Basic information
- CAS
73-03-0- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)C[C@H]1O- InChIKey
OFEZSBMBBKLLBJ-BAJZRUMYSA-N- Molecular formula
- C10H13N5O3
- Average molar mass
- 251.24 g/mol
- Monoisotopic mass
- 251.10183928
Overview
Cordycepin is a member of adenosines and a 3'-deoxyribonucleoside. It has a role as a nucleoside antibiotic and an antimetabolite.
Names & identifiers
- Preferred name
- Cordycepin
- IUPAC
- (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
- English name
- Cordycepin
- Molecular formula
- C10H13N5O3
- Molecular weight
- 251.24
Names & synonyms
Cordycepin3'-Deoxyadenosine73-03-0Cordycepine9-CordyceposidoadenineADENOSINE, 3'-DEOXY-9-(beta-D-3'-Deoxyribofuranosyl)adenineGZ8VF4M2J8NSC-63984DTXSID1041007NSC-401022beta-D-erythro-Pentofuranoside, adenine-9 3-deoxy-
Show more names
Cipargamin3'-dAchongcaoduitangAdenine cordyceposideNSC 63984NSC 401022
(2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-olCHEBI:290149H-Purin-6-amine, 9-(3-deoxy-beta-D-erythro-pentofuranosyl)-(2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-olNSC627047cordycepeneKordicepin3-dAdenosine
Database identifiers
- CAS
73-03-0- PubChem CID
- 6303
- DTXSID
DTXSID1041007- ChEMBL
CHEMBL305686- ChEBI
CHEBI:29014- UNII
- GZ8VF4M2J8
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
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
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.)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (95.3%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationAdenosine, 3'-deoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 3 (95.3%)
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
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.
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
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
Related reactions
1 records
Compound notes
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