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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (17) Show 17 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:32 UTC

HMDB ID

HMDB0000126

Secondary Accession Numbers

HMDB0002722
HMDB00126
HMDB02722

Metabolite Identification

Common Name

Glycerol 3-phosphate

Description

Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Glycerol 1-phosphate	ChEBI
D-(Glycerol 1-phosphate)	ChEBI
D-Glycerol 1-phosphate	ChEBI
Glycerol-3-phosphate	ChEBI
Glycerophosphoric acid	ChEBI
L-(Glycerol 3-phosphate)	ChEBI
Phosphoric acid mono-((R)-2,3-dihydroxy-propyl) ester	ChEBI
Phosphorsaeure-mono-((R)-2,3-dihydroxy-propylester)	ChEBI
sn-GLYCEROL-3-phosphATE	ChEBI
sn-Gro-1-p	ChEBI
(R)-Glycerol 1-phosphoric acid	Generator
D-(Glycerol 1-phosphoric acid)	Generator
D-Glycerol 1-phosphoric acid	Generator
Glycerol-3-phosphoric acid	Generator
Glycerophosphate	Generator
L-(Glycerol 3-phosphoric acid)	Generator
Phosphate mono-((R)-2,3-dihydroxy-propyl) ester	Generator
sn-GLYCEROL-3-phosphoric acid	Generator
Glycerol 3-phosphoric acid	Generator
Glycerolphosphates	MeSH
Glycerophosphate, calcium	MeSH
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled	MeSH
alpha-Glycerophosphoric acid, fe(+3) salt (3:2)	MeSH
alpha-Glycerophosphoric acid, disodium salt	MeSH
alpha-Glycerophosphoric acid, disodium salt (+-)-isomer	MeSH
Disodium glycerophosphate	MeSH
Glycerol 1-phosphate	MeSH
1-Phosphoglycerol	MeSH
alpha-Glycerophosphoric acid, (DL)-isomer	MeSH
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeled	MeSH
alpha-Glycerophosphoric acid, calcium salt	MeSH
Calcium glycerophosphate	MeSH
alpha-Glycerophosphoric acid	MeSH
alpha-Glycerophosphoric acid, fe salt	MeSH
alpha-Glycerophosphoric acid, monocalcium salt (S)-isomer	MeSH
alpha-Glycerophosphoric acid, monomagnesium salt	MeSH
alpha-Glycerophosphoric acid, sodium salt	MeSH
Glycerolphosphate	MeSH
Glycerophosphates	MeSH
alpha-Glycerophosphate	MeSH
alpha-Glycerophosphoric acid, (R)-isomer	MeSH
alpha-Glycerophosphoric acid, (S)-isomer	MeSH
alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomer	MeSH
alpha-Glycerophosphoric acid, monocalcium salt	MeSH
Sodium glycerophosphate	MeSH
1-(Dihydrogen phosphate) glycerol	HMDB
1-Glycerophosphate	HMDB
1-Glycerophosphorate	HMDB
1-Glycerophosphoric acid	HMDB
3-Glycerophosphate	HMDB
a-Glycerophosphate	HMDB
a-Glycerophosphorate	HMDB
a-Glycerophosphoric acid	HMDB
a-Phosphoglycerol	HMDB
alpha-Glycerophosphorate	HMDB
alpha-Phosphoglycerol	HMDB
Dihydrogen a-glycerophosphate	HMDB
DL-a-Glycerol phosphate	HMDB
DL-a-Glycerophosphate	HMDB
DL-a-Glycerophosphorate	HMDB
DL-a-Glycerophosphoric acid	HMDB
DL-a-Glyceryl phosphate	HMDB
DL-alpha-Glycerol phosphate	HMDB
DL-alpha-Glycerophosphate	HMDB
DL-alpha-Glycerophosphorate	HMDB
DL-alpha-Glycerophosphoric acid	HMDB
DL-alpha-Glyceryl phosphate	HMDB
DL-Glycerol 1-phosphate	HMDB
DL-Glycerol 3-phosphate	HMDB
Glycerol a-phosphate	HMDB
Glycerol monophosphate	HMDB
Glycerophosphorate	HMDB
Glycerophosphoric acid I	HMDB
Glyceryl phosphate	HMDB
sn-Glycerol 3-phosphate	HMDB

Chemical Formula

C₃H₉O₆P

Average Molecular Weight

172.0737

Monoisotopic Molecular Weight

172.013674532

IUPAC Name

[(2R)-2,3-dihydroxypropoxy]phosphonic acid

Traditional Name

3-phosphoglycerol

CAS Registry Number

57-03-4

SMILES

OC[C@@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1

InChI Key

AWUCVROLDVIAJX-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

Glycerophosphates

Alternative Parents

Substituents

Sn-glycerol-3-phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sn-glycerol 3-phosphates (CHEBI:15978 )
glycerol 1-phosphate (CHEBI:15978 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 - 104 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	124.856	30932474
[M-H]-	Not Available	127.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000179

Predicted Molecular Properties

Property	Value	Source
Water Solubility	30.6 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2	ChemAxon
logS	-0.75	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.39 m³·mol⁻¹	ChemAxon
Polarizability	13.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.399	31661259
DarkChem	[M-H]-	129.049	31661259
AllCCS	[M+H]+	138.361	32859911
AllCCS	[M-H]-	130.262	32859911
DeepCCS	[M+H]+	127.493	30932474
DeepCCS	[M-H]-	123.663	30932474
DeepCCS	[M-2H]-	161.151	30932474
DeepCCS	[M+Na]+	136.512	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.5	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.0	32859911
AllCCS	[M-H]-	130.3	32859911
AllCCS	[M+Na-2H]-	132.6	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.74 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0659 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.93 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	427.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	455.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	325.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	36.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	210.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	221.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	844.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	572.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	641.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	788.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	396.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	439.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycerol 3-phosphate	OC[C@@H](O)COP(O)(O)=O	2871.2	Standard polar	33892256
Glycerol 3-phosphate	OC[C@@H](O)COP(O)(O)=O	1606.0	Standard non polar	33892256
Glycerol 3-phosphate	OC[C@@H](O)COP(O)(O)=O	1614.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycerol 3-phosphate,1TMS,isomer #1	C[Si](C)(C)OC[C@@H](O)COP(=O)(O)O	1628.7	Semi standard non polar	33892256
Glycerol 3-phosphate,1TMS,isomer #2	C[Si](C)(C)O[C@H](CO)COP(=O)(O)O	1630.4	Semi standard non polar	33892256
Glycerol 3-phosphate,1TMS,isomer #3	C[Si](C)(C)OP(=O)(O)OC[C@H](O)CO	1640.1	Semi standard non polar	33892256
Glycerol 3-phosphate,2TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C	1673.1	Semi standard non polar	33892256
Glycerol 3-phosphate,2TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C	1691.0	Semi standard non polar	33892256
Glycerol 3-phosphate,2TMS,isomer #3	C[Si](C)(C)O[C@H](CO)COP(=O)(O)O[Si](C)(C)C	1682.6	Semi standard non polar	33892256
Glycerol 3-phosphate,2TMS,isomer #4	C[Si](C)(C)OP(=O)(OC[C@H](O)CO)O[Si](C)(C)C	1672.8	Semi standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	1734.7	Semi standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	1704.1	Standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	2010.1	Standard polar	33892256
Glycerol 3-phosphate,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1736.4	Semi standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1717.9	Standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1824.9	Standard polar	33892256
Glycerol 3-phosphate,3TMS,isomer #3	C[Si](C)(C)O[C@H](CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1720.9	Semi standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #3	C[Si](C)(C)O[C@H](CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1715.0	Standard non polar	33892256
Glycerol 3-phosphate,3TMS,isomer #3	C[Si](C)(C)O[C@H](CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1848.4	Standard polar	33892256
Glycerol 3-phosphate,4TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1766.2	Semi standard non polar	33892256
Glycerol 3-phosphate,4TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1760.5	Standard non polar	33892256
Glycerol 3-phosphate,4TMS,isomer #1	C[Si](C)(C)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1791.0	Standard polar	33892256
Glycerol 3-phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)(O)O	1887.5	Semi standard non polar	33892256
Glycerol 3-phosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)(O)O	1878.0	Semi standard non polar	33892256
Glycerol 3-phosphate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H](O)CO	1881.4	Semi standard non polar	33892256
Glycerol 3-phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2093.4	Semi standard non polar	33892256
Glycerol 3-phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C	2108.2	Semi standard non polar	33892256
Glycerol 3-phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C	2104.8	Semi standard non polar	33892256
Glycerol 3-phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H](O)CO)O[Si](C)(C)C(C)(C)C	2121.2	Semi standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2364.3	Semi standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2314.5	Standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2319.8	Standard polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2348.5	Semi standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2301.2	Standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2187.0	Standard polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2346.5	Semi standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2284.6	Standard non polar	33892256
Glycerol 3-phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2191.4	Standard polar	33892256
Glycerol 3-phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2587.5	Semi standard non polar	33892256
Glycerol 3-phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2435.8	Standard non polar	33892256
Glycerol 3-phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2231.1	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Glycerol Phosphate Shuttle		Not Available
Oxidative phosphorylation	Not Available
Phospholipid Biosynthesis
Glycerolipid Metabolism
Glycerol Kinase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	30.0 +/- 3.0 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	6.33 +/- 3.24 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	5.30 +/- 2.20 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	13.48 +/- 7.10 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Saliva	Detected and Quantified	14.80 +/- 11.37 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected and Quantified	18.18 +/- 11.57 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	19.83 +/- 10.17 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Alzheimer's disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]

Associated OMIM IDs

114500 (Colorectal cancer)
104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)

External Links

DrugBank ID

DB02515

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15978

Food Biomarker Ontology

Not Available

VMH ID

GLYC3P

MarkerDB ID

MDB00000061

Good Scents ID

Not Available

References

Synthesis Reference

Rios-Mercadillo, Victor M.; Whitesides, George M. Enzymic synthesis of sn-glycerol 3-phosphate. Journal of the American Chemical Society (1979), 101(19), 5828-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Slomiany BL, Piotrowski J, Mojtahed H, Slomiany A: Ebrotidine effect on the proteolytic and lipolytic activities of Helicobacter pylori. Gen Pharmacol. 1992 Mar;23(2):203-6. [PubMed:1639232 ]
Guminski T: Some glycolytic enzymes in normal cerebrospinal fluid, brain tissue and blood plasma of infants. Clin Chim Acta. 1976 Aug 16;71(1):61-6. [PubMed:134854 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Glycerol-3-phosphate dehydrogenase, mitochondrial

General function:: Involved in calcium ion binding
Specific function:: Not Available
Gene Name:: GPD2
Uniprot ID:: P43304
Molecular weight:: 80851.99

Reactions

Glycerol 3-phosphate + a quinone → Dihydroxyacetone phosphate + a quinol	details
Glycerol 3-phosphate + FAD → Dihydroxyacetone phosphate + FADH	details

Enzyme Details

2. Glycerol kinase 2

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: Key enzyme in the regulation of glycerol uptake and metabolism (By similarity).
Gene Name:: GK2
Uniprot ID:: Q14410
Molecular weight:: 60593.32

Reactions

Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphate	details

Enzyme Details

3. Glycerol kinase

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: Key enzyme in the regulation of glycerol uptake and metabolism.
Gene Name:: GK
Uniprot ID:: P32189
Molecular weight:: 57488.675

Reactions

Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphate	details

Enzyme Details

4. Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: GPD1
Uniprot ID:: P21695
Molecular weight:: 37567.4

Reactions

Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH	details
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Ion	details

Enzyme Details

5. Glycerol-3-phosphate acyltransferase 1, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis.
Gene Name:: GPAM
Uniprot ID:: Q9HCL2
Molecular weight:: 93793.895

Reactions

Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphate	details
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier protein	details

Enzyme Details

6. Putative glycerol kinase 3

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: Key enzyme in the regulation of glycerol uptake and metabolism.
Gene Name:: GK3P
Uniprot ID:: Q14409
Molecular weight:: Not Available

Reactions

Adenosine triphosphate + Glycerol → ADP + Glycerol 3-phosphate	details

Enzyme Details

7. Glycerol-3-phosphate acyltransferase 4

General function:: Involved in acyltransferase activity
Specific function:: Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis. Active against both saturated and unsaturated long-chain fatty acyl-CoAs.
Gene Name:: AGPAT6
Uniprot ID:: Q86UL3
Molecular weight:: 52070.605

Reactions

Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphate	details
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier protein	details

Enzyme Details

8. CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase, mitochondrial

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin (By similarity).
Gene Name:: PGS1
Uniprot ID:: Q32NB8
Molecular weight:: 62729.745

Reactions

CDP-diacylglycerol + Glycerol 3-phosphate → Cytidine monophosphate + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate	details
CDP-diacylglycerol + Glycerol 3-phosphate → Cytidine monophosphate + Phosphatidylglycerophosphate	details

Enzyme Details

9. Glycerol-3-phosphate dehydrogenase 1-like protein

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in regulating cardiac sodium current; decreased enzymatic activity with resulting increased levels of glycerol 3-phosphate activating the DPD1L-dependent SCN5A phosphorylation pathway, may ultimately lead to decreased sodium current; cardiac sodium current may also be reduced due to alterations of NAD(H) balance induced by DPD1L.
Gene Name:: GPD1L
Uniprot ID:: Q8N335
Molecular weight:: 38418.44

Reactions

Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH	details
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Ion	details

Enzyme Details

10. Glycerol-3-phosphate acyltransferase 3

General function:: Involved in acyltransferase activity
Specific function:: Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis. Overexpression activates the mTOR pathway.
Gene Name:: AGPAT9
Uniprot ID:: Q53EU6
Molecular weight:: 48704.805

Reactions

Acyl-CoA + Glycerol 3-phosphate → Coenzyme A + 1-acyl-sn-glycerol 3-phosphate	details
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate → 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier protein	details

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Glycerol 3-phosphate (HMDB0000126)

MOL for HMDB0000126 (Glycerol 3-phosphate)

3D MOL for HMDB0000126 (Glycerol 3-phosphate)

3D SDF for HMDB0000126 (Glycerol 3-phosphate)

3D-SDF for HMDB0000126 (Glycerol 3-phosphate)

PDB for HMDB0000126 (Glycerol 3-phosphate)

3D PDB for HMDB0000126 (Glycerol 3-phosphate)

SMILES for HMDB0000126 (Glycerol 3-phosphate)

INCHI for HMDB0000126 (Glycerol 3-phosphate)

Structure for HMDB0000126 (Glycerol 3-phosphate)

3D Structure for HMDB0000126 (Glycerol 3-phosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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