Isoguanosine

Details

• Internal ID: 489e3b02-5e55-43ab-b832-bd0418d30250
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-2-one
• SMILES (Canonical): C1=NC2=C(NC(=O)N=C2N1C3C(C(C(O3)CO)O)O)N
• SMILES (Isomeric): C1=NC2=C(NC(=O)N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
• InChI: InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
• InChI Key: MIKUYHXYGGJMLM-UUOKFMHZSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 283.24 g/mol
• Exact Mass: 283.09166853 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 2-Hydroxyadenosine
• 1818-71-9
• Isoguanosine
• Isoguanine riboside
• Adenosine, 1,2-dihydro-2-oxo-
• 1,2-Dihydro-2-oxoadenosine
• 6V7FTE1Z1V
• 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-2-one
• 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-2-one
• NSC-12161
• 6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1H-purin-2-one
• 6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-2-one
• RefChem:149394
• Crotonosid
• Adenosine, 2,3-dihydro-2-oxo-
• MFCD04971989
• (2R,3R,4S,5R)-2-(6-Amino-2-hydroxy-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• CHEBI:3927
• 9-(b-D-Ribofuranosyl)isoguanine
• 6-azanyl-9-[(2R,3R,4S,5R)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]-1H-purin-2-one
• Isoguanosine (VAN)
• Isoguanine, 9-beta-D-ribofuranosyl-
• NSC 12161
• Isoguanosine (7CI,8CI)
• CCRIS 8240
• Isoguanine, 9-.beta.-D-ribofuranosyl-
• 9H-Purin-2-ol, 6-amino-9-beta-D-ribofuranosyl-
• H5F
• Isoguanosine;Crotonoside
• 2-Oxoado (isoguanosine)
• UNII-6V7FTE1Z1V
• orb1300272
• SCHEMBL2773634
• SCHEMBL2773640
• SCHEMBL7952864
• CHEMBL1688963
• BDBM82031
• Crotonoside, >=95% (HPLC)
• MIKUYHXYGGJMLM-UUOKFMHZSA-N
• HY-N0071
• 2,3-DIHYDRO-2-OXOADENOSINE
• PDSP1_000998
• PDSP2_000982
• s9275
• AKOS015969770
• CCG-267276
• NR09651
• AC-33996
• AS-59704
• BP-58626
• CAS_1818-71-9
• DB-006158
• CS-0007114
• NS00066984
• C08432
• F12745
• F239124
• Q27106249
• 9H-PURIN-2-OL, 6-AMINO-9-.BETA.-D-RIBOFURANOSYL-(6C
• 6-amino-9-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-3H-purin-2(9H)-one;9-?-D-Ribofuranosylisoguanine
• 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-2H-purin-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8041	80.41%
Caco-2	-	0.9660	96.60%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Nucleus	0.5004	50.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9463	94.63%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9276	92.76%
P-glycoprotein inhibitior	-	0.9209	92.09%
P-glycoprotein substrate	-	0.8336	83.36%
CYP3A4 substrate	-	0.5731	57.31%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.9745	97.45%
CYP2C9 inhibition	-	0.9708	97.08%
CYP2C19 inhibition	-	0.9567	95.67%
CYP2D6 inhibition	-	0.9617	96.17%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9259	92.59%
CYP inhibitory promiscuity	-	0.9882	98.82%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5927	59.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9637	96.37%
Skin irritation	-	0.7483	74.83%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6942	69.42%
Human Ether-a-go-go-Related Gene inhibition	-	0.5986	59.86%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	-	0.5061	50.61%
skin sensitisation	-	0.8469	84.69%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7486	74.86%
Acute Oral Toxicity (c)	III	0.7230	72.30%
Estrogen receptor binding	-	0.5322	53.22%
Androgen receptor binding	+	0.6724	67.24%
Thyroid receptor binding	+	0.5766	57.66%
Glucocorticoid receptor binding	-	0.4774	47.74%
Aromatase binding	+	0.8312	83.12%
PPAR gamma	+	0.7736	77.36%
Honey bee toxicity	-	0.9136	91.36%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.8270	82.70%

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	96.37%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.60%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.77%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.81%	99.23%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	88.19%	80.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.05%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.59%	86.92%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	85.60%	88.84%
CHEMBL3401	O75469	Pregnane X receptor	84.11%	94.73%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	83.70%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.78%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.12%	95.56%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	81.94%	95.48%
CHEMBL2581	P07339	Cathepsin D	81.82%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.56%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.43%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.17%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.16%	94.45%

Plants that contains it

• Croton tiglium

Cross-Links

• PubChem: 65085
• NPASS: NPC164665
• ChEMBL: CHEMBL1688963
• LOTUS: LTS0081028
• wikiData: Q27106249