thiamine(1+) diphosphate(1-) (CHEBI:45931)

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CHEBI:45931 - thiamine(1+) diphosphate(1−)

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ChEBI Name	thiamine(1+) diphosphate(1−)

ChEBI ID	CHEBI:45931

ChEBI ASCII Name	thiamine(1+) diphosphate(1-)

Definition	An ammonium betaine that is the conjugate base of thiamine(1+) diphosphate arising from the deprotonation of one of the hydroxy groups of the terminal phosphate group.

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

Secondary ChEBI IDs	CHEBI:45930, CHEBI:49939, CHEBI:15229

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

TDP - Ideal conformer

Mrv1927 07192113493D

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Time for openFile( TDP - Ideal conformer

Mrv1927 07192113493D

44 45 0 0 0 0 999 V2000

5.7930 2.2780 0.1900 N 0 0 0 0 0 0 0 0 0 0 0 0

6.8390 1.5610 0.5480 C 0 0 0 0 0 0 0 0 0 0 0 0

7.9430 2.2180 1.3360 C 0 0 0 0 0 0 0 0 0 0 0 0

6.9500 0.2870 0.2300 N 0 0 0 0 0 0 0 0 0 0 0 0

5.9920 -0.3260 -0.4600 C 0 0 0 0 0 0 0 0 0 0 0 0

6.1100 -1.6670 -0.7870 N 0 0 0 0 0 0 0 0 0 0 0 0

4.8700 0.4050 -0.8540 C 0 0 0 0 0 0 0 0 0 0 0 0

4.8000 1.7390 -0.5030 C 0 0 0 0 0 0 0 0 0 0 0 0

3.7630 -0.2450 -1.6430 C 0 0 1 0 0 0 0 0 0 0 0 0

2.8290 -0.9010 -0.7240 N 0 3 0 0 0 4 0 0 0 0 0 0

2.9880 -2.1750 -0.4490 C 0 0 0 0 0 0 0 0 0 0 0 0

1.6770 -2.4790 0.6490 S 0 0 0 0 0 0 0 0 0 0 0 0

0.9950 -0.8270 0.6570 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8530 -0.1990 -0.1880 C 0 0 0 0 0 0 0 0 0 0 0 0

1.6850 1.2630 -0.5120 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1970 -0.2810 1.3990 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.4520 -0.4420 0.5390 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.5820 0.0760 1.2430 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.8600 -0.1240 0.2840 P 0 0 2 0 0 5 0 0 0 0 0 0

-5.1510 0.5570 0.9610 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.1310 -1.6970 0.0730 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.5970 0.5110 -1.0270 O 0 0 0 0 0 0 0 0 0 0 0 0

-6.2710 0.6780 -0.1900 P 0 0 1 0 0 5 0 0 0 0 0 0

-7.7020 0.9780 0.4840 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.9010 1.8320 -1.1480 O 0 5 0 0 0 1 0 0 0 0 0 0

-6.3410 -0.6470 -0.9810 O 0 0 0 0 0 0 0 0 0 0 0 0

7.7350 2.1220 2.4020 H 0 0 0 0 0 0 0 0 0 0 0 0

8.8920 1.7340 1.1050 H 0 0 0 0 0 0 0 0 0 0 0 0

8.0000 3.2740 1.0710 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4090 -2.1050 -1.2940 H 0 0 0 0 0 0 0 0 0 0 0 0

6.8930 -2.1670 -0.5090 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9470 2.3360 -0.7910 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2330 0.5140 -2.2180 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1860 -0.9860 -2.3210 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7400 -2.8590 -0.8130 H 0 0 0 0 0 0 0 0 0 0 0 0

2.3250 1.8550 0.1420 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9650 1.4390 -1.5500 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6450 1.5510 -0.3610 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3250 -0.8280 2.3340 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0380 0.7750 1.6160 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3240 0.1050 -0.3950 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6110 -1.4980 0.3220 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 8 1 0 0 0 0

2 3 1 0 0 0 0

2 4 1 0 0 0 0

3 27 1 0 0 0 0

3 28 1 0 0 0 0

3 29 1 0 0 0 0

4 5 2 0 0 0 0

5 6 1 0 0 0 0

5 7 1 0 0 0 0

6 30 1 0 0 0 0

6 31 1 0 0 0 0

7 8 2 0 0 0 0

7 9 1 0 0 0 0

8 32 1 0 0 0 0

9 10 1 0 0 0 0

9 33 1 0 0 0 0

9 34 1 0 0 0 0

10 11 2 0 0 0 0

10 14 1 0 0 0 0

11 12 1 0 0 0 0

11 35 1 0 0 0 0

12 13 1 0 0 0 0

13 14 2 0 0 0 0

13 16 1 0 0 0 0

14 15 1 0 0 0 0

15 36 1 0 0 0 0

15 37 1 0 0 0 0

15 38 1 0 0 0 0

16 17 1 0 0 0 0

16 39 1 0 0 0 0

16 40 1 0 0 0 0

17 18 1 0 0 0 0

17 41 1 0 0 0 0

17 42 1 0 0 0 0

19 18 1 6 0 0 0

19 20 1 0 0 0 0

19 21 2 0 0 0 0

19 22 1 0 0 0 0

20 23 1 0 0 0 0

22 43 1 0 0 0 0

23 24 2 0 0 0 0

23 25 1 6 0 0 0

23 26 1 0 0 0 0

26 44 1 0 0 0 0

M CHG 2 10 1 25 -1

M END): 19 ms

reading 44 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

44 atoms created

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

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Formula

C12H18N4O7P2S

Net Charge

Average Mass

424.300

Monoisotopic Mass

424.03714

InChI

InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)

InChIKey

AYEKOFBPNLCAJY-UHFFFAOYSA-N

SMILES

CC1=C(CCOP(O)(=O)OP(O)([O-])=O)SC=[N+]1CC1=C(N)N=C(C)N=C1

Metabolite of Species	Details
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via B vitamin )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	thiamine(1+) diphosphate(1−) (CHEBI:45931) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) thiamine(1+) diphosphate(1−) (CHEBI:45931) has role human metabolite (CHEBI:77746) thiamine(1+) diphosphate(1−) (CHEBI:45931) is a ammonium betaine (CHEBI:35284) thiamine(1+) diphosphate(1−) (CHEBI:45931) is a thiamine phosphate (CHEBI:26945) thiamine(1+) diphosphate(1−) (CHEBI:45931) is a vitamin B₁ (CHEBI:26948) thiamine(1+) diphosphate(1−) (CHEBI:45931) is conjugate acid of thiamine(1+) diphosphate(3−) (CHEBI:58937) thiamine(1+) diphosphate(1−) (CHEBI:45931) is conjugate base of thiamine(1+) diphosphate (CHEBI:9532)

Incoming	thiamine(1+) diphosphate (CHEBI:9532) is conjugate acid of thiamine(1+) diphosphate(1−) (CHEBI:45931) thiamine(1+) diphosphate(3−) (CHEBI:58937) is conjugate base of thiamine(1+) diphosphate(1−) (CHEBI:45931)

IUPAC Name

2-{3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl}ethyl dihydrogen diphosphate

Synonyms	Sources
thiamin diphosphate	PDBeChem
thiamin pyrophosphate	ChemIDplus
thiamine diphosphate	ChEBI
thiamine pyrophosphate	ChemIDplus

Manual Xref	Database
TDP	PDBeChem
View more database links

Registry Numbers	Types	Sources
136-09-4	CAS Registry Number	ChemIDplus
4168438	Beilstein Registry Number	Beilstein

Citations

Sabui S, Romero JM, Said HM (2021)
Developmental maturation of the colonic uptake process of the microbiota-generated thiamin pyrophosphate.
American journal of physiology. Gastrointestinal and liver physiology 320, G829-G835 [PubMed:33759569]
[show Abstract]

Du X, Cheng X, Li W, Ge Z, Zhong C, Fan C, Gu H (2021)
Engineering Allosteric Ribozymes to Detect Thiamine Pyrophosphate in Whole Blood.
Analytical chemistry 93, 4277-4284 [PubMed:33635634]
[show Abstract]

Nauton L, Hecquet L, Théry V (2021)
QM/MM Study of Human Transketolase: Thiamine Diphosphate Activation Mechanism and Complete Catalytic Cycle.
Journal of chemical information and modeling 61, 3502-3515 [PubMed:34161071]
[show Abstract]

Ma J, Saikia N, Godar S, Hamilton GL, Ding F, Alper J, Sanabria H (2021)
Ensemble Switching Unveils a Kinetic Rheostat Mechanism of the Eukaryotic Thiamine Pyrophosphate Riboswitch.
RNA (New York, N.Y.)rna.075937.120 [PubMed:33863818]
[show Abstract]

Ucak T, Karakurt Y, Tasli G, Cimen FK, Icel E, Kurt N, Ahiskali I, Süleyman H (2019)
The effects of thiamine pyrophosphate on ethanol induced optic nerve damage.
BMC pharmacology & toxicology 20, 40 [PubMed:31277705]
[show Abstract]

Background

We aimed to determine the protective effects of thiamine pyrophosphate on ethanol induced optic neuropathy in an experimental model.

Methods

The rats were assigned into 4 groups, with 6 rats in each group as follows: healthy controls (HC group), only ethanol administered group (EtOH group), ethanol + thiamine pyrophosphate (20 mg/kg) administered group (TEt-20 group), and only thiamine pyrophosphate (20 mg/kg) (TPG group) administered group. To the rats in TEt-20 and TPG groups, 20 mg/kg thiamine pyrophosphate was administered via intraperitoneal route. To the rats in HC and EtOH groups, the same volume (0.5 ml) of distilled water as solvent was applied in the same manner. To the rats in TEt-20 and EtOH groups, one hour after application of thiamine pyrophosphate or distilled water, 32% ethanol with a dose of 5 g/kg was administered via oral gavage. This procedure was repeated once a day for 6 weeks. From the blood samples and tissues obtained from the rats, Malondialdehyde (MDA), reduced glutathione (GSH), interleukin 1 beta (IL-1β) and tumor necrosis factor alpha (TNF-α) levels were studied. Histopathological evaluations were performed to the optic nerve tissue.

Results

Serum and tissue IL-1β, TNF-α and MDA levels were the highest in EtOH group which were significantly lower in thiamine pyrophosphate administered group (TEt-20 group) (p: 0.001). Serum and tissue reduced GSH levels were the lowest in EtOH group which were also significantly higher in TEt-20 group (p:0.001). In histopathological evaluations, in EtOH group there was obvious destruction and edema with hemorrhage and dilated blood vessels which were not present in any other groups.

Conclusions

There was an apparent destruction in ethanol administered group in histopathological analyses with an augmented level of oxidative stress markers and all those alterations were prevented with concomitant thiamine pyrophosphate administration. These protective effects of thiamine pyrophosphate are extremely important in chronic ethanol consumption. Clinical studies are warranted to define the exact role of thiamine pyrophosphate in prevention of ethanol induced optic neuropathy.

Rosado-Souza L, Proost S, Moulin M, Bergmann S, Bocobza SE, Aharoni A, Fitzpatrick TB, Mutwil M, Fernie AR, Obata T (2019)
Appropriate Thiamin Pyrophosphate Levels Are Required for Acclimation to Changes in Photoperiod.
Plant physiology 180, 185-197 [PubMed:30837347]
[show Abstract]

Last Modified

19 July 2021

CHEBI:45931 - thiamine(1+) diphosphate(1−)

Background

Methods

Results

Conclusions

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