Basic information
- CAS
73-03-0- Standard SMILES
Nc1ncnc2c1ncn2C1OC(CO)CC1O- InChIKey
OFEZSBMBBKLLBJ-UHFFFAOYSA-N- Molecular formula
- C10H13N5O3
- Average molar mass
- 251.24 g/mol
Overview
3deoxyadenosine has been reported in Cordyceps militaris, Ophiocordyceps sinensis, and Aspergillus nidulans with data available.
Names & identifiers
- Preferred name
- 9-(3-Deoxypentofuranosyl)-9H-purin-6-amine
- IUPAC
- 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
- English name
- Cordycepin
- Molecular formula
- C10H13N5O3
- Molecular weight
- 251.24
Names & synonyms
9-(3-deoxypentofuranosyl)-9h-purin-6-amineRefChem:1074903DTXCID90209707DTXSID008590903-Deoxyadenosine2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-olCHEMBL42814MLS0033894019-(.beta.-D-3'-Deoxyribofuranosyl)adenine.beta.-D-erythro-Pentofuranoside, adenine-9 3-deoxy-9H-Purine, 6-amino-9-(3-deoxy-.beta.-D-ribofuranosyl)-BRD2581
Show more names
Cipargamin3'-Deoxyadenosine3'-DEOXYADENOSINE3'-dAchongcaoduitangAdenine cordyceposideNSC 63984CORDYCEPINNSC 401022Cordycepine
2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol9H-Purin-6-amine, 9-(3-deoxy-.beta.-D-erythro-pentofuranosyl)-BRD-25819H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)-Cordycepin [M+H]+3'-Deoxyadenosine (cordycepin)SCHEMBL20419171SCHEMBL29056333
Database identifiers
- CAS
73-03-0- PubChem CID
- 248010
- ChEMBL
CHEMBL42814
Properties
Computed structural properties
- XLogP
- -1.2
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 307
Physicochemical properties
- Melting point
- 225 · 225-229 °C
- alpha
- 20 · D20 -47°; D27 -42°
- Boiling point
- 394.4 °C · 394.4°C (rough estimate)
- Density
- 1.2938 · 1.2938 (rough estimate)
- refractive index
- 1.761 · 1.7610 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- Soluble in DMSO (up to 25 mg/ml).
- form
- Powder
- pka
- 13 · 13+-.0.60(Predicted)
- color
- White to Off-white
- biological source
- Cordyceps militaris
- λmax
- 260 nm · 260nm(EtOH)(lit.)
- Merck
- 14 · 14,2529
- BRN
- 35194 · 35194
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
- InChIKey
- OFEZSBMBBKLLBJ-BAJZRUMYSA-N
- SMILES
- Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)C[C@H]3O
- CAS DataBase Reference
- 73 · 73-03-0(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- cordycepin
- FDA UNII
- 8 VF4M2J8 · GZ8VF4M2J8
- NCI Drug Dictionary
- cordycepin
- EPA Substance Registry System
- 3 · Adenosine, 3'-deoxy- (73-03-0)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331
- Precautionary statements
- 280 · P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- Xn,T
- Risk Statements
- 40 · 40-36/37/38-25-20/21/22
- Safety Statements
- 22 · 22-36-45-26
- RIDADR
- 2811 · UN 2811
- WGK Germany
- 3 · 3
- RTECS
- 7358610 · AU7358610
- F
- 10 · 10-21
- HazardClass
- 6.1 · 6.1
- HS Code
- 29349990 · 29349990
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
Safety & regulation
Safety data
- F
- 10-21
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- AU7358610
- ridadr
- UN 2811
- hs_code
- 29349990
- risk_code
- 40-36/37/38-25-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,T
- safety_code
- 22-36-45-26
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301+H311+H331
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
- Precautionary statements
- P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Chemistry & industry
Applications
UsesCordycepin is known to have various kinds of effects of improving immune skill, anti-aging, anti-fatigue, anti-cancer, anti-bacterial, anti-virus, lowering blood glucose and lipid and male hormone.
DescriptionCordycepin (73-03-0) is an adenosine analog lacking the hydroxyl at the 3’ position. Inhibits PARP1and polyadenylation2. Displays anti-inflammatory effects1,3and neuroprotective effects by inhibiting Aβ-induced apoptosis in hippocampal neurons4. Induces apoptosis in a variety of cancer cell lines5. Displays antiobesity effects.6Inhibits cell senescence via activation of AMPK.7Maintains stem cell pluripotency and increases iPS cell generation efficiency.8
UsesFirst reported nucleoside antibiotic.
General DescriptionChemical structure: nucleoside
Upstream & downstream products
Downstream products
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Additional notes
DefinitionChEBI: Cordycepin is a 3'-deoxyribonucleoside and a member of adenosines. It has a role as an antimetabolite and a nucleoside antibiotic.
Related reactions
2 records
Compound notes
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