Sucrose (YMDB00906)

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Identification

YMDB ID

YMDB00906

Name

Sucrose

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Sucrose, also known as cane sugar or saccharose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Sucrose is an extremely weak basic (essentially neutral) compound (based on its pKa). Sucrose exists in all living species, ranging from bacteria to humans. sucrose can be converted into β-D-fructofuranose and α-D-glucose; which is catalyzed by the enzyme invertase. In yeast, sucrose is involved in the metabolic pathway called the fructose metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-Sucrose
b -D-Fructofuranosyl a-D-glucopyranoside
D-(+)-Saccharose
D-(+)-Sucrose
D-Sucrose
Saccharose
Saccharum
Sucrose
Sugar
Table sugar
White sugar
1-alpha-D-Glucopyranosyl-2-beta-D-fructofuranoside
beta-D-Fruf-(21)-alpha-D-GLCP
Cane sugar
Sacarosa
Sacharose
White soft sugar
Sugar, compressible
Sugar, confectioner's
Sugar spheres
Sucrose, purified
1-a-D-Glucopyranosyl-2-b-D-fructofuranoside
1-Α-D-glucopyranosyl-2-β-D-fructofuranoside
b-D-Fruf-(21)-a-D-GLCP
Β-D-fruf-(21)-α-D-GLCP

CAS number

57-50-1

Weight

Average: 342.2965
Monoisotopic: 342.116211546

InChI Key

CZMRCDWAGMRECN-UGDNZRGBSA-N

InChI

InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional IUPAC Name

sucrose

Chemical Formula

C₁₂H₂₂O₁₁

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@](O[C@@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
C-glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glycosyl glycoside (CHEBI:17992 )
Disaccharides (C00089 )

Physical Properties

State

Solid

Charge

Melting point

185.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	2100 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-3.70 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	824 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-4.5	ChemAxon
logS	0.38	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.77 m³·mol⁻¹	ChemAxon
Polarizability	31.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Fructose Metabolism	PW002390
Starch and sucrose metabolism	PW002481

KEGG Pathways

Galactose metabolism	ec00052
Starch and sucrose metabolism	ec00500

SMPDB Reactions

Sucrose + water → D-Fructose + Alpha-D-Glucose

Alpha-D-Glucose + D-Fructose ← Sucrose + water

KEGG Reactions

water + Sucrose D-Fructose + D-Glucose

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-0gba-0930000000-594ae5d59d217235e6c7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-02ta-0932000000-8fa2c23f886fb0c63312	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-00di-9731000000-0d702b863a0419bd559c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-0930000000-594ae5d59d217235e6c7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02ta-0932000000-8fa2c23f886fb0c63312	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9731000000-0d702b863a0419bd559c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0i01-0932000000-a84ab9868385a177391a	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nt9-9576000000-4af9cf7cb58154231f7b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-014i-8750249000-757f1c653f998599ba0b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-1ba130720abffe5e93d0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-002r-9600000000-bf4df12e3ec24b4de57b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9100000000-5308faa0508d0796ef2c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0fdx-9804000000-018a029ba3843a8db2bd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fdx-9804000000-018a029ba3843a8db2bd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9500000000-292e67f588f0d531ef65	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-2709000000-0e3c703e04384a1e3293	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-ef17557045affea2bd08	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-20fcddbd8c975ed3b6de	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0040-0591000000-7087bb9a939bd10f818a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000j-8900000000-9332c87e291ba54d3cbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-7744e4ab4fd78c24407f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0b9o-9404000000-1d981db61b2f46503e23	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-3920000000-4cba5c16114c58b38f7a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0v5a-7890000000-69957548042f63c9dd84	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4390000000-0d6a0896805d60fa3f2c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9300000000-a1b937218ce647359fdf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-6907000000-2f97793cff75b6ba35a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-9100000000-eb237dfae067794baf48	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-61fdb02b67338e94c2a3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-3b225ec11ada7061156b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9700000000-18b83ffd2452e8f7420d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-1901000000-b27bed8dffbc1fa29601	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fs-0900000000-85fe4d893cc72a297745	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-8900000000-7ee1d127314574cf8eec	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-05dm-9100000000-ff1c60103a4253a94cf7	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Fukushima, E., Arata, Y., Endo, T., Sonnewald, U., Sato, F. (2001). "Improved salt tolerance of transgenic tobacco expressing apoplastic yeast-derived invertase." Plant Cell Physiol 42:245-249.11230581
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Fitremann, Juliette; Queneau, Yves; Maitre, Jean-Paul; Bouchu, Alain. Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Letters (2007), 48(23), 4111-4114.

External Links:

Resource	Link
CHEBI ID	17992
HMDB ID	HMDB00258
Pubchem Compound ID	5988
Kegg ID	C00089
ChemSpider ID	24607894
FOODB ID	FDB003715
Wikipedia	Sucrose
BioCyc ID	SUCROSE

Enzymes

Protein Details

1. Glucosidase 2 subunit alpha

General function:: Involved in catalytic activity
Specific function:: Catalytic subunit of glucosidase 2, which cleaves sequentially the 2 innermost alpha-1,3-linked glucose residues from the Glc(2)Man(9)GlcNAc(2) oligosaccharide precursor of immature glycoproteins
Gene Name:: ROT2
Uniprot ID:: P38138
Molecular weight:: 110265.0

Reactions

Protein Details

2. Invertase 1

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC1
Uniprot ID:: P10594
Molecular weight:: 60569.89844

Protein Details

3. Invertase 3

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC3
Uniprot ID:: P10595
Molecular weight:: 8649.90039

Protein Details

4. Invertase 4

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC4
Uniprot ID:: P10596
Molecular weight:: 60574.80078

Protein Details

5. Invertase 5

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC5
Uniprot ID:: P10597
Molecular weight:: 8649.90039

Protein Details

6. Invertase 2

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC2
Uniprot ID:: P00724
Molecular weight:: 60638.89844

Reactions

Protein Details

7. Invertase 7

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC7
Uniprot ID:: P07635
Molecular weight:: 11248.90039

Structure for #<Compound:0xab0cf584>

Enzymes

Reactions

Reactions