Milk Composition Database: Showing metabocard for Glycerol 3-phosphate (BMDB0000126)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:54 UTC

Update Date

2020-06-04 20:50:19 UTC

MCDB ID

BMDB0000126

Secondary Accession Numbers

BMDB00126

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 SDF 3D-SDF PDB SMILES InChI View 3D Structure

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
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-Glycerophosphate	HMDB
alpha-Glycerophosphorate	HMDB
alpha-Glycerophosphoric acid	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 1-phosphate	HMDB
Glycerol a-phosphate	HMDB
Glycerol monophosphate	HMDB
Glycerophosphorate	HMDB
Glycerophosphoric acid I	HMDB
Glyceryl phosphate	HMDB
sn-Glycerol 3-phosphate	HMDB
1-Phosphoglycerol	HMDB
alpha-Glycerophosphoric acid, (DL)-isomer	HMDB
alpha-Glycerophosphoric acid, (R)-isomer	HMDB
alpha-Glycerophosphoric acid, (S)-isomer	HMDB
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled	HMDB
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeled	HMDB
alpha-Glycerophosphoric acid, fe salt	HMDB
alpha-Glycerophosphoric acid, fe(+3) salt (3:2)	HMDB
alpha-Glycerophosphoric acid, calcium salt	HMDB
alpha-Glycerophosphoric acid, disodium salt	HMDB
alpha-Glycerophosphoric acid, disodium salt (+-)-isomer	HMDB
alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomer	HMDB
alpha-Glycerophosphoric acid, monocalcium salt	HMDB
alpha-Glycerophosphoric acid, monocalcium salt (S)-isomer	HMDB
alpha-Glycerophosphoric acid, monomagnesium salt	HMDB
alpha-Glycerophosphoric acid, sodium salt	HMDB
Disodium glycerophosphate	HMDB
Sodium glycerophosphate	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 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uea-0932000000-726f422c76a193edf232	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uea-0932000000-726f422c76a193edf232	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0zgj-1976000000-019de1fa6314b95ef7fe	2018-05-25	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-9300000000-a435ec7fb966f8ddc1a2	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0230-9080000000-9f48133c7a08fb549acd	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-9200000000-bf06c1d1e56cb8853243	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-9200000000-ffce45222cab00a0c302	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001j-9000000000-7689cca8f9c9a12d9e75	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0902000000-00e3a7e1ee10fbd8b03e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-1a40c90fd2eb656ddf5c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-9000000000-f9bc5f552db38767c437	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-72f8b96355726dd3a5b1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0901000000-2c3a8ed438d7ca0fa049	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-a3549fb5ec2675fbf615	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-9000000000-096e2ba9a6ef6fd20d88	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0930000000-171708905bad289d6031	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0925110000-c1ced10d34f533b3fa1f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-4ee8a36492a451beda75	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-9000000000-de2aacfb81476c7755e5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-dd342482ade09e9ce749	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0fkc-0917520000-d61e6034525ac5f7588d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-9000000000-d537d3f23f3d9a789c20	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-2f1ca45b50402f6e62df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0009000000-5606781224d6ab5caed3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0pi0-1900000000-75b6ed57a4c9cd6378b4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a59-6900000000-1c46fbda1468f6fd803c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a5c-9400000000-305e9a2554d8c3274f32	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-007o-9000000000-d11ad04a048c3dca25de	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00mo-9000000000-7b779b4be184b5b26b6a	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-5900000000-297dbde751110233eca5	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	80 uM	PMID: 11132867	details
Detected and Quantified	97 uM	PMID: 11132867	details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details

External Links

HMDB ID

HMDB0000126

DrugBank ID

DB02515

Phenol Explorer Compound ID

Not Available

FoodDB 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

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

Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. [PubMed:11132867 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.

Showing metabocard for Glycerol 3-phosphate (BMDB0000126)

Structure for BMDB0000126 (Glycerol 3-phosphate)