Cannabis Compound Database: Showing Compound Card for Deoxyadenosine monophosphate (CDB004870)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (12) Show 19 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:45:17 UTC

Updated at

2020-11-18 16:38:54 UTC

CannabisDB ID

CDB004870

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Deoxyadenosine monophosphate

Description

Deoxyadenosine monophosphate, also known as deoxyadenylic acid or 2'-dAMP, belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Deoxyadenosine monophosphate is a strong basic compound (based on its pKa). Deoxyadenosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, deoxyadenosine monophosphate participates in a number of enzymatic reactions. In particular, deoxyadenosine monophosphate can be converted into dADP through the action of the enzyme adenylate kinase isoenzyme 1. In addition, deoxyadenosine monophosphate can be converted into deoxyadenosine; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. In humans, deoxyadenosine monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase. Deoxyadenosine monophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2'-dAMP	ChEBI
2'-Deoxy-5'-adenosine monophosphate	ChEBI
2'-Deoxy-AMP	ChEBI
2'-Deoxyadenosine 5'-(dihydrogen phosphate)	ChEBI
2'-Deoxyadenosine 5'-phosphate	ChEBI
2'-Deoxyadenosine monophosphate	ChEBI
2'-DEOXYADENOSINE-5'-monophosphATE	ChEBI
2'-Deoxyadenylic acid	ChEBI
dAMP	ChEBI
Deoxy-5'-adenylic acid	ChEBI
Deoxy-AMP	ChEBI
Deoxyadenosine 5'-monophosphate	ChEBI
Deoxyadenosine 5'-phosphate	ChEBI
Deoxyadenylic acid	ChEBI
2'-Deoxyadenosine 5'-monophosphate	Kegg
2'-Deoxy-5'-adenosine monophosphoric acid	Generator
2'-Deoxyadenosine 5'-(dihydrogen phosphoric acid)	Generator
2'-Deoxyadenosine 5'-phosphoric acid	Generator
2'-Deoxyadenosine monophosphoric acid	Generator
2'-DEOXYADENOSINE-5'-monophosphoric acid	Generator
2'-Deoxyadenylate	Generator
Deoxy-5'-adenylate	Generator
Deoxyadenosine 5'-monophosphoric acid	Generator
Deoxyadenosine 5'-phosphoric acid	Generator
Deoxyadenylate	Generator
2'-Deoxyadenosine 5'-monophosphoric acid	Generator
Deoxyadenosine monophosphoric acid	Generator
2'-Deoxy-5'-adenylate	HMDB
2'-Deoxy-5'-adenylic acid	HMDB
2'-Deoxy-adenosine 5'-phosphorate	HMDB
2'-Deoxy-adenosine 5'-phosphoric acid	HMDB
2'-Deoxyadenosine-5'-phosphate	HMDB
Deoxyadenosine-phosphate	HMDB
PdA	HMDB
2'-Deoxy-5'-adenosine monophosphate, ammonium salt	HMDB
2'-Deoxy-5'-adenosine monophosphate, disodium salt	HMDB
2'Deoxy-5'-AMP	HMDB
dAMP CPD	HMDB

Chemical Formula

C₁₀H₁₄N₅O₆P

Average Molecular Weight

331.22

Monoisotopic Molecular Weight

331.0682

IUPAC Name

{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

DAMP

CAS Registry Number

653-63-4

SMILES

NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

InChI Identifier

InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1

InChI Key

KHWCHTKSEGGWEX-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine deoxyribonucleotides

Direct Parent

Purine 2'-deoxyribonucleoside monophosphates

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside monophosphate
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Imidolactam
Alkyl phosphate
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:17713 )
2'-deoxyadenosine 5'-phosphate (CHEBI:17713 )
Deoxyribonucleotides (C00360 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Subcellular:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	148 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-3.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	3.94	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	165.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.56 m³·mol⁻¹	ChemAxon
Polarizability	28.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Deoxyadenosine monophosphate, 6 TMS, GC-MS Spectrum	splash10-001i-9210000000-52089369f69d88f5ea1c	Spectrum
GC-MS	Deoxyadenosine monophosphate, non-derivatized, GC-MS Spectrum	splash10-001i-9210000000-52089369f69d88f5ea1c	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0005-9601000000-2ae616924ca1385b9693	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ow-9433000000-7d0506e58e284d44779c	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxyadenosine monophosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0089-4096000000-d903c4b1613b2ac5f708	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9010000000-c50cec0a2ca71d42d524	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9300000000-8ebf385d33982fcaef9f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-0209000000-05ded3b31c4db3d6c016	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0019-1907000000-50567fa8c2638c9e2b6f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-003r-9804000000-9196bd87057cc65827a3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-003r-9804000000-9196bd87057cc65827a3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0209000000-05ded3b31c4db3d6c016	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0019-1907000000-50567fa8c2638c9e2b6f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-2900000000-7eab9e6d466f6f6fc5ca	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0019-1907000000-50567fa8c2638c9e2b6f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0019-4900000000-7e54c832e11165a43f06	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-6900000000-2a484df957d9a58803cd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-4930000000-881e3633ecf1832b39c1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0921000000-913b60e77094a1a288c9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-ee54193845dfdd45afd8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-1900000000-700554bbc39a72147ed1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9500000000-f0950c77946a8c1b5112	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1930000000-a75e389060d82c5d0b7f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0901000000-2d08f4128523b3afc5f3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-3c531326eee979b1f9a3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-e832807c09bda720138b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-6309000000-3c3e22257c611faa9f07	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-2304362c6bf7c8e4aa49	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-f628177d4207cc1a2c0b	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
5'-nucleotidase	NT5E	6q14-q21	P21589	details
Cytosolic 5'-nucleotidase 1B	NT5C1B	2p24.2	Q96P26	details
Cytosolic 5'-nucleotidase 1A	NT5C1A	1p34.3-p33	Q9BXI3	details
5'(3')-deoxyribonucleotidase, cytosolic type	NT5C		Q8TCD5	details
5'(3')-deoxyribonucleotidase, mitochondrial	NT5M		Q9NPB1	details
Adenylate kinase isoenzyme 1	AK1	9q34.1	P00568	details
Adenylate kinase isoenzyme 4, mitochondrial	AK4	1p31.3	P27144	details
Adenylate kinase 7	AK7	14q32.2	Q96M32	details
Adenylate kinase isoenzyme 5	AK5	1p31	Q9Y6K8	details
Cytosolic 5'-nucleotidase 3	NT5C3	7p14.3	Q9H0P0	details
Cytosolic purine 5'-nucleotidase	NT5C2	10q24.32	P49902	details
Adenylate kinase 2, mitochondrial	AK2	1p34	P54819	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
5'-nucleotidase	NT5E	6q14-q21	P21589	details
Cytosolic 5'-nucleotidase 1B	NT5C1B	2p24.2	Q96P26	details
Cytosolic 5'-nucleotidase 1A	NT5C1A	1p34.3-p33	Q9BXI3	details
5'(3')-deoxyribonucleotidase, cytosolic type	NT5C		Q8TCD5	details
5'(3')-deoxyribonucleotidase, mitochondrial	NT5M		Q9NPB1	details
Cytosolic 5'-nucleotidase 3	NT5C3	7p14.3	Q9H0P0	details
Cytosolic purine 5'-nucleotidase	NT5C2	10q24.32	P49902	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000905

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022311

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Deoxyadenosine_monophosphate

METLIN ID

3461

PubChem Compound

12599

PDB ID

Not Available

ChEBI ID

17713

References

General References

Not Available

Only showing the first 10 proteins. There are 19 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. 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

6. Adenylate kinase isoenzyme 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth.
Gene Name:: AK1
Uniprot ID:: P00568
Molecular weight:: 21634.725

Enzyme Details

7. Adenylate kinase isoenzyme 4, mitochondrial

General function:: Involved in ATP binding
Specific function:: Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. May also be active with GTP (By similarity).
Gene Name:: AK4
Uniprot ID:: P27144
Molecular weight:: 25267.83

Enzyme Details

8. Adenylate kinase 7

General function:: Involved in ATP binding
Specific function:: Adenylate kinase involved in maintaining ciliary structure and function (By similarity). Has highest activity toward AMP, and weaker activity toward dAMP, CMP and dCMP.
Gene Name:: AK7
Uniprot ID:: Q96M32
Molecular weight:: 82657.68

Enzyme Details

9. Adenylate kinase isoenzyme 5

General function:: Involved in ATP binding
Specific function:: Active on AMP and dAMP with ATP as a donor. When GTP is used as phosphate donor, the enzyme phosphorylates AMP, CMP, and to a small extent dCMP.
Gene Name:: AK5
Uniprot ID:: Q9Y6K8
Molecular weight:: 60313.985

Enzyme Details

10. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Only showing the first 10 proteins. There are 19 proteins in total.

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Showing Compound Card for Deoxyadenosine monophosphate (CDB004870)

Structure for CDB004870 (Deoxyadenosine monophosphate)

Enzymes