Milk Composition Database: Showing metabocard for D-Glucose (BMDB0000122)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:49 UTC

Update Date

2020-06-04 21:34:49 UTC

MCDB ID

BMDB0000122

Secondary Accession Numbers

BMDB00122

Metabolite Identification

Common Name

D-Glucose

Description

D-Glucose, also known as D-GLC or cerelose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-Glucose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Glucose exists in all living species, ranging from bacteria to humans. In cattle, D-glucose is involved in the metabolic pathway called the starch and sucrose metabolism pathway. D-Glucose is a potentially toxic compound. D-Glucose has been found to be associated with several diseases known as hypoglycemia, familial neonatal, donohue syndrome, and pregnancy; also d-glucose has been linked to several inborn metabolic disorders including 3-methyl-crotonyl-glycinuria and growth hormone deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-GLC	ChEBI
D-GLCP	ChEBI
Dextrose	ChEBI
GLC-OH	ChEBI
Glucose	ChEBI
Grape sugar	ChEBI
WURCS=2.0/1,1,0/[a2122h-1x_1-5]/1/	ChEBI
Purified glucose	Kegg
D-Glucopyranose	Kegg
Roferose ST	HMDB
(+)-Glucose	HMDB
Anhydrous dextrose	HMDB, MeSH
Cerelose	HMDB
Cerelose 2001	HMDB
Clearsweet 95	HMDB
Clintose L	HMDB
Corn sugar	HMDB
CPC Hydrate	HMDB
D(+)-Glucose	HMDB
Dextropur	HMDB
Dextrosol	HMDB
Glucodin	HMDB
Glucolin	HMDB
Goldsugar	HMDB
Meritose	HMDB
Staleydex 111	HMDB
Staleydex 95m	HMDB
Tabfine 097(HS)	HMDB
Vadex	HMDB
D Glucose	MeSH, HMDB
Glucose, (DL)-isomer	MeSH, HMDB
Glucose, (L)-isomer	MeSH, HMDB
Glucose, (beta-D)-isomer	MeSH, HMDB
Glucose monohydrate	MeSH, HMDB
Glucose, (alpha-D)-isomer	MeSH, HMDB
L Glucose	MeSH, HMDB
L-Glucose	MeSH, HMDB
Dextrose, anhydrous	MeSH, HMDB
Monohydrate, glucose	MeSH, HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Traditional Name

glucose

CAS Registry Number

50-99-7

SMILES

[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1

InChI Key

WQZGKKKJIJFFOK-GASJEMHNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucopyranose (CHEBI:4167 )
D-glucose (CHEBI:4167 )
Aldoses (C00031 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	146 - 150 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1200 mg/mL	Not Available
LogP	-3.24	SANGSTER (1994)

Predicted Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.37 Å³	ChemAxon
Number of Rings	1	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 (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00kb-1931000000-ec21c3af97621f7bf95a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-0fr2-1920000000-f53c5f0d5ad84d32679f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)	splash10-00di-9821000000-dbc697213e3b7cc9d4fe	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)	splash10-00di-9621000000-9d1d8057758d3da8caca	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014i-2490000000-3ed4c4fd34c05bad95f7	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)	splash10-066r-1952000000-3378cb724e551e8b0267	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0udl-0690000000-c8fda4276ff69235f30d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)	splash10-0ldi-1942000000-5d531ed23a4e82023d1c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0udi-0790000000-7ebe75cd633c58d761fa	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-1931000000-ec21c3af97621f7bf95a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-1920000000-f53c5f0d5ad84d32679f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9821000000-dbc697213e3b7cc9d4fe	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-9d1d8057758d3da8caca	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-2490000000-3ed4c4fd34c05bad95f7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066r-1952000000-3378cb724e551e8b0267	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udl-0690000000-c8fda4276ff69235f30d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ldi-1942000000-5d531ed23a4e82023d1c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0790000000-7ebe75cd633c58d761fa	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0002-9300000000-839f41cf94a071fcdb37	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0002-9000000000-807f75d14f3d0b66f5bd	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000t-9000000000-b89668f86992a8363664	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-7900000000-9a673c2e4b82ca397421	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4r-9100000000-b70415588e768ddce5ef	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-73dc84dd88d8ae69fe02	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-a61efd1469735758b317	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-7900000000-9a673c2e4b82ca397421	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9100000000-9c25b149885d8a48aab5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-76d92ea96364c24ecfb0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a61efd1469735758b317	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-b0bc47623e7b2ca31c02	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-648e1637af29cf2a3518	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9200000000-9e6f46a1cbf52d6e347a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-a4ec4f0b1e29e360a952	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-ec2bf4918640a0a36398	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1900000000-6e953691e4c61d5123d9	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-9200000000-42768e14d42bd5ebe785	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08ov-9000000000-ee9eba654c17ccffa05f	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-9700000000-b92609de9f7db41f6d8f	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9100000000-31314220c313e7443171	2021-10-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-2a9c77b5036ec23fe0d4	2021-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, 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	376 uM	PMID: 2760296	details
Detected and Quantified	723 uM	PMID: 9891269	details
Detected and Quantified	540 uM	PMID: 11132867	details
Detected and Quantified	548 uM	PMID: 11132867	details
Detected and Quantified	1137 uM	PMID: 18336416	details
Detected and Quantified	1188 uM	PMID: 18336416	details
Detected and Quantified	76 - 662 uM	PMID: 20338431	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 25108860	details
Detected and Quantified	63 uM	PMID: 11913692	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	288 +/- 32 uM	PMID: 30994344	details
Detected and Quantified	261 +/- 29 uM	PMID: 30994344	details
Detected and Quantified	235 +/- 49 uM	PMID: 30994344	details
Detected and Quantified	250 +/- 41 uM	PMID: 30994344	details
Detected and Quantified	340 +/- 66 uM	PMID: 29642378	details
Detected and Quantified	387 +/- 91 uM	PMID: 29642378	details
Detected and Quantified	331 +/- 84 uM	PMID: 29642378	details
Detected and Quantified	277 (122-422) uM	Esperanza Troyano...	details
Detected and Quantified	80-150 uM	Faulkner, A., Cha...	details
Detected and Quantified	932 +/- 68 uM	RAJAN SHARMA YUDH...	details
Detected and Quantified	140 +/- 4 uM	Tommaso R.I. Cata...	details
Detected and Quantified	250 +/- 41 uM	PMID: 30994344	details
Detected and Quantified	288 +/- 32 uM	PMID: 30994344	details
Detected and Quantified	261 +/- 29 uM	PMID: 30994344	details
Detected and Quantified	235 +/- 49 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0304632

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glucose

METLIN ID

Not Available

PubChem Compound

5793

PDB ID

Not Available

ChEBI ID

4167

References

Synthesis Reference

Li, Dalin; Ruan, Yi; Song, Wen; Wang, Yongjun. Improved process for producing glucose. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 4 pp

Material Safety Data Sheet (MSDS)

Not Available

General References

Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. [PubMed:2760296 ]
Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6. [PubMed:9891269 ]
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 ]
Lehloenya KV, Stein DR, Allen DT, Selk GE, Jones DA, Aleman MM, Rehberger TG, Mertz KJ, Spicer LJ: Effects of feeding yeast and propionibacteria to dairy cows on milk yield and components, and reproduction*. J Anim Physiol Anim Nutr (Berl). 2008 Apr;92(2):190-202. doi: 10.1111/j.1439-0396.2007.00726.x. [PubMed:18336416 ]
Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
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.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for D-Glucose (BMDB0000122)

Structure for BMDB0000122 (D-Glucose)