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Basic information
- CAS
69-33-0- Standard SMILES
Nc1ncnc2c1ccn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
HDZZVAMISRMYHH-KCGFPETGSA-N- Molecular formula
- C11H14N4O4
- Average molar mass
- 266.25 g/mol
- Monoisotopic mass
- 266.10150493
Overview
Tubercidin is an N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. It has a role as an antimetabolite, an antineoplastic agent and a bacterial metabolite. It is a ribonucleoside, a N-glycosylpyrrolopyrimidine and an antibiotic antifungal agent.
Names & identifiers
- Preferred name
- Tubercidin
- IUPAC
- (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- English name
- TUBERCIDIN
- Molecular formula
- C11H14N4O4
- Molecular weight
- 266.25
Names & synonyms
tubercidin7-Deazaadenosine69-33-0Sparsomycin ATubercidineU-10071M351LCX45Y7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7-beta-D-ribofuranosyl-7-beta-D-Ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 7-beta-D-ribofuranosyl-7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7beta-D-ribofuranosyl-
Show more names
(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolb120121CS-2599nsc56408ski26996Aids0519837-Deaza-Ar
CHEBI:48267DTXSID701018946NSC-564087-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineU 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-diolDeazaadenosine
Database identifiers
Properties
Computed structural propertiesFilling in
- XLogP
- -1.3
- Topological polar surface area
- 127 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 334
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 247 · 247-248 °C (decomp)(Solv: water (7732-18-5))
- alpha
- 17 · D17 -67° (50% acetic acid)
- Boiling point
- 409.46 °C · 409.46°C (rough estimate)
- Density
- 1.2896 · 1.2896 (rough estimate)
- refractive index
- 1.834 · 1.8340 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Soluble in DMSO
- form
- powder
- pka
- 12.44 · 12.44±0.70(Predicted)
- color
- off-white
- Merck
- 13 · 13,9875
- BRN
- 38498 · 38498
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 70 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information7H-Pyrrolo2,3-dpyrimidin-4-amine, 7-.beta.-D-ribofuranosyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- F
- 10
- wgk
- 3
- rtecs
- UY8870000
- ridadr
- UN 3462 6.1/PG 2
- hs_code
- 29419090
- Toxicity
- LD50 i.v. in mice: 45 mg/kg (Anzai)
- risk_code
- 28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 36/37/39-45
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H300
- Precautionary statements
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Antimetabolites that are useful in cancer chemotherapy.
Applications
UsesTubercidin is a nucleoside metabolite first isolated from Streptomyces tubericidus. Tubercidin, like other nucleosides, is a broad spectrum, potent chemotherapeutic agent active against viruses, bacteria, fungi, protozoans and tumours. Tubercidin acts at a diverse range of sites, such as RNA processing, nucleic acid and protein synthesis, and acts as a nucleoside mimic of adenosine.
Upstream & downstream products
Downstream products
Suppliers100 total
韶远科技(上海)有限公司4000665055 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Related reactions
6 records
Compound notes
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