ECMDB: D-Sedoheptulose 7-phosphate (ECMDB01068) (M2MDB000240)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)XML

Proteins (1576)

Record Information

Version

2.0

Creation Date

2012-05-31 13:44:28 -0600

Update Date

2015-09-17 15:41:08 -0600

Secondary Accession Numbers

ECMDB01068

Identification

Name:

D-Sedoheptulose 7-phosphate

Description

D-sedoheptulose 7-phosphate is a member of the chemical class known as Heptoses. These are monosaccharides in which the sugar unit is an heptose. D-sedoheptulose 7-phosphate is invovled in lipopolysaccharide biosynthesis, the pentose phosphate pathway (non-oxidative), the biosynthesis of secondary metabolites, the pentose phosphate pathway, and microbial metabolism in diverse environments. Sedoheptulose 7-phosphate is an intermediate in the pentose phosphate pathway. It is formed by transketolase and acted upon by transaldolase.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

7-(dihydrogen phosphate) sedoheptulose
7-(Dihydrogen phosphate) sedoheptulose (6ci,7ci,8ci)
7-(Dihydrogen phosphoric acid) sedoheptulose
7-(Dihydrogen phosphoric acid) sedoheptulose (6ci,7ci,8ci)
D-Altro-2-heptulose 7-(dihydrogen phosphate)
D-altro-2-Heptulose 7-(dihydrogen phosphoric acid)
D-Sedoheptulose 7-phosphoric acid
D-Sedoheptulose-7-p
D-Sedoheptulose-7-phosphate
D-Sedoheptulose-7-phosphoric acid
Heptulose 7-phosphate
Heptulose 7-phosphoric acid
Heptulose-7-phosphate
Heptulose-7-phosphoric acid
S7P
Sedo-heptulose-7-phosphate
sedo-Heptulose-7-phosphoric acid
Sedoheptulose 7-phosphate
Sedoheptulose 7-phosphoric acid
Sedoheptulose-7-p
Sedoheptulose-7-phosphate
Sedoheptulose-7-phosphoric acid

Chemical Formula:

C₇H₁₅O₁₀P

Weight:

Average: 290.1618
Monoisotopic: 290.040283212

InChI Key:

CBIDVWSRUUODHL-QTSLKERKSA-N

InChI:

InChI=1S/C7H15O10P/c8-2-7(12)6(11)5(10)4(9)3(17-7)1-16-18(13,14)15/h3-6,8-12H,1-2H2,(H2,13,14,15)/t3-,4-,5-,6+,7?/m1/s1

CAS number:

2646-35-7

IUPAC Name:

[(2,3,4,5,7-pentahydroxy-6-oxoheptyl)oxy]phosphonic acid

Traditional IUPAC Name:

sedoheptulose 7-phosphate

SMILES:

OCC1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Heptose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-4.657	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	25.1 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	184.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	54.4 m³·mol⁻¹	ChemAxon
Polarizability	23.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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:

SMPDB Pathways:

ADP-L-glycero-Beta-D-manno-heptose biosynthesis	PW002095
Lipopolysaccharide biosynthesis	PW000831
Pentose Phosphate	PW000893
Sedoheptulose Bisphosphate Bypass	PW002098

KEGG Pathways:

Biosynthesis of ansamycins ec01051
Carbon fixation in photosynthetic organisms ec00710
Lipopolysaccharide biosynthesis ec00540
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Pentose phosphate pathway ec00030

EcoCyc Pathways:

ADP-L-glycero-β-D-manno-heptose biosynthesis PWY0-1241
pentose phosphate pathway (non-oxidative branch) NONOXIPENT-PWY
sedoheptulose bisphosphate bypass PWY0-1517

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0532-9010163000-acf4f0352711d42c5fd6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-3590000000-b34117115db1142c20a4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4m-9710000000-f24eb76da4873de6d41f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9300000000-b8503ab37c97a6fff189	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-9730000000-02687371ce694d179c1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9200000000-27d52a9bf7e9b234f147	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4a6e471e293da809c157	View in MoNA

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
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15721
HMDB ID	HMDB01068
Pubchem Compound ID	616
Kegg ID	C05382
ChemSpider ID	596
Wikipedia	sedoheptulose 7-phosphate
BioCyc ID	D-SEDOHEPTULOSE-7-P
EcoCyc ID	D-SEDOHEPTULOSE-7-P

Enzymes

Protein Details

1. 6-phosphofructokinase isozyme 2

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:: pfkB
Uniprot ID:: P06999
Molecular weight:: 32456

Reactions

ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.

Protein Details

2. 6-phosphofructokinase isozyme 1

General function:: Involved in ATP binding
Specific function:: ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:: pfkA
Uniprot ID:: P0A796
Molecular weight:: 34842

Reactions

ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.

Protein Details

3. Transaldolase A

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:: talA
Uniprot ID:: P0A867
Molecular weight:: 35659

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate.

Protein Details

4. Transaldolase B

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:: talB
Uniprot ID:: P0A870
Molecular weight:: 35219

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate.

Protein Details

5. Transketolase 1

General function:: Involved in catalytic activity
Specific function:: Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:: tktA
Uniprot ID:: P27302
Molecular weight:: 72211

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.

Protein Details

6. Transketolase 2

General function:: Involved in catalytic activity
Specific function:: Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:: tktB
Uniprot ID:: P33570
Molecular weight:: 73042

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.

Protein Details

7. Phosphoheptose isomerase

General function:: Involved in D-sedoheptulose 7-phosphate isomerase activity
Specific function:: Catalyzes the isomerization of sedoheptulose 7-phosphate in D-glycero-D-manno-heptose 7-phosphate
Gene Name:: gmhA
Uniprot ID:: P63224
Molecular weight:: 20815

Reactions

D-sedoheptulose 7-phosphate = D-glycero-D-manno-heptose 7-phosphate.

D-Sedoheptulose 7-phosphate (ECMDB01068) (M2MDB000240)

Structure for #<Compound:0xae07d024>

Enzymes

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