Np mrd loader

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Record Information
Version2.0
Created at2020-11-23 18:26:24 UTC
Updated at2021-08-12 19:51:48 UTC
NP-MRD IDNP0002665
Secondary Accession NumbersNone
Natural Product Identification
Common NamedADP
Provided ByBMRBBMRB logo
DescriptionDADP, also known as 2'-dADP, belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. DADP exists in all living organisms, ranging from bacteria to humans. In humans, dADP is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. DADP is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. dADP is found in Apis cerana and Daphnia pulex. dADP was first documented in 1969 (PMID: 11947151). Based on a literature review a small amount of articles have been published on dADP (PMID: 1545776) (PMID: 23721485) (PMID: 5316336).
Structure
Thumb
Synonyms
ValueSource
2'-Deoxyadenosine 5'-diphosphateChEBI
2'-DEOXYADENOSINE-5'-diphosphATEChEBI
Deoxyadenosine diphosphateChEBI
2'-Deoxyadenosine 5'-diphosphoric acidGenerator
2'-DEOXYADENOSINE-5'-diphosphoric acidGenerator
Deoxyadenosine diphosphoric acidGenerator
2'-Deoxyadenosine 5'-(trihydrogen diphosphate)HMDB
2'-Deoxyadenosine 5'-pyrophosphateHMDB
2'-Deoxyadenosine diphosphateHMDB
2'-dADPHMDB
2’-deoxyadenosine 5’-(trihydrogen diphosphate)HMDB
2’-deoxyadenosine 5’-diphosphateHMDB
2’-deoxyadenosine 5’-pyrophosphateHMDB
2’-deoxyadenosine diphosphateHMDB
2’-dADPHMDB
Deoxyadenosine 5'-diphosphateHMDB
Deoxyadenosine 5’-diphosphateHMDB
2’-deoxyadenosine-5’-diphosphateHMDB
2’-deoxyadenosine-5’-diphosphoric acidHMDB
dADPHMDB
Chemical FormulaC10H15N5O9P2
Average Mass411.2017 Da
Monoisotopic Mass411.03450 Da
IUPAC Name[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional NamedADP
CAS Registry NumberNot Available
SMILES
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1
InChI Identifier
InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
InChI KeyDAEAPNUQQAICNR-RRKCRQDMSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achyrocline flaccidaKNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Andromeda polifoliaKNApSAcK Database
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Cheilanthes kaulfussiiKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eremophila alternifoliaKNApSAcK Database
Eremophila racemosissimaKNApSAcK Database
Gallus gallusFooDB
Helichrysum aureumKNApSAcK Database
Helichrysum graveolenKNApSAcK Database
Helichrysum picardiiKNApSAcK Database
Heliotropium filifoliumKNApSAcK Database
Heliotropium huascoenseKNApSAcK Database
Heliotropium huascuenseKNApSAcK Database
Heliotropium megalanthumKNApSAcK Database
Heliotropium pycnophyllumKNApSAcK Database
Heliotropium sinuatumKNApSAcK Database
Heliotropium stenophyllumKNApSAcK Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lychnophora markgraviiKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Nothofagus spp.KNApSAcK Database
Notholaena candidaKNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Ozothamnus spp.KNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Populus nigraKNApSAcK Database
Pseudognaphalium cheiranthifoliumKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Woodsia scopulinaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside diphosphates
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-3.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area212.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.43 m³·mol⁻¹ChemAxon
Polarizability33.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0001508
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022662
KNApSAcK IDC00004534
Chemspider ID164196
KEGG Compound IDC00206
BioCyc IDCPD-11700
BiGG IDNot Available
Wikipedia LinkDeoxyadenosine_diphosphate
METLIN IDNot Available
PubChem Compound188966
PDB IDNot Available
ChEBI ID16174
Good Scents IDNot Available
References
General References
  1. Kaufmann G, Littauer UZ: Deoxyadenosine diphosphate as substrate for polynucleotide phosphorylase from Escherichia coli. FEBS Lett. 1969 Jul;4(2):79-83. doi: 10.1016/0014-5793(69)80201-2. [PubMed:11947151 ]
  2. Schwanstecher C, Dickel C, Panten U: Cytosolic nucleotides enhance the tolbutamide sensitivity of the ATP-dependent K+ channel in mouse pancreatic B cells by their combined actions at inhibitory and stimulatory receptors. Mol Pharmacol. 1992 Mar;41(3):480-6. [PubMed:1545776 ]
  3. Das U, Wang LK, Smith P, Shuman S: Structural and biochemical analysis of the phosphate donor specificity of the polynucleotide kinase component of the bacterial pnkp*hen1 RNA repair system. Biochemistry. 2013 Jul 9;52(27):4734-43. doi: 10.1021/bi400412x. Epub 2013 Jun 26. [PubMed:23721485 ]
  4. Chou JY, Singer MF: Deoxyadenosine diphosphate as a substrate and inhibitor of polynucleotide phosphorylase of Micrococcus luteus. I. Deoxyadenosine diphosphate as a substrate for polymerization and the exchange reaction with inorganic 32 P. J Biol Chem. 1971 Dec 25;246(24):7486-96. [PubMed:5316336 ]