2'-deoxyguanosine 5'-monophosphate (CHEBI:16192)

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CHEBI:16192 - 2'-deoxyguanosine 5'-monophosphate

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ChEBI Name	2'-deoxyguanosine 5'-monophosphate

ChEBI ID	CHEBI:16192

Definition	A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42676, CHEBI:42733, CHEBI:42726, CHEBI:41902, CHEBI:41939, CHEBI:41944, CHEBI:47449, CHEBI:19246, CHEBI:10496, CHEBI:14074

Supplier Information	ChemicalBook:CB2692544, eMolecules:31267396, ZINC000001730395

Download	Molfile XML SDF

more structures >>

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Marvin 07260819143D

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Marvin 07260819143D

37 39 0 0 0 0 999 V2000

-4.6360 3.5306 -0.3050 P 0 0 2 0 0 0 0 0 0 0 0 0

-5.7850 2.9768 0.4450 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.7796 4.4933 0.6600 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.1757 4.3767 -1.5640 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.7038 2.3259 -0.8270 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.3553 1.5480 0.3200 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4646 0.3795 -0.1090 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.1549 0.8498 -0.4990 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1730 -0.5541 1.0930 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.2095 -1.5258 1.2480 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8446 -1.2259 0.6670 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2596 -0.2690 -0.3900 C 0 0 2 0 0 0 0 0 0 0 0 0

1.0642 0.1913 0.0350 N 0 0 0 0 0 0 0 0 0 0 0 0

1.3401 1.3460 0.7090 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6200 1.4367 0.9230 N 0 0 0 0 0 0 0 0 0 0 0 0

3.2404 0.3514 0.4020 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5869 -0.0779 0.3370 C 0 0 0 0 0 0 0 0 0 0 0 0

5.4809 0.5939 0.8230 O 0 0 0 0 0 0 0 0 0 0 0 0

4.8573 -1.2536 -0.2720 N 0 0 0 0 0 0 0 0 0 0 0 0

3.8513 -1.9942 -0.8170 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1563 -3.1807 -1.4340 N 0 0 0 0 0 0 0 0 0 0 0 0

2.5965 -1.6071 -0.7630 N 0 0 0 0 0 0 0 0 0 0 0 0

2.2520 -0.4573 -0.1720 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6049 2.0752 1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0

5.7735 -1.5684 -0.3290 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0425 4.8323 0.1340 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7279 5.0860 -1.2090 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.2617 1.1617 0.7860 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8177 2.1723 1.0330 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9292 -0.1765 -0.9240 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0413 0.0206 2.0090 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9245 -2.1290 1.9480 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0368 -2.2055 0.2300 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1712 -1.3124 1.5190 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1839 -0.7790 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4503 -3.7212 -1.8230 H 0 0 0 0 0 0 0 0 0 0 0 0

5.0784 -3.4784 -1.4860 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

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1 4 1 0 0 0 0

1 5 1 0 0 0 0

3 26 1 0 0 0 0

4 27 1 0 0 0 0

5 6 1 0 0 0 0

6 7 1 0 0 0 0

6 28 1 0 0 0 0

6 29 1 0 0 0 0

7 8 1 0 0 0 0

7 9 1 0 0 0 0

7 30 1 0 0 0 0

8 12 1 0 0 0 0

9 10 1 0 0 0 0

9 11 1 0 0 0 0

9 31 1 0 0 0 0

10 32 1 0 0 0 0

11 12 1 0 0 0 0

11 33 1 0 0 0 0

11 34 1 0 0 0 0

12 13 1 0 0 0 0

12 35 1 0 0 0 0

13 14 4 0 0 0 0

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14 15 4 0 0 0 0

14 24 1 0 0 0 0

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16 23 4 0 0 0 0

17 18 2 0 0 0 0

17 19 1 0 0 0 0

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19 25 1 0 0 0 0

20 21 1 0 0 0 0

20 22 2 0 0 0 0

21 36 1 0 0 0 0

21 37 1 0 0 0 0

22 23 1 0 0 0 0

M END): 34 ms

reading 37 atoms

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37 atoms created

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Wikipedia	License
Deoxyguanosine monophosphate (dGMP), also known as deoxyguanylic acid or deoxyguanylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleotide guanosine triphosphate (GTP), in which the –OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). It is used as a monomer in DNA.
Read full article at Wikipedia

Formula

C10H14N5O7P

Net Charge

Average Mass

347.22142

Monoisotopic Mass

347.06308

InChI

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

InChIKey

LTFMZDNNPPEQNG-KVQBGUIXSA-N

SMILES

Nc1nc2n(cnc2c(=O)[nH]1)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) has role Escherichia coli metabolite (CHEBI:76971) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) has role mouse metabolite (CHEBI:75771) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) is a deoxyguanosine phosphate (CHEBI:23625) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) is a guanyl deoxyribonucleotide (CHEBI:63573) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) is a purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:36993) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) is conjugate acid of 2'-deoxyguanosine 5'-monophosphate(2−) (CHEBI:57673) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) is enantiomer of 9-(2-deoxy-5-O-phosphono-β-L-ribofuranosyl)guanine (CHEBI:41945) 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) is tautomer of 2-amino-9-(2-deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol (CHEBI:45049)

Incoming	8,5'-cyclo-2'-deoxyguanosine monophosphate (CHEBI:131829) has functional parent 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) cis-diammine[bis(dGMP)]platinum (CHEBI:76396) has functional parent 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) 2'-deoxyguanosine 5'-monophosphate(2−) (CHEBI:57673) is conjugate base of 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) 9-(2-deoxy-5-O-phosphono-β-L-ribofuranosyl)guanine (CHEBI:41945) is enantiomer of 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) 2'-deoxyguanosine 5'-monophosphate residue (CHEBI:50322) is substituent group from 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) dGMP 3'-end residue (CHEBI:53117) is substituent group from 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) dGMP 5'-end residue (CHEBI:53101) is substituent group from 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192) 2-amino-9-(2-deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol (CHEBI:45049) is tautomer of 2'-deoxyguanosine 5'-monophosphate (CHEBI:16192)

IUPAC Name

2'-deoxy-5'-guanylic acid

Synonyms	Sources
2'-Deoxy-GMP	HMDB
2'-Deoxyguanosine 5'-(dihydrogen phosphate)	HMDB
2'-Deoxyguanosine 5'-monophosphate	KEGG COMPOUND
2'-deoxyguanosine 5'-monophosphate	ChEBI
2'-Deoxyguanosine 5'-phosphate	KEGG COMPOUND
2'-Deoxyguanylic acid	HMDB
2'-dGMP	HMDB
Deoxy-GMP	HMDB
Deoxyguanosine 5'-monophosphate	HMDB
Deoxyguanosine 5'-phosphate	HMDB
Deoxyguanosine monophosphate	KEGG COMPOUND
Deoxyguanylic acid	KEGG COMPOUND
dGMP	KEGG COMPOUND

Manual Xrefs	Databases
C00019356	KNApSAcK
C00362	KEGG COMPOUND
DB04457	DrugBank
Deoxyguanosine_monophosphate	Wikipedia
DGMP	MetaCyc
DGP	PDBeChem
ECMDB01044	ECMDB
HMDB0001044	HMDB
YMDB00506	YMDB
View more database links

Registry Numbers	Types	Sources
58430	Reaxys Registry Number	Reaxys
902-04-5	CAS Registry Number	KEGG COMPOUND
902-04-5	CAS Registry Number	ChemIDplus

Citations

Li M, Sun H, Feng Q, Lu H, Zhao Y, Zhang H, Xu X, Jiao J, Wang L, Hua Y (2013)
Extracellular dGMP enhances Deinococcus radiodurans tolerance to oxidative stress.
PloS one 8, e54420 [PubMed:23365666]
[show Abstract]

Nielsen JB, Thøgersen J, Jensen SK, Nielsen SB, Keiding SR (2011)
Vibrational dynamics of deoxyguanosine 5'-monophosphate following UV excitation.
Physical chemistry chemical physics : PCCP 13, 13821-13826 [PubMed:21720611]
[show Abstract]

Miannay FA, Gustavsson T, Banyasz A, Markovitsi D (2010)
Excited-state dynamics of dGMP measured by steady-state and femtosecond fluorescence spectroscopy.
The journal of physical chemistry. A 114, 3256-3263 [PubMed:20085298]
[show Abstract]

Kurihara T, Motohashi N, Kobayashi H, Yamanaka W, Dohyashiki S, Molnár J (1998)
Interaction of chlorpromazine with 2'-deoxyguanosine-5'-monophosphate by PM3 calculation.
Anticancer research 18, 3493-3497 [PubMed:9858930]
[show Abstract]

Munns TW, Freeman SK (1989)
Antibody-nucleic acid complexes. Oligo(dG)n and -(dT)n specificities associated with anti-DNA antibodies from autoimmune MRL mice.
Biochemistry 28, 10048-10054 [PubMed:2559771]
[show Abstract]

O'DONNELL JF, MACKAL RP, EVANS EA (1958)
An analysis of the acid-soluble fraction of normal and T2r-infected cells of Escherichia coli, strain B.
The Journal of biological chemistry 233, 1523-1527 [PubMed:13610867]

Last Modified

05 December 2017

CHEBI:16192 - 2'-deoxyguanosine 5'-monophosphate

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