Showing Compound Card for Adenosine monophosphate (CDB004790)

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Record Information
Version1.0
Created at2020-04-17 18:37:02 UTC
Updated at2020-12-07 19:10:56 UTC
CannabisDB IDCDB004790
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAdenosine monophosphate
DescriptionAdenosine monophosphate, also known as adenylic acid or 5'-AMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenosine monophosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenosine monophosphate is a strong basic compound (based on its pKa). Adenosine monophosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine monophosphate is involved in the metabolic disorder called the canavan disease pathway. Outside of the human body, Adenosine monophosphate is found, on average, in the highest concentration within beers. Adenosine monophosphate has also been detected, but not quantified in, several different foods, such as spinachs, cowpea, parsley, arctic blackberries, and kumquats. This could make adenosine monophosphate a potential biomarker for the consumption of these foods. A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase. Adenosine monophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC10H14N5O7P
Average Molecular Weight347.22
Monoisotopic Molecular Weight347.0631
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Nameadenylate
CAS Registry Number61-19-8
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
InChI KeyUDMBCSSLTHHNCD-KQYNXXCUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Monosaccharide
  • Pyrimidine
  • Imidolactam
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point195 °CNot Available
Boiling Point798.5 °CWikipedia
Water Solubility10 mg/mL at 20 °CBEILSTEIN
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.1ALOGPS
logP-4.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.07 m³·mol⁻¹ChemAxon
Polarizability29.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Very long-chain acyl-CoA synthetaseSLC27A215q21.2O14975 details
Transient receptor potential cation channel subfamily M member 2TRPM221q22.3O94759 details
Bile acyl-CoA synthetaseSLC27A519q13.43Q9Y2P5 details
Acyl-CoA synthetase family member 4AASDH4q12Q4L235 details
Metal Bindings
Receptors
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Ubiquitin-conjugating enzyme E2 D1UBE2D110q21.1P51668 details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8APDE8A15q25.3O60658 details
Ubiquitin-conjugating enzyme E2 D2UBE2D25q31.2P62837 details
Ubiquitin-conjugating enzyme E2 L3UBE2L322q11.21P68036 details
Ubiquitin-conjugating enzyme E2 D3UBE2D34q24P61077 details
cGMP-dependent 3',5'-cyclic phosphodiesterasePDE2A11q13.4O00408 details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8BPDE8B5q13.3O95263 details
SUMO-conjugating enzyme UBC9UBE2I16p13.3P63279 details
Ubiquitin-conjugating enzyme E2 NUBE2N12q22P61088 details
DNA ligase 1LIG119q13.2-q13.3P18858 details
Cyclic AMP-responsive element-binding protein 1CREB12q34P16220 details
E3 ubiquitin/ISG15 ligase TRIM25TRIM2517q23.2Q14258 details
Concentrations Data
Not Available
HMDB IDHMDB0000045
DrugBank IDDB00131
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030677
KNApSAcK IDC00019347
Chemspider ID5858
KEGG Compound IDC00020
BioCyc IDAMP
BiGG ID33534
Wikipedia LinkAdenylic_acid
METLIN ID5111
PubChem Compound6083
PDB IDNot Available
ChEBI ID16027
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 409 proteins in total.

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Enzymes

Enzyme Details
1. 5'-nucleotidase
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Enzyme Details
2. Cytosolic 5'-nucleotidase 1B
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Enzyme Details
3. Cytosolic 5'-nucleotidase 1A
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Enzyme Details
4. 5'(3')-deoxyribonucleotidase, cytosolic type
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Enzyme Details
5. Deoxycytidine kinase
General function:
Involved in ATP binding
Specific function:
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DCK
Uniprot ID:
P27707
Molecular weight:
30518.315
Enzyme Details
6. 5'(3')-deoxyribonucleotidase, mitochondrial
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Enzyme Details
7. Acetyl-coenzyme A synthetase, cytoplasmic
General function:
Involved in acetate-CoA ligase activity
Specific function:
Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name:
ACSS2
Uniprot ID:
Q9NR19
Molecular weight:
78579.11
Enzyme Details
8. Acetyl-coenzyme A synthetase 2-like, mitochondrial
General function:
Involved in acetate-CoA ligase activity
Specific function:
Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:
ACSS1
Uniprot ID:
Q9NUB1
Molecular weight:
74625.88
Enzyme Details
9. Ectonucleoside triphosphate diphosphohydrolase 1
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Enzyme Details
10. Soluble calcium-activated nucleotidase 1
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24

Transporters

Enzyme Details
1. Very long-chain acyl-CoA synthetase
General function:
Involved in catalytic activity
Specific function:
Acyl-CoA synthetase probably involved in bile acid metabolism. Proposed to activate C27 precurors of bile acids to their CoA thioesters derivatives before side chain cleavage via peroxisomal beta-oxidation occurs. In vitro, activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol. Does not utilize C24 bile acids as substrates. In vitro, also activates long- and branched-chain fatty acids and may have additional roles in fatty acid metabolism. May be involved in translocation of long-chain fatty acids (LFCA) across membranes (By similarity).
Gene Name:
SLC27A2
Uniprot ID:
O14975
Molecular weight:
64614.99
Enzyme Details
2. Transient receptor potential cation channel subfamily M member 2
General function:
Involved in ion channel activity
Specific function:
Nonselective, voltage-independent cation channel mediating sodium and calcium ion influx in response to oxidative stress. Extracellular calcium passes through the channel and acts from the intracellular side as a positive regulator in channel activation. Activated by ADP-ribose, nicotinamide adenine dinucleotide (NAD(+)), reactive nitrogen species and arachidonic acid. Inactivated by intracellular ATP. Confers susceptibility to cell death following oxidative stress. Isoform 2 does not seem to be regulated by ADPR. Has ADP-ribose pyrophosphatase activity.
Gene Name:
TRPM2
Uniprot ID:
O94759
Molecular weight:
171224.9
Enzyme Details
3. Bile acyl-CoA synthetase
General function:
Involved in catalytic activity
Specific function:
Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
Gene Name:
SLC27A5
Uniprot ID:
Q9Y2P5
Molecular weight:
75384.375
Enzyme Details
4. Acyl-CoA synthetase family member 4
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1

Only showing the first 10 proteins. There are 409 proteins in total.

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