Tubercidin

Details

• Internal ID: 723ed6d2-7a23-4a2e-90b9-7a272d40a95e
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrrolopyrimidine nucleosides and nucleotides
• IUPAC Name: (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• SMILES (Canonical): C1=CN(C2=NC=NC(=C21)N)C3C(C(C(O3)CO)O)O
• SMILES (Isomeric): C1=CN(C2=NC=NC(=C21)N)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• InChI: InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
• InChI Key: HDZZVAMISRMYHH-KCGFPETGSA-N
• Popularity: 1,077 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄N₄O₄
• Molecular Weight: 266.25 g/mol
• Exact Mass: 266.10150494 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.38
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 7-Deazaadenosine
• 69-33-0
• Sparsomycin A
• Tubercidine
• U-10071
• M351LCX45Y
• 7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7-beta-D-ribofuranosyl-
• 4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine
• 7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 7-beta-D-ribofuranosyl-
• 7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7beta-D-ribofuranosyl-
• CHEBI:48267
• DTXSID701018946
• NSC-56408
• 7-beta-D-Ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• U 10071
• (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• (2R,3R,4S,5R)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Deazaadenosine
• 7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• NSC56408
• 4-Amino-7beta-D-ribofuranosyl-7H-pyrrolo(2, 3-d)pyrimidine
• 4-amino-7beta-D-ribofuranosyl-7H-pyrrolo[2, 3-d]pyrimidine
• 7-(beta-D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine
• 7H-Pyrrolo[2,3-d]pyrimidine, 4-amino-7-beta-D-ribofuranosyl-
• 7-BETA-D-RIBOFURANOSYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-AMINE
• 7 Deazaadenosine
• (2R,3R,4S,5R)-2-(4-aminopyrrolo(2,3-d)pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo(2,3-d)pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• RefChem:192438
• 4-Amino-7 beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine
• DTXCID201476959
• 4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2, 3-d)pyrimidine
• 200-703-4
• MFCD00056012
• 4-Amino-7-(b-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• sparsamycin A
• CHEMBL267099
• Antibiotic XK 101-1
• SKI 26996
• 4-Amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• Tubercidin Trifluoroacetate
• (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 4-Amino-7-(|A-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• U10071
• 2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
• (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• EINECS 200-703-4
• BRN 0038498
• UNII-M351LCX45Y
• Tubercidin?
• AI3-52353
• 1pr5
• 4-Amino-7-(beta-D-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine
• 4-Amino-7beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine
• 7-beta-D-Ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-4-amine
• 7beta-D-Ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-4-amine
• TUBERCIDIN [MI]
• cid_6245
• SCHEMBL8259
• 4-26-00-01117 (Beilstein Handbook Reference)
• MLS001074702
• BIDD:GT0715
• 7-Deazaadenosine (Tubercidin)
• GTPL4755
• orb1300150
• SCHEMBL29388871
• 7-beta-CD-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidin-4-amine
• 7-beta-D-ribofuranosyl-7H-pyrrolo-(2,3-d)pyrimidin-4-amine
• GLXC-04100
• HMS2269L05
• EX-A1062
• BDBM50000298
• AKOS024464517
• CS-5578
• DB03172
• EBC-463059
• ND06290
• NCGC00163638-01
• AC-32279
• BS-17423
• SMR000471894
• SY066715
• HY-100126
• NS00011706
• F463458
• SR-01000765501
• Tubercidin, from Streptomyces tubercidicus, ~95%
• SR-01000765501-3
• Q27089034
• 4-Amino-7-(?-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 7-.BETA.-D-RIBOFURANOSYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-AMINE
• Tubercidin;4-Amino-7-b-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine;7-Deaza-D-adenosine
• ''2-(4-AMINO-PYRROLO[2,3-D]PYRIMIDIN-7-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL
• (2R,3R,4S,5R)-2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
• 2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (Tubercidin)
• 2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol(tubercidin)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5681	56.81%
Caco-2	-	0.8651	86.51%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Nucleus	0.3952	39.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9536	95.36%
OATP1B3 inhibitior	+	0.9507	95.07%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9624	96.24%
P-glycoprotein inhibitior	-	0.9185	91.85%
P-glycoprotein substrate	-	0.9091	90.91%
CYP3A4 substrate	-	0.5857	58.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.9559	95.59%
CYP2C9 inhibition	-	0.9479	94.79%
CYP2C19 inhibition	-	0.9397	93.97%
CYP2D6 inhibition	-	0.9743	97.43%
CYP1A2 inhibition	-	0.9688	96.88%
CYP2C8 inhibition	-	0.7882	78.82%
CYP inhibitory promiscuity	-	0.9623	96.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5207	52.07%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9331	93.31%
Skin irritation	-	0.7716	77.16%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.7337	73.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5121	51.21%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5988	59.88%
skin sensitisation	-	0.8661	86.61%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7666	76.66%
Acute Oral Toxicity (c)	I	0.8430	84.30%
Estrogen receptor binding	-	0.5313	53.13%
Androgen receptor binding	+	0.5590	55.90%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6076	60.76%
Aromatase binding	+	0.7652	76.52%
PPAR gamma	+	0.6614	66.14%
Honey bee toxicity	-	0.9152	91.52%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.9124	91.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1781868	Q53EL6	Programmed cell death protein 4	880 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137261	O14744	PRMT5/MEP50 complex	98.65%	100.00%
CHEMBL3589	P55263	Adenosine kinase	98.09%	98.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.36%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.49%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.15%	97.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.97%	93.10%
CHEMBL1795116	O14744	Protein arginine N-methyltransferase 5	80.67%	97.50%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.48%	98.46%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	80.30%	95.48%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6245
• LOTUS: LTS0265017
• wikiData: Q27089034