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{{distinguish|glycerol 3-phosphate|glycerate 3-phosphate}}
{{chembox
{{Chembox
| verifiedrevid = 443838247
|Verifiedfields = changed
| ImageFile = G3P-2D-skeletal.png
|Watchedfields = changed
| ImageSize = 180px
|verifiedrevid = 470454981
| ImageFile2 = D-Glyceraldehyde-3-phosphate-3D-balls.png
|ImageFile = D-Glycerinaldehyde 3-phosphate deprotonated V1.svg
| ImageSize2 = 180px
|ImageSize = 180px
|IUPACName=2-hydroxy-3-oxopropyl dihydrogen phosphate
|ImageClass = skin-invert
|OtherNames=
|ImageSize2 = 180px
|Section1= {{Chembox Identifiers
|IUPACName = 2-hydroxy-3-oxopropyl dihydrogen phosphate
| KEGG_Ref = {{keggcite|correct|kegg}}
|Section1={{Chembox Identifiers
| KEGG = C00661
|KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
|KEGG = C00661
| InChIKey = LXJXRIRHZLFYRP-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |KEGG1_Ref = {{keggcite|correct|kegg}}
|KEGG1 = C00118
| StdInChI = 1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
|InChI = 1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LXJXRIRHZLFYRP-UHFFFAOYSA-N |InChIKey = LXJXRIRHZLFYRP-UHFFFAOYAH
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| CASNo=142-10-9
|StdInChI = 1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
| PubChem=729
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = LXJXRIRHZLFYRP-UHFFFAOYSA-N
| ChemSpiderID = 709
|CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID1_Comment = (Racemic)
|CASNo = 591-59-3
| ChemSpiderID1 = 393755
|UNII = 7466PL1110
| ChemSpiderID1_Comment = (L isomer)
|UNII_Ref = {{fdacite|correct|FDA}}
| ChemSpiderID2 = 388314
|PubChem = 729
| ChemSpiderID2_Comment = (D isomer)
| ChEBI_Ref = {{ebicite|correct|EBI}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 709
| ChEBI = 17138
|ChemSpiderID_Comment = (Racemic)
| SMILES = O=P(O)(O)OCC(O)C=O
|ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| MeSHName=Glyceraldehyde+3-Phosphate
|ChemSpiderID1 = 393755
}}
|ChemSpiderID1_Comment = (L isomer)
|Section2= {{Chembox Properties
|ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| Formula=C<sub>3</sub>H<sub>7</sub>O<sub>6</sub>P
|ChemSpiderID2 = 388314
| MolarMass=170.058
|ChemSpiderID2_Comment = (D isomer)
| Appearance=
|ChEBI_Ref = {{ebicite|correct|EBI}}
| Density=
|ChEBI = 17138
| MeltingPt=
|ChEMBL = 1232918
| BoilingPt=
|DrugBank = DB02263
| Solubility=
|Beilstein = 1725008
}}
|EINECS = 209-721-7
|Section3= {{Chembox Hazards
|SMILES = C((C=O)O)OP(=O)(O)O
| MainHazards=
|MeSHName = Glyceraldehyde+3-Phosphate
| FlashPt=
| Autoignition=
}}
}} }}
|Section2={{Chembox Properties
'''Glyceraldehyde 3-phosphate''', also known as '''triose phosphate''' or '''3-phosphoglyceraldehyde''' and abbreviated as '''G3P''', '''GADP''', '''GAP''', '''TP''', '''GALP''' or '''PGAL''', is a ] that occurs as an intermediate in several central ]s of all organisms. It is a ] of the 3-carbon sugar ] and has ] ]<sub>3</sub>]<sub>7</sub>]<sub>6</sub>].
|Formula = C<sub>3</sub>H<sub>7</sub>O<sub>6</sub>P

|MolarMass = 170.058
The ] of glyceraldehyde 3-phosphate is 142-10-9 and that of D-glyceraldehyde 3-phosphate (one of the two ] of the compound and the one most often occurring in living organisms) is 591-57-1.
|MeltingPt = 102–104 °C<ref name="hmdb">{{cite web | title=metabocard for Glycerol 3-phosphate | url=http://www.hmdb.ca/metabolites/HMDB0000126}}</ref>
}}
}}
'''Glyceraldehyde 3-phosphate''', also known as '''triose phosphate''' or '''3-phosphoglyceraldehyde''' and abbreviated as '''G3P''', '''GA3P''', '''GADP''', '''GAP''', '''TP''', '''GALP''' or '''PGAL''', is a ] that occurs as an intermediate in several central ] of all organisms.<ref>{{cite book |last=Berg |first=Jeremy M. |author2=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=] |location=New York |isbn=0-7167-3051-0 |url=https://archive.org/details/biochemistrychap00jere |url-access=registration }}</ref><ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref> With the ] H(O)CCH(OH)CH<sub>2</sub>OPO<sub>3</sub><sup><sup>2-</sup></sup>, this anion is a ] of ].


==An intermediate in both glycolysis and gluconeogenesis== ==An intermediate in both glycolysis and gluconeogenesis==
===Formation=== ===Formation===
D-glyceraldehyde 3-phosphate is formed from the following three compounds in reversible reactions: D-glyceraldehyde 3-phosphate is formed from the following three compounds in reversible reactions:
* '''Fructose-1,6-bisphosphate (]), catalyzed by ].'''

{{Complex enzymatic reaction
*'''Fructose-1,6-bisphosphate (]), catalyzed by ].'''
| major_substrate_1 = β-<small>D</small>-]
{{ Complex Enzymatic Reaction
| major_substrate_1_stoichiometric_constant =
|major_substrate_1=β-<small>D</small>-]
| major_substrate_1_image = beta-D-fructose-1,6-bisphosphate_wpmp.png
|major_substrate_1_stoichiometric_constant=
| major_substrate_2 =
|major_substrate_1_image=beta-D-fructose-1,6-bisphosphate_wpmp.png
| major_substrate_2_stoichiometric_constant =
|major_substrate_2=
| major_substrate_2_image =
|major_substrate_2_stoichiometric_constant=
| major_product_1 = <small>D</small>-glyceraldehyde 3-phosphate
|major_substrate_2_image=
| major_product_1_stoichiometric_constant =
|major_product_1=<small>D</small>-glyceraldehyde 3-phosphate
| major_product_1_image = D-glyceraldehyde-3-phosphate_wpmp.png
|major_product_1_stoichiometric_constant=
| major_product_2 = ]
|major_product_1_image=D-glyceraldehyde-3-phosphate_wpmp.png
| major_product_2_stoichiometric_constant =
|major_product_2=]
| major_product_2_image = glycerone-phosphate_wpmp.png
|major_product_2_stoichiometric_constant=
| forward_enzyme = ]
|major_product_2_image=glycerone-phosphate_wpmp.png
|foward_enzyme=] | reverse_enzyme = ]
| reaction_direction_(forward/reversible/reverse)=reversible
|reverse_enzyme=]
| minor_forward_substrate(s)=
|reaction_direction_(foward/reversible/reverse)=reversible
| minor_forward_product(s)=
|minor_foward_substrate(s)=
| minor_reverse_product(s)=
|minor_foward_product(s)=
| minor_reverse_substrate(s)=
|minor_reverse_product(s)=
|minor_reverse_substrate(s)=
}} }}
{{KEGG compound|C05378}} {{KEGG enzyme|4.1.2.13}} {{KEGG compound|C00111}} {{KEGG compound|C00118}} {{KEGG compound|C05378}} {{KEGG enzyme|4.1.2.13}} {{KEGG compound|C00111}} {{KEGG compound|C00118}}


''The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.'' ''The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.''
* '''Dihydroxyacetone phosphate (]), catalyzed by ].'''

*'''Dihydroxyacetone phosphate (]), catalyzed by ].'''
{{Enzymatic Reaction {{Enzymatic Reaction
|foward_enzyme=] | forward_enzyme = ]
|reverse_enzyme=] | reverse_enzyme = ]
|substrate=] | substrate = ]
|product=<small>D</small>-glyceraldehyde 3-phosphate | product = <small>D</small>-glyceraldehyde 3-phosphate
|reaction_direction_(foward/reversible/reverse)=reversible | reaction_direction_(forward/reversible/reverse)=reversible
| minor_forward_substrate(s)=
|minor_foward_substrate(s)=
| minor_forward_product(s)=
|minor_foward_product(s)=
|minor_reverse_substrate(s)= | minor_reverse_substrate(s)=
|minor_reverse_product(s)= | minor_reverse_product(s)=
|substrate_image=glycerone-phosphate_wpmp.png | substrate_image = glycerone-phosphate_wpmp.png
|product_image=D-glyceraldehyde-3-phosphate_wpmp.png | product_image = D-glyceraldehyde-3-phosphate_wpmp.png
}} }}
{{KEGG compound|C00111}}{{KEGG enzyme|5.3.1.1}}{{KEGG compound|C00118}} {{KEGG compound|C00111}}{{KEGG enzyme|5.3.1.1}}{{KEGG compound|C00118}}
* '''1,3-bisphosphoglycerate (]), catalyzed by ].'''

*'''1,3-bisphosphoglycerate (]), catalyzed by ].'''


===As a substrate=== ===As a substrate===
*'''To produce ] in ].''' * '''To produce ] in ].'''
{{Enzymatic Reaction {{Enzymatic Reaction
|foward_enzyme=] | forward_enzyme = ]
|reverse_enzyme= | reverse_enzyme =
|substrate=glyceraldehyde 3-phosphate | substrate = glyceraldehyde 3-phosphate
|product=<small>D</small>-] | product = <small>D</small>-]
|reaction_direction_(foward/reversible/reverse)=reversible | reaction_direction_(forward/reversible/reverse)=reversible
|minor_foward_substrate(s)=NAD<sup>+</sup> '''+''' P<sub>i</sub> | minor_forward_substrate(s)=NAD<sup>+</sup> '''+''' P<sub>i</sub>
|minor_foward_product(s)=NADH '''+''' H<sup>+</sup> | minor_forward_product(s)=NADH '''+''' H<sup>+</sup>
|minor_reverse_substrate(s)=NADH '''+''' H<sup>+</sup> | minor_reverse_substrate(s)=NADH '''+''' H<sup>+</sup>
|minor_reverse_product(s)=NAD<sup>+</sup> '''+''' P<sub>i</sub> | minor_reverse_product(s)=NAD<sup>+</sup> '''+''' P<sub>i</sub>
|substrate_image=D-glyceraldehyde-3-phosphate_wpmp.png | substrate_image = D-glyceraldehyde-3-phosphate_wpmp.png
|product_image=1,3-bisphospho-D-glycerate_wpmp.png | product_image = 1,3-bisphospho-D-glycerate.svg
| product_image_size = 88px
}} }}
{{KEGG compound|C00118}} {{KEGG enzyme|1.2.1.12}} {{KEGG reaction|R01063}} {{KEGG compound|C00236}} {{KEGG compound|C00118}} {{KEGG enzyme|1.2.1.12}} {{KEGG reaction|R01063}} {{KEGG compound|C00236}}


D-glyceraldehyde 3-phosphate is also of some importance since this is how ] (as DHAP) enters the glycolytic and gluconeogenetic pathways. Furthermore, it is a participant in and a product of the ]. D-glyceraldehyde 3-phosphate is also of some importance since this is how ] (as DHAP) enters the glycolytic and gluconeogenic pathways. Furthermore, it is a participant in and a product of the ].

=== Interactive pathway map ===
|{{GlycolysisGluconeogenesis_WP534|highlight=Glyceraldehyde_3-phosphate}}


==An intermediate in photosynthesis== ==An intermediate in photosynthesis==
During plant ], 2 molecules of ] (GP; also known as 3-phosphoglycerate) are produced by the first step of the ]s when ] (RuBP) and ] are catalysed by the ] enzyme. The GP is converted to D-glyceraldehyde 3-phosphate (G3P) using the energy in ] and the reducing power of ] as part of the ]. This returns ], phosphate ions Pi, and ]+ to the ]s of photosynthesis for their continued function. During plant ], 2 equivalents of ] (GP; also known as 3-phosphoglycerate) are produced by the first step of the ]s when ] (RuBP) and ] are catalysed by the ] enzyme. The GP is converted to D-glyceraldehyde 3-phosphate (G3P) using the energy in ] and the reducing power of ] as part of the ]. This returns ], phosphate ions Pi, and ]+ to the ]s of photosynthesis for their continued function.
RuBP is regenerated for the Calvin cycle to continue. RuBP is regenerated for the Calvin cycle to continue.


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==In tryptophan biosynthesis== ==In tryptophan biosynthesis==
Glyceraldehyde 3-phosphate occurs as a byproduct in the biosynthesis pathway of ], an essential ] that cannot be produced by the human body. Glyceraldehyde 3-phosphate occurs as a byproduct in the biosynthesis pathway of ], an essential ] that cannot be produced by the human body.


==In thiamine biosynthesis== ==In thiamine biosynthesis==
Glyceraldehyde 3-phosphate occurs as a reactant in the biosynthesis pathway of ] (Vitamin B<sub>1</sub>), another substance that cannot be produced by the human body. Glyceraldehyde 3-phosphate occurs as a reactant in the biosynthesis pathway of ] (Vitamin B<sub>1</sub>), another substance that cannot be produced by the human body.

== References ==
{{reflist}}


== External links == == External links ==
{{Commonscat}}
* , from the ] * , from the ]
* , from the KEGG PATHWAY Database * , from the KEGG PATHWAY Database
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