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3768-14-7 molecular structure
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[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid

ChemBase ID: 133324
Molecular Formular: C11H17N5O9P2
Molecular Mass: 425.228302
Monoisotopic Mass: 425.05015041
SMILES and InChIs

SMILES:
c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(CP(=O)(O)O)O)O)O)N
Canonical SMILES:
O[C@@H]1[C@@H](COP(=O)(CP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
InChI:
InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1
InChIKey:
OLCWZBFDIYXLAA-IOSLPCCCSA-N

Cite this record

CBID:133324 http://www.chembase.cn/molecule-133324.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid
IUPAC Traditional name
α,β-methylene adp
Synonyms
α,β-Methyleneadenosine 5′-diphosphate
ADP[α,β-CH2]
AMP-CP
Adenosine 5′-(α,β-methylene)diphosphate
CAS Number
3768-14-7
EC Number
223-194-0
MDL Number
MFCD00042991
Beilstein Number
633678
PubChem SID
162227601
24896872
PubChem CID
92199

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 92199 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 0.98112744  H Acceptors 12 
H Donor LogD (pH = 5.5) -8.182416 
LogD (pH = 7.4) -8.16192  Log P -5.8846297 
Molar Refractivity 87.2951 cm3 Polarizability 34.85279 Å3
Polar Surface Area 223.37 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Safety Statements
22-24/25 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
≥99.0% (HPLC) expand Show data source
Empirical Formula (Hill Notation)
C11H17N5O9P2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - M3763 external link
Application
Adenosine 5′-(α,β-methylene)diphosphate (AMP-CP) is a CD73 inhibitor and is used to study adenosinergic signaling regulation via CD73/ecto-5′-nucleotidase.
Reconstitution
soluble in water up to Approx. 50 mg/ml with heating
Sigma Aldrich - 01920 external link
Other Notes
Powerful inhibitor of 5′-nucleotidase from rat heart membranes1; Useful tool in kinetic studies with 5′-nucleotidase2

REFERENCES

REFERENCES

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PATENTS

PATENTS

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