guanosine 5'-[beta,gamma-imido]triphosphate (CHEBI:78408)

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CHEBI:78408 - guanosine 5'-[β,γ-imido]triphosphate

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ChEBI Name	guanosine 5'-[β,γ-imido]triphosphate

ChEBI ID	CHEBI:78408

ChEBI ASCII Name	guanosine 5'-[beta,gamma-imido]triphosphate

Definition	A nucleoside triphosphate analogue that is GTP in which the oxygen atom bridging the β- to the γ- phosphate is replaced by a nitrogen atom A non-hydrolyzable analog of GTP, it binds tightly to G-protein in the presence of Mg²⁺.

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

Secondary ChEBI IDs	CHEBI:42862

Supplier Information	ZINC000037868676

Download	Molfile XML SDF

more structures >>

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Mrv0541 08111415193D

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Mrv0541 08111415193D

49 51 0 0 0 0 999 V2000

-1.2310 -0.2950 7.2120 P 0 0 2 0 0 0 0 0 0 0 0 0

-1.7590 1.0780 7.0630 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1580 -1.1180 8.2400 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2740 -0.2340 7.7780 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2360 -1.0640 5.7140 N 0 0 2 0 0 0 0 0 0 0 0 0

-0.2520 -0.1510 4.6990 P 0 0 1 0 0 0 0 0 0 0 0 0

-0.7950 1.2210 4.5890 O 0 0 0 0 0 0 0 0 0 0 0 0

1.2370 -0.0910 5.3070 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2090 -0.8300 3.2400 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7440 0.0890 2.3260 P 0 0 1 0 0 0 0 0 0 0 0 0

0.1850 1.4580 2.2520 O 0 0 0 0 0 0 0 0 0 0 0 0

2.2160 0.1450 2.9740 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.3520 0.1880 -4.1660 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.3150 1.0510 -3.7300 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1960 1.2400 -4.6680 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.8530 0.5120 -5.7590 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4230 0.3300 -7.0410 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4530 0.9020 -7.3540 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.7940 -0.4890 -7.9120 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.6460 -1.1290 -7.5490 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0330 -1.9600 -8.4530 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.1070 -0.9680 -6.3610 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.6700 -0.1680 -5.4490 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1660 -0.6300 -8.7970 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3410 1.5090 -2.7520 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8320 -0.5340 0.8450 O 0 0 0 0 0 0 0 0 0 0 0 0

1.6880 0.3220 0.0860 C 0 0 1 0 0 0 0 0 0 0 0 0

1.8150 -0.2170 -1.3390 C 0 0 1 0 0 0 0 0 0 0 0 0

0.5240 -0.2370 -1.9860 O 0 0 0 0 0 0 0 0 0 0 0 0

2.6740 0.7340 -2.2020 C 0 0 1 0 0 0 0 0 0 0 0 0

4.0180 0.2580 -2.2850 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9970 0.6950 -3.5920 C 0 0 1 0 0 0 0 0 0 0 0 0

2.9040 0.1960 -4.5770 O 0 0 0 0 0 0 0 0 0 0 0 0

0.8080 -0.2720 -3.4020 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.1270 -0.6450 9.0830 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5790 -1.1470 7.8600 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1750 -0.9880 5.3530 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5530 -1.0040 5.3620 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5430 -0.7640 3.0040 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2650 1.3260 0.0580 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6730 0.3560 0.5510 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2510 -1.2160 -1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6520 1.7440 -1.7930 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5050 0.8890 -2.8330 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6390 1.6860 -3.8710 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6510 0.8100 -4.6060 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0870 -1.2810 -3.7080 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7860 -2.4190 -8.2100 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4210 -2.0920 -9.3320 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

1 5 1 0 0 0 0

3 35 1 0 0 0 0

4 36 1 0 0 0 0

5 6 1 0 0 0 0

5 37 1 0 0 0 0

6 7 2 0 0 0 0

6 8 1 0 0 0 0

6 9 1 0 0 0 0

8 38 1 0 0 0 0

9 10 1 0 0 0 0

10 11 2 0 0 0 0

10 12 1 0 0 0 0

10 26 1 0 0 0 0

12 39 1 0 0 0 0

13 14 4 0 0 0 0

13 23 4 0 0 0 0

14 15 4 0 0 0 0

14 25 1 0 0 0 0

15 16 4 0 0 0 0

16 17 1 0 0 0 0

16 23 4 0 0 0 0

17 18 2 0 0 0 0

17 19 1 0 0 0 0

19 20 1 0 0 0 0

19 24 1 0 0 0 0

20 21 1 0 0 0 0

20 22 2 0 0 0 0

21 48 1 0 0 0 0

21 49 1 0 0 0 0

22 23 1 0 0 0 0

26 27 1 0 0 0 0

27 28 1 0 0 0 0

27 40 1 0 0 0 0

27 41 1 0 0 0 0

28 29 1 0 0 0 0

28 30 1 0 0 0 0

28 42 1 0 0 0 0

29 34 1 0 0 0 0

30 31 1 0 0 0 0

30 32 1 0 0 0 0

30 43 1 0 0 0 0

31 44 1 0 0 0 0

32 33 1 0 0 0 0

32 34 1 0 0 0 0

32 45 1 0 0 0 0

33 46 1 0 0 0 0

34 13 1 0 0 0 0

34 47 1 0 0 0 0

M END): 16 ms

reading 49 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

49 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

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Formula

C10H17N6O13P3

Net Charge

Average Mass

522.19570

Monoisotopic Mass

522.00665

InChI

InChI=1S/C10H17N6O13P3/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24)/t3-,5-,6-,9-/m1/s1

InChIKey

UQABYHGXWYXDTK-UUOKFMHZSA-N

SMILES

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

ChEBI Ontology
Outgoing	guanosine 5'-[β,γ-imido]triphosphate (CHEBI:78408) is a nucleoside triphosphate analogue (CHEBI:37413) guanosine 5'-[β,γ-imido]triphosphate (CHEBI:78408) is conjugate acid of guanosine 5'-[β,γ-imido]triphosphate(4−) (CHEBI:78409)

Incoming	guanosine 5'-[β,γ-imido]triphosphate(4−) (CHEBI:78409) is conjugate base of guanosine 5'-[β,γ-imido]triphosphate (CHEBI:78408)

IUPAC Name

5'-O-(hydroxy{[hydroxy(phosphonoamino)phosphoryl]oxy}phosphoryl)guanosine

Synonyms	Sources
5'-Guanylic acid, monoanhydride with imidodiphosphoric acid	ChemIDplus
5'-guanylylimidodiphosphate	ChEBI
GMP-PNP	ChEBI
GMP-Pnp	ChemIDplus
Gpp(NH)-p	ChEBI
Gpp(NH)p	ChEBI
Guanylyl imidodiphosphate	ChemIDplus

Manual Xrefs	Databases
5'-Guanylyl imidodiphosphate	Wikipedia
GNP	PDBeChem
View more database links

Registry Numbers	Types	Sources
1201190	Reaxys Registry Number	Reaxys
34273-04-6	CAS Registry Number	ChemIDplus

Citations

Arata Y, Tada S, Ui M (1992)
Probable occurrence of toxin-susceptible G proteins in the nematode Caenorhabditis elegans.
FEBS letters 300, 73-76 [PubMed:1547891]
[show Abstract]

Fukushima O, Gay CV (1991)
Ultrastructural localization of guanylate cyclase in bone cells.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 39, 529-535 [PubMed:1672318]
[show Abstract]

Steinberg SF, Chow YK, Bilezikian JP (1987)
Stimulatory and inhibitory regulation of myocardial adenylate cyclase by 5'-guanylyl-imidodiphosphate.
Biochemical pharmacology 36, 757-764 [PubMed:3103629]
[show Abstract]

Aleksandrowicz Z (1985)
Mitochondrial adenosine triphosphatase from human placenta--effects of adenylyl and guanylyl imidodiphosphate.
The International journal of biochemistry 17, 229-234 [PubMed:3159604]
[show Abstract]

Treistman SN, Levitan IB (1976)
Intraneuronal guanylyl-imidodiphosphate injection mimics long-term synaptic hyperpolarization in Aplysia.
Proceedings of the National Academy of Sciences of the United States of America 73, 4689-4692 [PubMed:188052]
[show Abstract]

Lefkowitz RJ, Caron MG (1975)
Characteristics of 5'-guanylyl imidodiphosphate-activated adenylate cyclase.
The Journal of biological chemistry 250, 4418-4422 [PubMed:166994]
[show Abstract]

Londos C, Salomon Y, Lin MC, Harwood JP, Schramm M, Wolff J, Rodbell M (1974)
5'-Guanylylimidodiphosphate, a potent activator of adenylate cyclase systems in eukaryotic cells.
Proceedings of the National Academy of Sciences of the United States of America 71, 3087-3090 [PubMed:4607368]
[show Abstract]

Last Modified

11 August 2014

CHEBI:78408 - guanosine 5'-[β,γ-imido]triphosphate

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