Record Information
Version1.0
Created at2020-04-17 19:14:16 UTC
Updated at2020-11-18 16:39:26 UTC
CannabisDB IDCDB005149
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAdenosine 3',5'-diphosphate
DescriptionAdenosine 3',5'-diphosphate, also known as 3-phosphoadenosine 5-phosphate or 3'-phosphoadenylate, belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. Adenosine 3',5'-diphosphate is a strong basic compound (based on its pKa). Adenosine 3',5'-diphosphate exists in all living species, ranging from bacteria to humans. Outside of the human body, Adenosine 3',5'-diphosphate has been detected, but not quantified in, several different foods, such as scarlet beans, tronchuda cabbages, horseradish tree, shallots, and lindens. This could make adenosine 3',5'-diphosphate a potential biomarker for the consumption of these foods. An adenosine bisphosphate having two monophosphate groups at the 3'- and 5'-positions. Adenosine 3',5'-diphosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
3'-PhosphoadenylateChEBI
Adenosine 3',5'-bisphosphateChEBI
PAPChEBI
Phosphoadenosine phosphateChEBI
3'-Phosphoadenylic acidGenerator
Adenosine 3',5'-bisphosphoric acidGenerator
Phosphoadenosine phosphoric acidGenerator
Adenosine 3',5'-diphosphoric acidGenerator
3'-Phosphoryl-AMPHMDB
3,5-ADPHMDB
3,5-DiphosphoadenosineHMDB
3-Phosphoadenosine 5-phosphateHMDB
5-(Dihydrogen phosphate) 3-adenylateHMDB
5-(Dihydrogen phosphate)3'-adenylic acidHMDB
Adenosine 3,5-bisHMDB
Adenosine 3,5-bisphosphateHMDB
Adenosine 3'-phosphate-5'-phosphate, disodium saltHMDB
3'-Phosphoadenosine 5'-phosphateHMDB
Adenosine 3'-phosphate-5'-phosphate, monosodium saltHMDB
3',5'-ADPHMDB
Adenosine 3'-phosphate-5'-phosphateHMDB
Chemical FormulaC10H15N5O10P2
Average Molecular Weight427.2
Monoisotopic Molecular Weight427.0294
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
Traditional Nameadenosine 3',5'-bisphosphate
CAS Registry Number1053-73-2
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1
InChI KeyWHTCPDAXWFLDIH-KQYNXXCUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside 3',5'-bisphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Phosphoric acid ester
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • Alkyl phosphate
  • Imidazole
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility614.5 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-4.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.7ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.94 m³·mol⁻¹ChemAxon
Polarizability34.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAdenosine 3',5'-diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9332100000-c2cf1343058e5c460684Spectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9141400000-8e8cf251eecd6d39cf02Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-000i-0913100000-4559e980fc823f06cda1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-000i-0910000000-164b37f4075a5627b64dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-000i-1900000000-0f28c9a19c771609202dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0902300000-77268ef9fe8672f81e9fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-6986eb10675f363acf42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-493254661a51349997bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7801900000-b4b0af4deca129a6a12cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9800000000-4a1ffcf05d9938fe121eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-fb4a5bf16d0e5bcaa1e0Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Carbohydrate sulfotransferase 11CHST1112qQ9NPF2 details
Carbohydrate sulfotransferase 3CHST310q22.1Q7LGC8 details
Carbohydrate sulfotransferase 13CHST133q21.3Q8NET6 details
Carbohydrate sulfotransferase 12CHST127p22Q9NRB3 details
Galactosylceramide sulfotransferaseGAL3ST122q12.2Q99999 details
Heparan sulfate glucosamine 3-O-sulfotransferase 3B1HS3ST3B117p12Q9Y662 details
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1HS3ST3A117p12Q9Y663 details
Sulfotransferase 1A1SULT1A116p12.1P50225 details
3'(2'),5'-bisphosphate nucleotidase 1BPNT11q41O95861 details
Heparan sulfate glucosamine 3-O-sulfotransferase 1HS3ST14p16O14792 details
Estrogen sulfotransferaseSULT1E14q13.1P49888 details
Bile salt sulfotransferaseSULT2A119q13.3Q06520 details
Carbohydrate sulfotransferase 1CHST111p11.2O43916 details
Heparan sulfate glucosamine 3-O-sulfotransferase 4HS3ST416p11.2Q9Y661 details
Sulfotransferase 1A2SULT1A216p12.1P50226 details
Heparan sulfate glucosamine 3-O-sulfotransferase 5HS3ST56q21Q8IZT8 details
Heparan sulfate glucosamine 3-O-sulfotransferase 2HS3ST216p12Q9Y278 details
Protein-tyrosine sulfotransferase 2TPST222q12.1O60704 details
Sulfotransferase family cytosolic 2B member 1SULT2B119q13.3O00204 details
Sulfotransferase 1A3/1A4SULT1A316p11.2P50224 details
Carbohydrate sulfotransferase 7CHST7Xp11.23Q9NS84 details
Carbohydrate sulfotransferase 14CHST1415q15.1Q8NCH0 details
Heparan-sulfate 6-O-sulfotransferase 1HS6ST12q21O60243 details
Heparan-sulfate 6-O-sulfotransferase 2HS6ST2Xq26.2Q96MM7 details
Heparan-sulfate 6-O-sulfotransferase 3HS6ST313q32.1Q8IZP7 details
Carbohydrate sulfotransferase 15CHST1510q26Q7LFX5 details
Inositol monophosphatase 3IMPAD18q12.1Q9NX62 details
Tyrosylprotein sulfotransferase 1TPST17q11.21A4D2M0 details
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPT11q22Q9NRN7 details
Heparan sulfate glucosamine 3-O-sulfotransferase 6HS3ST6Q96QI5 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1NDST15q33.1P52848 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 2NDST210q22P52849 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 3NDST34q26O95803 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 4NDST44q26Q9H3R1 details
Sulfotransferase 1C3SULT1C32q12.3Q6IMI6 details
Sulfotransferase 6B1SULT6B1Q6IMI4 details
Protein-tyrosine sulfotransferase 1TPST17q11.21O60507 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Inositol monophosphatase 3IMPAD18q12.1Q9NX62 details
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPT11q22Q9NRN7 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Carbohydrate sulfotransferase 11CHST1112qQ9NPF2 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1NDST15q33.1P52848 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000061
DrugBank IDDB01812
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030650
KNApSAcK IDC00019352
Chemspider ID140102
KEGG Compound IDC00054
BioCyc ID3-5-ADP
BiGG ID33684
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound159296
PDB IDNot Available
ChEBI ID17985
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 47 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues in desulfated dermatan sulfate. Preferentially sulfates in GlcA->GalNAc unit than in IdoA->GalNAc unit. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:
CHST11
Uniprot ID:
Q9NPF2
Molecular weight:
41002.97
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues of keratan sulfate, another glycosaminoglycan, and the Gal residues in sialyl N-acetyllactosamine (sialyl LacNAc) oligosaccharides. May play a role in the maintenance of naive T-lymphocytes in the spleen.
Gene Name:
CHST3
Uniprot ID:
Q7LGC8
Molecular weight:
54705.5
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Transfers sulfate to the C4 hydroxyl of beta1,4-linked GalNAc that is substituted with a beta-linked glucuronic acid at the C-3 hydroxyl. No activity toward dermatan.
Gene Name:
CHST13
Uniprot ID:
Q8NET6
Molecular weight:
38919.34
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin and desulfated dermatan sulfate. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Activity toward partially desulfated dermatan sulfate is however lower. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:
CHST12
Uniprot ID:
Q9NRB3
Molecular weight:
48413.945
General function:
Involved in galactosylceramide sulfotransferase activity
Specific function:
Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of galactosylceramide sulfate (sulfatide), a major lipid component of the myelin sheath and of monogalactosylalkylacylglycerol sulfate (seminolipid), present in spermatocytes (By similarity). Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro).
Gene Name:
GAL3ST1
Uniprot ID:
Q99999
Molecular weight:
48763.63
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
Gene Name:
HS3ST3B1
Uniprot ID:
Q9Y662
Molecular weight:
43323.605
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
Gene Name:
HS3ST3A1
Uniprot ID:
Q9Y663
Molecular weight:
44899.155
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:
SULT1A1
Uniprot ID:
P50225
Molecular weight:
34165.13

Only showing the first 10 proteins. There are 47 proteins in total.