0.6660	66.60%
CYP3A4 substrate	-	0.6322	63.22%
CYP2C9 substrate	-	0.8135	81.35%
CYP2D6 substrate	-	0.8388	83.88%
CYP3A4 inhibition	-	0.9028	90.28%
CYP2C9 inhibition	-	0.9373	93.73%
CYP2C19 inhibition	-	0.9198	91.98%
CYP2D6 inhibition	-	0.9131	91.31%
CYP1A2 inhibition	-	0.9033	90.33%
CYP2C8 inhibition	-	0.8697	86.97%
CYP inhibitory promiscuity	-	0.9319	93.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5906	59.06%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9660	96.60%
Skin irritation	-	0.7560	75.60%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6003	60.03%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.6296	62.96%
skin sensitisation	-	0.8564	85.64%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7077	70.77%
Acute Oral Toxicity (c)	III	0.6393	63.93%
Estrogen receptor binding	-	0.6801	68.01%
Androgen receptor binding	+	0.6579	65.79%
Thyroid receptor binding	+	0.6001	60.01%
Glucocorticoid receptor binding	-	0.5720	57.20%
Aromatase binding	+	0.7146	71.46%
PPAR gamma	+	0.5375	53.75%
Honey bee toxicity	-	0.9389	93.89%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.8836	88.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL255	P29275	Adenosine A2b receptor	47300 nM	Ki	PMID: 10841798
CHEMBL2664	P23526	Adenosylhomocysteinase	4850 nM; 303 nM; 303 nM	IC50; IC50; IC50	PMID: 18295495; PMID: 24813734; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.24%	96.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	96.10%	100.00%
CHEMBL3589	P55263	Adenosine kinase	93.81%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.13%	97.09%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	87.20%	95.48%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	84.17%	90.17%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.75%	98.46%
CHEMBL1978	P11511	Cytochrome P450 19A1	82.98%	91.76%

Plants that contains it

• Gypsophila vaccaria

Cross-Links

• PubChem: 65269
• NPASS: NPC93365
• ChEMBL: CHEMBL49935
• LOTUS: LTS0184400
• wikiData: Q104402216