2'-Deoxyadenosine

Details

• Internal ID: 345d441a-ac47-4cd7-8abd-b30769522f67
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides > Purine 2-deoxyribonucleosides
• IUPAC Name: (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• SMILES (Canonical): C1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O
• SMILES (Isomeric): C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O
• InChI: InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
• InChI Key: OLXZPDWKRNYJJZ-RRKCRQDMSA-N
• Popularity: 2,927 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃N₅O₃
• Molecular Weight: 251.24 g/mol
• Exact Mass: 251.10183929 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.95
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• deoxyadenosine
• 958-09-8
• Desoxyadenosine
• Adenyldeoxyriboside
• Adenine deoxyribonucleoside
• Adenine deoxyribose
• (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
• ADENOSINE, 2'-DEOXY-
• 2-Deoxyadenosine
• Adenine deoxy nucleoside
• 2'-Deoxyformycin A
• CCRIS 1782
• NSC 141848
• CHEBI:17256
• AI3-52383
• Adenosine, 2'-deoxy,
• EINECS 213-488-7
• NSC 83258
• NSC 143510
• beta-D-erythro-Pentofuranoside, adenine-9 2-deoxy-
• BRN 0091015
• UNII-P582C98ULC
• (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• 9H-Purin-6-amine, 9-(2-deoxy-beta-D-ribofuranosyl)-
• P582C98ULC
• 9H-Purin-6-amine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-
• beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-
• (2R,3S,5R)-5-(6-Aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine
• 2'-dA
• NSC-141848
• desoxyadenosin
• 4-26-00-03589 (Beilstein Handbook Reference)
• 9-(2-deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine
• 9-(2-Deoxy-|A-D-threo-pentofuranosyl)-9H-purin-6-amine
• 2''-Deoxyadenosine
• MFCD00005754
• (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
• (2r,3s,5r)-5-(6-Amino-9h-Purin-9-Yl)-Tetrahydro-2-(Hydroxymethyl)furan-3-Ol
• (R)-1-C-(7-Amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-2-deoxy-D-erythro-pentitol
• 3D1
• 40627-14-3
• 2'-deoxy-d-adenosine
• 5-(6-AMINO-PURIN-9-YL)-2-HYDROXYMETHYL-TETRAHYDRO-FURAN-3-OL
• NSC-83258
• NSC-143510
• 2-deoxy-adenosine
• DNA nucleoside A
• 2''''-Deoxyadenosine
• 9-(2-Deoxy-.beta.-D-erythro-pentofuranosyl)adenine
• D0E0OJ
• D0KA1G
• 2-Deoxyadenosine monohydrate
• SCHEMBL19877
• .beta.-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-
• CHEMBL449329
• GTPL5109
• ACon0_001347
• DTXSID10883624
• 2'-DEOXYADENOSINE [INCI]
• OLXZPDWKRNYJJZ-RRKCRQDMSA-N
• 7005-15-4
• AMY31025
• BCP11997
• BDBM50453912
• AKOS015896793
• CS-W021069
• HY-W040329
• 2'-Deoxyadenosine monohydrate, >=99%
• NCGC00161970-01
• 2'-DEOXYADENOSINE [USP IMPURITY]
• AS-14314
• 2 inverted exclamation marka-Deoxyadenosine
• HY-154058
• CS-0674964
• D0046
• 9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine
• adenine-9 2-deoxy-b-D-erythro-Pentofuranoside
• Adenosine, 2'-deoxy- (6CI,7CI,8CI,9CI)
• C00559
• EN300-108104
• 9-(2-deoxy-b-D-ribofuranosyl)-9H-Purin-6-amine
• Adenine-9 2-deoxy-beta-D-erythro-Pentofuranoside
• Q422457
• adenine-9 2-deoxy-beta-delta-erythro-Pentofuranoside
• 9-(2'-Deoxy-.beta.-D-erythro-pentofuranosyl)adenine
• 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine
• 9-(2-deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-amine
• Z1416201984
• 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranose
• 9-(2-deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine
• 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranose
• 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-amine
• D2DF2A54-B4A8-4727-A05C-3D1123687898
• 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranose
• 9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-amine
• 2'-Deoxyadenosine monohydrate, powder, BioReagent, suitable for cell culture
• 663188-78-1
• 96893-70-8
• D-erythro-Pentitol, 1-C-(7-amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-2-deoxy-, (R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9773	97.73%
Caco-2	-	0.9324	93.24%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Nucleus	0.5664	56.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9571	95.71%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9523	95.23%
P-glycoprotein inhibitior	-	0.9450	94.50%
P-glycoprotein substrate	-	0.8849	88.49%
CYP3A4 substrate	-	0.5984	59.84%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.8432	84.32%
CYP3A4 inhibition	-	0.9431	94.31%
CYP2C9 inhibition	-	0.9463	94.63%
CYP2C19 inhibition	-	0.9327	93.27%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	-	0.9490	94.90%
CYP2C8 inhibition	-	0.8078	80.78%
CYP inhibitory promiscuity	-	0.9215	92.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4592	45.92%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.7784	77.84%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6231	62.31%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.5411	54.11%
skin sensitisation	-	0.8817	88.17%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6976	69.76%
Acute Oral Toxicity (c)	III	0.6540	65.40%
Estrogen receptor binding	-	0.5659	56.59%
Androgen receptor binding	+	0.6548	65.48%
Thyroid receptor binding	+	0.7430	74.30%
Glucocorticoid receptor binding	-	0.5310	53.10%
Aromatase binding	+	0.6080	60.80%
PPAR gamma	+	0.6474	64.74%
Honey bee toxicity	-	0.8686	86.86%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	-	0.8247	82.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	501.2 nM	Potency	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	98.46%	96.09%
CHEMBL3589	P55263	Adenosine kinase	94.58%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.99%	97.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	92.01%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	91.60%	98.46%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	91.44%	80.33%
CHEMBL4040	P28482	MAP kinase ERK2	90.26%	83.82%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	89.24%	95.48%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.24%	94.45%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	87.31%	96.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.85%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.73%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.34%	94.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.52%	91.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.84%	91.11%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.24%	97.53%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.30%	89.00%

Plants that contains it

• Anoectochilus koshunensis
• Euryale ferox
• Foeniculum vulgare
• Fritillaria cirrhosa
• Fritillaria delavayi
• Fritillaria przewalskii
• Fritillaria taipaiensis
• Fritillaria unibracteata
• Fritillaria verticillata
• Linum usitatissimum
• Ziziphus jujuba

Cross-Links

• PubChem: 13730
• NPASS: NPC209525
• ChEMBL: CHEMBL449329
• LOTUS: LTS0010529
• wikiData: Q422457