Cannabis Compound Database: Showing Compound Card for 2'-Deoxyguanosine 5'-monophosphate (CDB004877)

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Record Information

Version

1.0

Created at

2020-04-17 18:46:02 UTC

Updated at

2020-11-18 16:38:55 UTC

CannabisDB ID

CDB004877

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2'-Deoxyguanosine 5'-monophosphate

Description

2'-Deoxyguanosine 5'-monophosphate, also known as deoxyguanylic acid or 2'-deoxy-GMP, 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. 2'-Deoxyguanosine 5'-monophosphate is a moderately basic compound (based on its pKa). 2'-Deoxyguanosine 5'-monophosphate exists in all living species, ranging from bacteria to humans. Within humans, 2'-deoxyguanosine 5'-monophosphate participates in a number of enzymatic reactions. In particular, 2'-deoxyguanosine 5'-monophosphate can be converted into dGDP; which is mediated by the enzyme guanylate kinase. In addition, 2'-deoxyguanosine 5'-monophosphate can be converted into deoxyguanosine through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In humans, 2'-deoxyguanosine 5'-monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase. 2'-Deoxyguanosine 5'-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'-Deoxy-GMP	ChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphate)	ChEBI
2'-Deoxyguanosine 5'-phosphate	ChEBI
2'-Deoxyguanylic acid	ChEBI
2'-dGMP	ChEBI
Deoxy-GMP	ChEBI
Deoxyguanosine 5'-monophosphate	ChEBI
Deoxyguanosine 5'-phosphate	ChEBI
Deoxyguanosine monophosphate	ChEBI
Deoxyguanylic acid	ChEBI
dGMP	ChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphoric acid)	Generator
2'-Deoxyguanosine 5'-phosphoric acid	Generator
2'-Deoxyguanylate	Generator
Deoxyguanosine 5'-monophosphoric acid	Generator
Deoxyguanosine 5'-phosphoric acid	Generator
Deoxyguanosine monophosphoric acid	Generator
Deoxyguanylate	Generator
2'-Deoxyguanosine 5'-monophosphoric acid	Generator
2'-Deoxy-5'-GMP	HMDB
2'-Deoxy-5'-guanylate	HMDB
2'-Deoxy-5'-guanylic acid	HMDB
2'-Deoxy-guanosine 5'-(dihydrogen phosphate)	HMDB
2'-Deoxy-guanosine 5'-phosphate	HMDB
2'-Deoxy-guanosine phosphate	HMDB
2'-Deoxyguanosine-5'-phosphate	HMDB
2'-DG-5'-MP	HMDB
Deoxyguanosine-phosphate	HMDB
Guanine riboside	HMDB
2'-Deoxyguanosine 5'-phosphate, ion (1+)	HMDB
2'-Deoxyguanosine 5'-phosphate, disodium salt	HMDB

Chemical Formula

C₁₀H₁₄N₅O₇P

Average Molecular Weight

347.22

Monoisotopic Molecular Weight

347.0631

IUPAC Name

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

Traditional Name

deoxyguanylate

CAS Registry Number

902-04-5

SMILES

NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1

InChI Identifier

InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1

InChI Key

LTFMZDNNPPEQNG-KVQBGUIXSA-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
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

deoxyguanosine phosphate (CHEBI:16192 )
purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:16192 )
guanyl deoxyribonucleotide (CHEBI:16192 )
Deoxyribonucleotides (C00362 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	-1.9	ALOGPS
logP	-2.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	2.62	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.55 m³·mol⁻¹	ChemAxon
Polarizability	29.72 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
Predicted GC-MS	2'-Deoxyguanosine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9412000000-b0aa92c3ffa6b5b0890c	Spectrum
Predicted GC-MS	2'-Deoxyguanosine 5'-monophosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dm-9422100000-bc551a9549f9ae975b71	Spectrum
Predicted GC-MS	2'-Deoxyguanosine 5'-monophosphate, non-derivatized, 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)	splash10-0fr2-0598000000-21b063e2aff7146d8568	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-d2858e957ac8a4c91e79	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004j-9203000000-40bcf8d5e1ae6813c4f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004j-9203000000-40bcf8d5e1ae6813c4f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-dab30b9a6de3477fa70e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-002b-6109000000-6e5f13e1030d907bf450	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-c3273057674f4f74157b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-002b-6009000000-303a1b69aa5c35e59b53	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-5a760c04146b7ec031d7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-d435ed7c5cdb98529682	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-41c0a9342f54a46fa4e4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-68f72700dfdbb0374a85	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0905000000-26458e3261a5441d9304	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-1900000000-7a7e7e8e0b0145b7230d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-a0ce6815866f122bcce0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0901000000-415ae3ba37bc56d4a402	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-bd375d50d1fb3f236468	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-6585941fd6af257d9a96	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-303e1f2bb06730d8520d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0901000000-e4234086a26601ce5af3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-566d720734de1bad5cd6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-5d4689698c352d2a2f45	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-6309000000-10f0b25fe6368edd1660	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-d531006102bbcb9090d1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-a08be881b0ccce87df8a	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 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
Inosine triphosphate pyrophosphatase	ITPA	20p	Q9BY32	details
Deoxyguanosine kinase, mitochondrial	DGUOK	2p13	Q16854	details
Guanylate kinase	GUK1	1q32-q41	Q16774	details
Cytosolic 5'-nucleotidase 3	NT5C3	7p14.3	Q9H0P0	details
Cytosolic purine 5'-nucleotidase	NT5C2	10q24.32	P49902	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
Inosine triphosphate pyrophosphatase	ITPA	20p	Q9BY32	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

HMDB0001044

DrugBank ID

DB04457

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Deoxyguanosine_monophosphate

METLIN ID

Not Available

PubChem Compound

65059

PDB ID

Not Available

ChEBI ID

16192

References

General References

Not Available

Only showing the first 10 proteins. There are 18 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. Inosine triphosphate pyrophosphatase

General function:: Involved in hydrolase activity
Specific function:: Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:: ITPA
Uniprot ID:: Q9BY32
Molecular weight:: 16833.23

Enzyme Details

7. Deoxyguanosine kinase, mitochondrial

General function:: Involved in ATP binding
Specific function:: Required for the phosphorylation of several deoxyribonucleosides and certain nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:: DGUOK
Uniprot ID:: Q16854
Molecular weight:: 32055.53

Enzyme Details

8. Guanylate kinase

General function:: Involved in guanylate kinase activity
Specific function:: Essential for recycling GMP and indirectly, cGMP.
Gene Name:: GUK1
Uniprot ID:: Q16774
Molecular weight:: 21725.41

Enzyme Details

9. 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

Enzyme Details

10. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

Only showing the first 10 proteins. There are 18 proteins in total.

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Showing Compound Card for 2'-Deoxyguanosine 5'-monophosphate (CDB004877)

Structure for CDB004877 (2'-Deoxyguanosine 5'-monophosphate)

Enzymes