Maltose (YMDB00584)

Identification

YMDB ID

YMDB00584

Name

Maltose

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Maltose, also known as alpha-malt sugar or cextromaltose, 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. D-Maltose is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Maltose exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-alpha-d-glucopyranosyl-4-alpha-d-glucopyranose
1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose
4-(alpha-D-glucopyranosido)-alpha-glucopyranose
4-(alpha-D-glucosido)-D-glucose
4-(alpha-delta-glucopyranosido)-alpha-glucopyranose
4-(alpha-delta-glucosido)-delta-glucose
4-O-a-D-Glucopyranosyl-D-glucose
4-O-alpha-D-glucopyranosyl-D-glucopyranose
4-O-alpha-D-glucopyranosyl-D-glucose
4-O-alpha-delta-glucopyranosyl-delta-glucopyranose
4-O-alpha-delta-glucopyranosyl-delta-glucose
4-O-Hexopyranosylhexose
alpha-D-Glcp-(1->4)-D-Glcp
alpha-D-glucopyranosyl-(1->4)-D-glucopyranose
alpha-D-glucopyranosyl-(1->4)-D-glucose
alpha-delta-Glcp-(1->4)-delta-Glcp
alpha-delta-glucopyranosyl-(1->4)-delta-glucopyranose
alpha-delta-glucopyranosyl-(1->4)-delta-glucose
alpha-Malt sugar
Cextromaltose
D-(+)-maltose
D-Maltose
delta-(+)-maltose
delta-Maltose
Finetose
Finetose F
Madoros
Madoros (TN)
malt sugar
Maltobiose
Maltodiose
Maltos
Maltose
Maltose (NF)
Maltose HH
Maltose HHH
Maltose solution
Malzzucker
Martos-10
Sunmalt
Sunmalt S
4-O-alpha-D-Glucopyranosyl-alpha-D-mannopyranose
4-O-a-D-Glucopyranosyl-a-D-mannopyranose
4-O-Α-D-glucopyranosyl-α-D-mannopyranose
Advantose 100

CAS number

69-79-4

Weight

Average: 342.2965
Monoisotopic: 342.116211546

InChI Key

GUBGYTABKSRVRQ-PICCSMPSSA-N

InChI

InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11?,12-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

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

Chemical Formula

C₁₂H₂₂O₁₁

SMILES

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

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

alpha-D-glucosyl-(1->4)-D-mannopyranose (CHEBI:47937 )

Physical Properties

State

Solid

Charge

Melting point

102-103 °C

Experimental Properties

Property	Value	Reference
Water Solubility	780 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	586 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	11.25	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	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	31.43 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

Flavour/Odour	Source
Odorless	FDB001193

SMPDB Pathways

Starch and sucrose metabolism

PW002481

KEGG Pathways

Starch and sucrose metabolism

ec00500

SMPDB Reactions

Maltose → Alpha-D-Glucose

KEGG Reactions

Maltose + water → D-Glucose

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-4897000000-332d470623cd7f1e1ced	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-014i-3421129000-03a98898fd3278f95502	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 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 ("D-Maltose,3TBDMS,#3" TMS) - 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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01ox-0149000000-74748828832d87932342	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-008c-2950000000-4ebee22b86c2cc9ee3ab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kg-9710000000-041dbc580f99b8881518	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03gl-0907000000-a1de7813fbe8b5258c10	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0900000000-79cc5059a3f338e8c1dd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3900000000-851d0bc84d91b6e09579	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0749000000-af1d18f2bc3ab8e02883	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0200-2902000000-67218697344afb9e70fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01td-4900000000-40aa2d8125769803cfbb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0109000000-9d0f9a68a67bafd734ab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01rw-3898000000-7f495a1bcfdbed6466c4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ti-9210000000-b8a83657f0266d372bee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-1069000000-9cd867711bca0eecf935	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9365000000-65403961bfb5e35eaa0d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9200000000-0de9785c1c5df1430dd2	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
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
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
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
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
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C 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
Serrano, R. (1977). "Energy requirements for maltose transport in yeast." Eur J Biochem 80:97-102.21792
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:

Pedersen, Sven; Vang Hendriksen, Hanne. Method for production of maltose and/or enzymatically modified starch. PCT Int. Appl. (2001), 99 pp.

External Links:

Resource	Link
CHEBI ID	17306
HMDB ID	HMDB00163
Pubchem Compound ID	439186
Kegg ID	C00208
ChemSpider ID	23327704
FOODB ID	FDB001193
Wikipedia	Maltose
BioCyc ID	MALTOSE

Enzymes

Protein Details

1. Alpha-glucosidase MAL32

General function:: Involved in catalytic activity
Specific function:: Hydrolysis of terminal, non-reducing (1->4)- linked alpha-D-glucose residues with release of alpha-D-glucose
Gene Name:: MAL32
Uniprot ID:: P38158
Molecular weight:: 68141.79688

Reactions

Protein Details

2. 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

3. Alpha-glucosidase MAL12

General function:: Involved in catalytic activity
Specific function:: Hydrolysis of terminal, non-reducing (1->4)- linked alpha-D-glucose residues with release of alpha-D-glucose
Gene Name:: MAL12
Uniprot ID:: P53341
Molecular weight:: 68093.70313

Reactions

Protein Details

4. Probable alpha-glucosidase YIL172C/YJL221C

General function:: Carbohydrate transport and metabolism
Specific function:: Probable alpha-glucosidase involved in maltose metabolism
Gene Name:: Not Available
Uniprot ID:: P40439
Molecular weight:: 68698.10156

Protein Details

5. Alpha-glucosidase MAL62

General function:: Involved in catalytic activity
Specific function:: Hydrolysis of terminal, non-reducing (1->4)- linked alpha-D-glucose residues with release of alpha-D-glucose
Gene Name:: MAL62
Uniprot ID:: P07265
Molecular weight:: 68182.79688

Protein Details

6. Oligo-1,6-glucosidase

General function:: Involved in catalytic activity
Specific function:: Preferentially hydrolyzes isomaltose, with little activity towards isomaltotriose or longer oligosaccharides. Does not hydrolyze maltose
Gene Name:: FSP2
Uniprot ID:: P53051
Molecular weight:: 68591.0

Reactions

Transporters

Protein Details

1. General alpha-glucoside permease

General function:: Involved in transmembrane transporter activity
Specific function:: High-affinity uptake of alpha-glucosides such as maltose, turanose, isomaltose, alpha-methylglucoside, maltotriose, palatinose, trehalose, melezitose and glucose. Acts with the concomitant transport of protons into the cell (symport system)
Gene Name:: MAL11
Uniprot ID:: P53048
Molecular weight:: 67979.60156

Protein Details

2. Maltose permease MAL31

General function:: Involved in transmembrane transporter activity
Specific function:: High-affinity uptake of maltose and maltotriose. Also transports turanose but not alpha-methylglucoside, melezitose or trehalose
Gene Name:: MAL31
Uniprot ID:: P38156
Molecular weight:: 68262.20313

Structure for #<Compound:0xae61e488>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters