Basic information
- Standard SMILES
CCCC(=O)Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1OC(=O)CCC- InChIKey
CJGYSWNGNKCJSB-YVLZZHOMSA-N- Molecular formula
- C18H24N5O8P
- Average molar mass
- 469.4 g/mol
- Monoisotopic mass
- 469.13624974
Names & identifiers
- Preferred name
- Bucladesine
- IUPAC
- [(4aR,6R,7R,7aR)-6-[6-(butanoylamino)purin-9-yl]-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
- English name
- Bucladesine
- Molecular formula
- C18H24N5O8P
- Molecular weight
- 469.39
Names & synonyms
bucladesineDibutyryl cAMP362-74-3Dibutyryl cyclic AMPdBcAMPActosinCyclic AMP dibutyrateBucladesinaDibutyryl-3',5'-AMPDibutyryl 3',5'-cyclic AMPBucladesinum3',5'-Cyclic AMP dibutyrate
Show more names
BucladesinN-(9-beta-D-RibofuraDibutyryl cyclic 3',5'-AMPCalciuM DibutyacyladenosineBucladesine (Dibutyryl-cAMP)Butyryladenosine Cyclophosphate
Dibutyryladenosine cyclic monophosphateDibutyryl cyclic 3',5'-adenylic acidDibutyryl adenosine 3',5'-monophosphateDibutyryl adenosine 3',5'-cyclic phosphateDTXSID1040459Dibutyryl cyclic adenosine monophosphateDibutyryladenosine 3',5'-cyclic monophosphateDibutyryl cyclic adenosine 3',5'-monophosphate
Database identifiers
- CAS
362-74-3- PubChem CID
- 9687
- DTXSID
DTXSID1040459- ChEMBL
CHEMBL485980- ChEBI
CHEBI:50095- UNII
- 63X7MBT2LQ
- EC Number
- 206-649-8
- Nikkaji
- J33.134A
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 164 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 8
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 759
Experimental & physicochemical properties
Collision Cross Section
215.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
210.36 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；214.52 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；214.45 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Density
- 1.72 · 1.72±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO; Methano
- pka
- 0.82 · 0.82±0.60(Predicted)
- form
- Solid
- color
- White
- FDA UNII
- 63 X7MBT2LQ · 63X7MBT2LQ
- ATC code
- 1 CE04 · C01CE04
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H320-H335
- Precautionary statements
- 264 · P264-P270-P301+P312-P330
Safety & regulation
Hazard information
Other Safety Information
IMAP assessments - Adenosine, N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphate) 2'-butanoate: Environment tier I assessment；IMAP assessments - Adenosine, N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphate) 2'-butanoate: Human health tier I assessment
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H320-H335
- Precautionary statements
- P264-P270-P301+P312-P330
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system；C01 - Cardiac therapy；C01C - Cardiac stimulants excl. cardiac glycosides；C01CE - Phosphodiesterase inhibitors；C01CE04 - Bucladesine
QC - Cardiovascular system；QC01 - Cardiac therapy；QC01C - Cardiac stimulants excl. cardiac glycosides；QC01CE - Phosphodiesterase inhibitors；QC01CE04 - Bucladesine
Applications
DescriptionBucladesine is a cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed)
UsesBucladesine is a cell permeable cAMP analog. The compound is used in a wide variety of research applications because it mimics cAMP and can induce normal physiological responses when added to cells in experimental conditions. cAMP is only able to elicit minimal responses in these situations. The neurite outgrowth instigated by bucladesine in cell cultures has been shown to be enhanced by nardosinone.
Suppliers50 total
Hangzhou Meiya Pharmaceutical Co Ltd+86-021-33686691 +86-18001850931 · [email protected]
郑州汇聚化工有限公司0371-53399770 18037166334 · [email protected]
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Watson Biotechnology Co.,Ltd+86-18186686046 · [email protected]
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Additional notes
DefinitionChEBI: Bucladesine is a 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP. It has a role as an agonist, a vasodilator agent and a cardiotonic drug. It is a butyrate ester, a 3',5'-cyclic purine nucleotide and a member of butanamides. It is functionally related to a 3',5'-cyclic AMP.
Related reactions
2 records
Linked notes
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