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4097-04-5 molecular structure
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pentasodium ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]phosphinate

ChemBase ID: 155104
Molecular Formular: C20H24N10Na5O22P5
Molecular Mass: 1026.276015
Monoisotopic Mass: 1025.92431701
SMILES and InChIs

SMILES:
c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O)O)O)N.[Na+].[Na+].[Na+].[Na+].[Na+]
Canonical SMILES:
O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2ncnc3N)[O-])[O-])[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Na+].[Na+].[Na+].[Na+].[Na+]
InChI:
InChI=1S/C20H29N10O22P5.5Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30;;;;;/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26);;;;;/q;5*+1/p-5/t7-,8-,11-,12-,13-,14-,19-,20-;;;;;/m1...../s1
InChIKey:
NNMFUJJMJIYTSP-CSMIRWGRSA-I

Cite this record

CBID:155104 http://www.chembase.cn/molecule-155104.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
pentasodium ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]phosphinate
IUPAC Traditional name
pentasodium Ap5A
Synonyms
A(5′)P5(5′)A
Diadenosine pentaphosphate pentasodium salt
P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt
CAS Number
4097-04-5
EC Number
223-852-7
MDL Number
MFCD00077718
Beilstein Number
4949216
PubChem SID
24893808
162249242
PubChem CID
16219241

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 16219241 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 0.4076155  H Acceptors 24 
H Donor LogD (pH = 5.5) -16.54053 
LogD (pH = 7.4) -16.970062  Log P -10.989128 
Molar Refractivity 171.3682 cm3 Polarizability 70.863716 Å3
Polar Surface Area 494.65 Å2 Rotatable Bonds 16 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL expand Show data source
H2O: soluble50 mg/mL, clear, slightly yellow expand Show data source
Apperance
white to white with yellow cast powder expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥96.0% (HPLC) expand Show data source
Linear Formula
C20H29N10O22P5 · 5 Na expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - D4022 external link
Biochem/physiol Actions
A diadenosine polyphosphate stored in secretory granules of thrombocytes, chromaffin and neuronal cells. After release into the extracellular space, it affects a variety of biological activities in a wide range of target tissues. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.1
Sigma Aldrich - 31588 external link
Biochem/physiol Actions
A diadenosine polyphosphate stored in secretory granules of thrombocytes, chromaffin and neuronal cells. After release into the extracellular space, it affects a variety of biological activities in a wide range of target tissues. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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