dATP (CHEBI:16284)

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CHEBI:16284 - dATP

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ChEBI Name	dATP

ChEBI ID	CHEBI:16284

Definition	A purine 2'-deoxyribonucleoside 5'-triphosphate having adenine as the nucleobase.

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

Secondary ChEBI IDs	CHEBI:19238, CHEBI:42290, CHEBI:10491, CHEBI:14069

Supplier Information	eMolecules:30512965, ZINC000008215662

Download	Molfile XML SDF

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The Resolver thinks Mol

DTP - Ideal conformer

Mrv1927 07272109333D

starting HoverWatcher_5

Time for openFile(DTP - Ideal conformer

Mrv1927 07272109333D

46 48 0 0 0 0 999 V2000

1.1730 -0.2530 -6.6990 P 0 0 2 0 0 5 0 0 0 0 0 0

1.9470 0.9790 -6.4310 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9490 -1.1480 -7.7890 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2810 0.1390 -7.2650 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2290 -0.1410 -4.2950 P 0 0 2 0 0 5 0 0 0 0 0 0

-1.0940 0.2170 -4.8530 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0860 1.1970 -4.0430 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0090 -1.0920 -5.3340 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.7520 0.0820 -1.9140 P 0 0 1 0 0 5 0 0 0 0 0 0

0.0500 1.3090 -1.7200 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1750 0.4680 -2.5610 O 0 0 0 0 0 0 0 0 0 0 0 0

0.0290 -0.9210 -2.9000 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9870 -0.6360 -0.4930 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.6820 0.2980 0.3330 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.9370 -0.3250 1.7070 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.6920 -0.5550 2.4040 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.6910 0.6690 2.6260 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.1030 0.5770 2.4280 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2980 0.1680 4.0370 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.0090 -0.6430 3.8040 C 0 0 2 0 0 0 0 0 0 0 0 0

0.0840 -0.0780 4.5980 N 0 0 0 0 0 0 0 0 0 0 0 0

0.9490 0.8980 4.2010 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7940 1.1570 5.1560 N 0 0 0 0 0 0 0 0 0 0 0 0

1.5240 0.3700 6.2250 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0910 0.2060 7.5000 C 0 0 0 0 0 0 0 0 0 0 0 0

3.1760 0.9680 7.8950 N 0 0 0 0 0 0 0 0 0 0 0 0

1.5580 -0.6940 8.3190 N 0 0 0 0 0 0 0 0 0 0 0 0

0.5230 -1.4260 7.9500 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0360 -1.3100 6.7640 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4270 -0.4360 5.8780 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0260 -0.6100 -8.5880 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7520 -0.6900 -7.4260 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9390 0.9190 -3.6810 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6660 -0.3570 -2.6700 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6340 0.5570 -0.1300 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0780 1.1990 0.4500 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4970 -1.2550 1.6060 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3430 1.6890 2.4640 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.5160 1.1490 3.0900 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0810 -0.4690 4.4470 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1040 1.0100 4.7010 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1700 -1.6840 4.0830 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9340 1.3840 3.2370 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5570 0.8490 8.7800 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5590 1.6200 7.2870 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1210 -2.1460 8.6470 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 8 1 0 0 0 0

3 31 1 0 0 0 0

4 32 1 0 0 0 0

5 6 2 0 0 0 0

5 7 1 1 0 0 0

5 8 1 0 0 0 0

5 12 1 0 0 0 0

7 33 1 0 0 0 0

9 10 2 0 0 0 0

9 11 1 6 0 0 0

9 12 1 0 0 0 0

9 13 1 0 0 0 0

11 34 1 0 0 0 0

13 14 1 0 0 0 0

14 15 1 0 0 0 0

14 35 1 0 0 0 0

14 36 1 0 0 0 0

15 16 1 0 0 0 0

15 17 1 0 0 0 0

15 37 1 6 0 0 0

16 20 1 0 0 0 0

17 18 1 0 0 0 0

17 19 1 0 0 0 0

17 38 1 6 0 0 0

18 39 1 0 0 0 0

19 20 1 0 0 0 0

19 40 1 0 0 0 0

19 41 1 0 0 0 0

20 21 1 0 0 0 0

20 42 1 1 0 0 0

21 22 1 0 0 0 0

21 30 1 0 0 0 0

22 23 2 0 0 0 0

22 43 1 0 0 0 0

23 24 1 0 0 0 0

24 25 1 0 0 0 0

24 30 2 0 0 0 0

25 26 1 0 0 0 0

25 27 2 0 0 0 0

26 44 1 0 0 0 0

26 45 1 0 0 0 0

27 28 1 0 0 0 0

28 29 2 0 0 0 0

28 46 1 0 0 0 0

29 30 1 0 0 0 0

M END): 18 ms

reading 46 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

46 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Deoxyadenosine triphosphate (dATP) is a nucleotide used in cells for DNA synthesis (or replication), as a substrate of DNA polymerase. Deoxyadenosine triphosphate is produced from DNA by the action of nuclease P1, adenylate kinase, and pyruvate kinase.
Read full article at Wikipedia

Formula

C10H16N5O12P3

Net Charge

Average Mass

491.182

Monoisotopic Mass

491.00083

InChI

InChI=1S/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1

InChIKey

SUYVUBYJARFZHO-RRKCRQDMSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	Found in whole organism (UBERON:0000468). From MetaboLights See: MetaboLights Study

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). (via nucleoside 5'-triphoshate )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	dATP (CHEBI:16284) has role Escherichia coli metabolite (CHEBI:76971) dATP (CHEBI:16284) has role mouse metabolite (CHEBI:75771) dATP (CHEBI:16284) is a 2'-deoxyadenosine 5'-phosphate (CHEBI:19237) dATP (CHEBI:16284) is a purine 2'-deoxyribonucleoside 5'-triphosphate (CHEBI:37042) dATP (CHEBI:16284) is conjugate acid of dATP(3−) (CHEBI:495505)

Incoming	dATP(3−) (CHEBI:495505) is conjugate base of dATP (CHEBI:16284)

IUPAC Name

2'-deoxyadenosine 5'-(tetrahydrogen triphosphate)

Synonyms	Sources
2'-dATP	ChemIDplus
2'-deoxy-ATP	ChEBI
2'-Deoxyadenosine 5'-triphosphate	KEGG COMPOUND
2'-deoxyadenosine 5'-triphosphate	ChEBI
2'-deoxyadenosine triphosphate	ChemIDplus
dATP	KEGG COMPOUND
Deoxyadenosine 5'-triphosphate	KEGG COMPOUND
Deoxyadenosine triphosphate	KEGG COMPOUND

Manual Xrefs	Databases
15194	ChemSpider
C00131	KEGG COMPOUND
DB03222	DrugBank
Deoxyadenosine_triphosphate	Wikipedia
DTP	PDBeChem
FDB022674	FooDB
HMDB0001532	HMDB
View more database links

Registry Number	Type	Source
1927-31-7	CAS Registry Number	ChemIDplus

Citations

McCabe KJ, Aboelkassem Y, Teitgen AE, Huber GA, McCammon JA, Regnier M, McCulloch AD (2020)
Predicting the effects of dATP on cardiac contraction using multiscale modeling of the sarcomere.
Archives of biochemistry and biophysics 695, 108582 [PubMed:32956632]
[show Abstract]

Sun SQ, Chen SL (2020)
An Unprecedented Ring-Contraction Mechanism in Cobalamin-Dependent Radical S-Adenosylmethionine Enzymes.
The journal of physical chemistry letters 11, 6812-6818 [PubMed:32787210]
[show Abstract]

Ma W, Childers M, Murray J, Moussavi-Harami F, Gong H, Weiss R, Daggett V, Irving T, Regnier M (2020)
Myosin dynamics during relaxation in mouse soleus muscle and modulation by 2'-deoxy-ATP.
The Journal of physiology 598, 5165-5182 [PubMed:32818298]
[show Abstract]

Key points

Skeletal muscle relaxation has been primarily studied by assessing the kinetics of force decay. Little is known about the resultant dynamics of structural changes in myosin heads during relaxation. The naturally occurring nucleotide 2-deoxy-ATP (dATP) is a myosin activator that enhances cross-bridge binding and kinetics. X-ray diffraction data indicate that with elevated dATP, myosin heads were extended closer to actin in relaxed muscle and myosin heads return to an ordered, resting state after contraction more quickly. Molecular dynamics simulations of post-powerstroke myosin suggest that dATP induces structural changes in myosin heads that increase the surface area of the actin-binding regions promoting myosin interaction with actin, which could explain the observed delays in the onset of relaxation. This study of the dATP-induced changes in myosin may be instructive for determining the structural changes desired for other potential myosin-targeted molecular compounds to treat muscle diseases.

Abstract

Here we used time-resolved small-angle X-ray diffraction coupled with force measurements to study the structural changes in FVB mouse skeletal muscle sarcomeres during relaxation after tetanus contraction. To estimate the rate of myosin deactivation, we followed the rate of the intensity recovery of the first-order myosin layer line (MLL1) and restoration of the resting spacing of the third and sixth order of meridional reflection (S_M3 and S_M6 ) following tetanic contraction. A transgenic mouse model with elevated skeletal muscle 2-deoxy-ATP (dATP) was used to study how myosin activators may affect soleus muscle relaxation. X-ray diffraction evidence indicates that with elevated dATP, myosin heads were extended closer to actin in resting muscle. Following contraction, there is a slight but significant delay in the decay of force relative to WT muscle while the return of myosin heads to an ordered resting state was initially slower, then became more rapid than in WT muscle. Molecular dynamics simulations of post-powerstroke myosin suggest that dATP induces structural changes in myosin that increase the surface area of the actin-binding regions, promoting myosin interaction with actin. With dATP, myosin heads may remain in an activated state near the thin filaments following relaxation, accounting for the delay in force decay and the initial delay in recovery of resting head configuration, and this could facilitate subsequent contractions.

Powers JD, Yuan CC, McCabe KJ, Murray JD, Childers MC, Flint GV, Moussavi-Harami F, Mohran S, Castillo R, Zuzek C, Ma W, Daggett V, McCulloch AD, Irving TC, Regnier M (2019)
Cardiac myosin activation with 2-deoxy-ATP via increased electrostatic interactions with actin.
Proceedings of the National Academy of Sciences of the United States of America 116, 11502-11507 [PubMed:31110001]
[show Abstract]

Parker MJ, Maggiolo AO, Thomas WC, Kim A, Meisburger SP, Ando N, Boal AK, Stubbe J (2018)
An endogenous dAMP ligand in Bacillus subtilis class Ib RNR promotes assembly of a noncanonical dimer for regulation by dATP.
Proceedings of the National Academy of Sciences of the United States of America 115, E4594-E4603 [PubMed:29712847]
[show Abstract]

Cheng Y, Hogarth KA, O'Sullivan ML, Regnier M, Pyle WG (2016)
2-Deoxyadenosine triphosphate restores the contractile function of cardiac myofibril from adult dogs with naturally occurring dilated cardiomyopathy.
American journal of physiology. Heart and circulatory physiology 310, H80-91 [PubMed:26497964]
[show Abstract]

Ando N, Li H, Brignole EJ, Thompson S, McLaughlin MI, Page JE, Asturias FJ, Stubbe J, Drennan CL (2016)
Allosteric Inhibition of Human Ribonucleotide Reductase by dATP Entails the Stabilization of a Hexamer.
Biochemistry 55, 373-381 [PubMed:26727048]
[show Abstract]

Nayak S, Bryant FR (2015)
Kinetics of the ATP and dATP-mediated formation of a functionally-active RecA-ssDNA complex.
Biochemical and biophysical research communications 463, 1257-1261 [PubMed:26100204]
[show Abstract]

Kim J, Wang L, Li Y, Becnel KD, Frey KM, Garforth SJ, Prasad VR, Schinazi RF, Liotta DC, Anderson KS (2012)
Pre-steady state kinetic analysis of cyclobutyl derivatives of 2'-deoxyadenosine 5'-triphosphate as inhibitors of HIV-1 reverse transcriptase.
Bioorganic & medicinal chemistry letters 22, 4064-4067 [PubMed:22595174]
[show Abstract]

Sato A, Cory JG (1981)
Evaluation of combinations of drugs that inhibit Ehrlich tumor cell ribonucleotide reductase.
Cancer research 41, 1637-1641 [PubMed:6783298]
[show Abstract]

Last Modified

27 July 2021

CHEBI:16284 - dATP

Key points

Abstract

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