P. aeruginosa Metabolome Database: Maltotriose (PAMDB000315)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000315

Identification

Name:

Maltotriose

Description:

Maltotriose is a member of the chemical class known as Trihexoses. These are trisaccharides containing three hexose carbohydrates. In Pseudomonas aeruginosa, maltotriose is an intermediate involved in degradation of glycogen to glucose. (Ecocyc)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

4-O-(4-O-Hexopyranosylhexopyranosyl)hexose
Amylotriose
D-(+)-Maltotriose
Delta-(+)-Maltotriose
Maltotriose
O-a-D-Glucopyranosyl-(1b94)-O-a-D-glucopyranosyl-(1b94)-O-a-D-glucose
O-a-delta-Glucopyranosyl-(1b94)-O-a-delta-glucopyranosyl-(1b94)-O-a-delta-glucose
O-a-δ-Glucopyranosyl-(1b94)-O-a-δ-glucopyranosyl-(1b94)-O-a-δ-glucose
O-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucose
O-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucose
O-α-D-Glucopyranosyl-(1β94)-O-α-D-glucopyranosyl-(1β94)-O-α-D-glucose
O-α-δ-Glucopyranosyl-(1β94)-O-α-δ-glucopyranosyl-(1β94)-O-α-δ-glucose
δ-(+)-Maltotriose

Chemical Formula:

C₁₈H₃₂O₁₆

Average Molecular Weight:

504.4371

Monoisotopic Molecular Weight:

504.169034976

InChI Key:

FYGDTMLNYKFZSV-DZOUCCHMSA-N

InChI:

InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1

CAS number:

1109-28-0

IUPAC Name:

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

Traditional IUPAC Name:

maltotriose

SMILES:

OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Oligosaccharides

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Secondary alcohol
Polyol
Hemiacetal
1,2-diol
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-8.004	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	554.0 mg/mL	ALOGPS
logP	-2.7	ALOGPS
logP	-6.5	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	268.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.75 m³·mol^-1	ChemAxon
Polarizability	46.65 Å³	ChemAxon
Number of Rings	3	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:

Cytoplasm

Reactions:

Adenosine triphosphate + Water + Maltotriose > ADP + Hydrogen ion + Maltotriose + Phosphate
Adenosine triphosphate + Water + Maltotriose > ADP + Hydrogen ion + Maltotriose + Phosphate
Water + Maltotetraose > D-Glucose + Maltotriose
D-Maltose + Maltotriose > D-Glucose + Maltotetraose
Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose
Maltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphate
Maltotriose + Water > D-Maltose + D-Glucose
-->-->Maltotetraose + Phosphate > Maltotriose + Alpha-D-glucose 1-phosphate
Maltotriose + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + Maltotriose + ADP
Maltotriose + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + Maltotriose + ADP

Pathways:

Porphyrin and chlorophyll metabolism pae00860
Starch and sucrose metabolism pae00500

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS)	splash10-0uxr-0961000000-eedb43ec0d980ce3b6dc	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS)	splash10-0uxr-0961000000-f2a522371c62148c925c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0uxr-0972000000-ea64ef22a740ff6d7271	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0udj-0972000000-4b10e9ea754fa393dc86	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS; 1 MEOX)	splash10-0fk9-9871000000-3de822f1f079a12db963	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS; 1 MEOX)	splash10-0fk9-9872000000-b2e2130ce45ac4ccf4ae	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0309000000-4045fdf8a9069c4881c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03ds-4900000000-f4d71bfee642eb6d42d4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9300000000-1c2e73b0b7042f4defba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0ir0-5911000000-c2aba069e7ab6ddbefa6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0h90-5911000000-c6cda5cae8a5bd10ca18	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Lingstrom P, Birkhed D, Granfeldt Y, Bjorck I: pH measurements of human dental plaque after consumption of starchy foods using the microtouch and the sampling method. Caries Res. 1993;27(5):394-401. Pubmed: 8242677
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. Pubmed: 19212411
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yuge O, Morio M, Fukui T, Fujii K, Kikuchi H, Takahashi S: Maltotriose and maltotetraose excreted in urine following intravenous administration of maltose to human volunteers. Jpn J Surg. 1983 Jul;13(4):296-303. Pubmed: 6645121

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	27931
HMDB ID	HMDB01262
Pubchem Compound ID	439586
Kegg ID	C01835
ChemSpider ID	388669
Wikipedia ID	Not Available
BioCyc ID	MALTOTRIOSE
EcoCyc ID	MALTOTRIOSE

Enzymes

Protein Details

• Maltose/maltodextrin import ATP-binding protein MalK

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
Gene Name:: malK
Locus Tag:: PA2341
Molecular weight:: 40.2 kDa

Reactions

ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).

Transporters

Protein Details

• Maltose/maltodextrin import ATP-binding protein MalK

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
Gene Name:: malK
Locus Tag:: PA2341
Molecular weight:: 40.2 kDa

Reactions

ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).

Maltotriose (PAMDB000315)

Structure for Maltotriose (PAMDB000315)

Enzymes

Reactions

Transporters

Reactions