2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one

Details

• Internal ID: 2d5d2035-4e02-47bf-952f-b431b7a72dc5
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
• SMILES (Canonical): C1=NC2=C(N1C3C(C(C(O3)CO)O)O)NC(=NC2=O)N
• SMILES (Isomeric): C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=NC2=O)N
• InChI: InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)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: NYHBQMYGNKIUIF-UUOKFMHZSA-N
• Popularity: 53 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): 155.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7925	79.25%
Caco-2	-	0.9693	96.93%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Nucleus	0.3950	39.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9342	93.42%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9428	94.28%
P-glycoprotein inhibitior	-	0.9225	92.25%
P-glycoprotein substrate	-	0.8620	86.20%
CYP3A4 substrate	-	0.5773	57.73%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8779	87.79%
CYP3A4 inhibition	-	0.9767	97.67%
CYP2C9 inhibition	-	0.9565	95.65%
CYP2C19 inhibition	-	0.9524	95.24%
CYP2D6 inhibition	-	0.9636	96.36%
CYP1A2 inhibition	-	0.8071	80.71%
CYP2C8 inhibition	-	0.9456	94.56%
CYP inhibitory promiscuity	-	0.9927	99.27%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4566	45.66%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9660	96.60%
Skin irritation	-	0.7495	74.95%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.5181	51.81%
Human Ether-a-go-go-Related Gene inhibition	-	0.6556	65.56%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.6742	67.42%
skin sensitisation	-	0.8410	84.10%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6992	69.92%
Acute Oral Toxicity (c)	III	0.7202	72.02%
Estrogen receptor binding	-	0.5059	50.59%
Androgen receptor binding	+	0.5204	52.04%
Thyroid receptor binding	+	0.5751	57.51%
Glucocorticoid receptor binding	-	0.5198	51.98%
Aromatase binding	+	0.8598	85.98%
PPAR gamma	+	0.7815	78.15%
Honey bee toxicity	-	0.9103	91.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.8305	83.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	3981.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.99%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.89%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.51%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.71%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.43%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.81%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.99%	91.11%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.76%	80.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.74%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.02%	86.92%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	83.75%	95.48%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	82.80%	100.00%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	81.81%	88.84%
CHEMBL2581	P07339	Cathepsin D	81.07%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	80.94%	97.00%

Plants that contains it

• Abelmoschus manihot
• Allium sativum
• Angelica sinensis
• Arabidopsis thaliana
• Aralidium pinnatifidum
• Arisaema amurense
• Arisaema erubescens
• Arisaema heterophyllum
• Astragalus mongholicus
• Bersama swinnyi
• Blainvillea acmella
• Breynia androgyna
• Carthamus tinctorius
• Cistanche phelypaea
• Dendrobium chrysanthum
• Dendrobium chrysotoxum
• Dendrobium fimbriatum
• Dendrobium loddigesii
• Dendrobium moniliforme
• Dendrobium nobile
• Eschweilera coriacea
• Eucalyptus cladocalyx
• Euphorbia resinifera
• Euryale ferox
• Eurycoma longifolia
• Fritillaria cirrhosa
• Fritillaria delavayi
• Fritillaria monantha
• Fritillaria pallidiflora
• Fritillaria przewalskii
• Fritillaria taipaiensis
• Fritillaria thunbergii
• Fritillaria unibracteata
• Fritillaria verticillata
• Fritillaria walujewii
• Gastrodia elata
• Geigeria schinzii
• Goniothalamus undulatus
• Gymnospermium kiangnanensis
• Helichrysum sutherlandii
• Hemionitis marantae
• Isatis tinctoria
• Isodon rubescens
• Lonicera japonica
• Lophocereus marginatus
• Nemuaron vieillardii
• Ophiopogon japonicus
• Ophryosporus charua
• Oreomecon radicata
• Pachycereus pringlei
• Panax ginseng
• Panax notoginseng
• Peltodon longipes
• Persicaria tinctoria
• Peucedanum japonicum
• Picea laxa
• Pinellia ternata
• Pogostemon cablin
• Prosopis kuntzei
• Pteris leptophylla
• Rehmannia glutinosa
• Rubus idaeus
• Salvadora persica
• Selaginella pulvinata
• Selaginella tamariscina
• Sinocrassula indica
• Solanum lycopersicum
• Stenocereus thurberi
• Typha angustifolia
• Typha orientalis
• Vitex negundo
• Zea mays
• Ziziphus jujuba

Cross-Links

• PubChem: 6802
• NPASS: NPC61198
• ChEMBL: CHEMBL375655
• LOTUS: LTS0044502
• wikiData: Q422462