MiMeDB: Showing metabocard for Sedoheptulose 7-phosphate (MMDBc0033115)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:35:24 UTC

Update Date

2024-04-20 06:15:16 UTC

Metabolite ID

MMDBc0033115

Metabolite Identification

Common Name

Sedoheptulose 7-phosphate

Description

D-Sedoheptulose 7-phosphate (CAS: 2646-35-7) is an intermediate of the pentose phosphate pathway (PPP) that has two functions: (1) the generation of NADPH for reductive syntheses and oxidative stress responses within cells, and (2) the formation of ribose residues for nucleotide and nucleic acid biosynthesis (PMID: 16055050 ). It is formed by transketolase and acted upon (degraded) by transaldolase. Sedoheptulose 7-phosphate can be increased in the blood of patients affected with a transaldolase deficiency, a genetic disorder (PMID: 12881455 ). Sedoheptulose is a ketoheptose, a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature (Wikipedia ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222352D          

 18 17  0  0  1  0            999 V2000
   10.3872   -9.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3872   -8.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6727   -9.4379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1016   -9.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1016  -10.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9582   -9.0254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6727  -10.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9582   -8.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2437   -9.4379    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5292   -9.0254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2437  -10.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -8.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8147   -9.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1003   -9.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3858   -9.4378    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -9.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857  -10.2628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1787   -8.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  1  0  0  0
  6  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  6  0  0  0
 10 12  1  1  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033115

> <DATABASE_NAME>
MIME

> <SMILES>
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H15O10P/c8-1-3(9)5(11)7(13)6(12)4(10)2-17-18(14,15)16/h4-8,10-13H,1-2H2,(H2,14,15,16)/t4-,5-,6-,7+/m1/s1

> <INCHI_KEY>
JDTUMPKOJBQPKX-GBNDHIKLSA-N

> <FORMULA>
C7H15O10P

> <MOLECULAR_WEIGHT>
290.1618

> <EXACT_MASS>
290.040283212

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
23.605812909365284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5S)-2,3,4,5,7-pentahydroxy-6-oxoheptyl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-4.020932865333332

> <ALOGPS_LOGS>
-1.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.517266191155728

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4919085850931326

> <JCHEM_PKA_STRONGEST_BASIC>
-3.327632992890398

> <JCHEM_POLAR_SURFACE_AREA>
184.98

> <JCHEM_REFRACTIVITY>
54.3972

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sedoheptulose-7-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.389 -16.847   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      19.389 -15.307   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      18.056 -17.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.723 -17.617   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      20.723 -19.157   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      16.722 -16.847   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.056 -19.157   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.722 -15.307   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.388 -17.617   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.055 -16.847   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.388 -19.157   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      14.055 -15.307   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.721 -17.617   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.387 -16.847   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0      10.053 -17.617   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0       8.720 -16.847   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.053 -19.157   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.667 -16.124   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1    6    7                                                  
CONECT    4    1    5                                                       
CONECT    5    4                                                            
CONECT    6    3    8    9                                                  
CONECT    7    3                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

Synonyms

Value	Source
Altro-heptulose 7-phosphate	ChEBI
D-Altro-heptulose 7-phosphate	ChEBI
D-Sedoheptulose 7-phosphate	ChEBI
Altro-heptulose 7-phosphoric acid	Generator
D-Altro-heptulose 7-phosphoric acid	Generator
D-Sedoheptulose 7-phosphoric acid	Generator
Sedoheptulose 7-phosphoric acid	Generator
Heptulose-7-phosphate	MeSH

Molecular Formula

C₇H₁₅O₁₀P

Average Mass

290.1618

Monoisotopic Mass

290.040283212

IUPAC Name

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

Traditional Name

sedoheptulose-7-phosphate

CAS Registry Number

2646-35-7

SMILES

OCC(=O)[C@@H](O)[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C7H15O10P/c8-1-3(9)5(11)7(13)6(12)4(10)2-17-18(14,15)16/h4-8,10-13H,1-2H2,(H2,14,15,16)/t4-,5-,6-,7+/m1/s1

InChI Key

JDTUMPKOJBQPKX-GBNDHIKLSA-N

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

ketoheptose phosphate (CHEBI:15721 )
sedoheptulose derivative (CHEBI:15721 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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	23.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05gj-7950000000-ec16725906be0353fe5c	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-3590000000-beb43376b75330818dfd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9710000000-da3e7cbb0d13e0a9852f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9300000000-bf280537f2111db2fa33	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-9730000000-95d5d8154dd52ae89762	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-013bf5e975401d875686	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ed1b1f0cc92369220eba	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cellular Cytoplasm
Fibroblasts
Placenta
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Saliva	HMDB	23857558
Frontotemporal dementia		Association	Human Saliva	HMDB	23857558
Transaldolase deficiency	Increased	Association	Human Blood	HMDB	12881455

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected and Quantified	0.91	0.26	uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Saliva	Detected and Quantified	0.84	0.13	uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Saliva	Detected and Quantified	1.60	1.55	uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Blood	Detected and Quantified	5.19	0.84	uM	Adult (>18 years old)	Both	Transaldolase deficiency	HMDB	12881455
Human Cellular cytoplasm	Detected and Quantified	74.9		uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Blood	Detected and Quantified	0.89	0.41	uM	Adult (>18 years old)	Both	Normal	HMDB	12881455
Human Saliva	Detected and Quantified	1.15	0.44	uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Blood	Detected and Quantified	1.15	0.66	uM	Children (1-13 years old)	Both	Normal	HMDB	12881455
Human Saliva	Detected and Quantified	0.299	0.236	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.360	1.20	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00019575

Chemspider ID

Not Available

KEGG Compound ID

C05382

BioCyc ID

D-SEDOHEPTULOSE-7-P

BiGG ID

Not Available

Wikipedia Link

Sedoheptulose_7-phosphate

METLIN ID

Not Available

PubChem Compound

165007

PDB ID

Not Available

ChEBI ID

15721

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Makarov SA, Kudriavtseva GV, Kolotilova AI: [Effect of prostaglandins F2 and F2 alpha on the pentosephosate pathway in human blood platelets]. Vopr Med Khim. 1983 Sep-Oct;29(5):27-32. [PubMed:6316661 ]
Thornalley PJ, Jahan I, Ng R: Suppression of the accumulation of triosephosphates and increased formation of methylglyoxal in human red blood cells during hyperglycaemia by thiamine in vitro. J Biochem. 2001 Apr;129(4):543-9. doi: 10.1093/oxfordjournals.jbchem.a002889. [PubMed:11275553 ]
Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. doi: 10.1373/49.8.1375. [PubMed:12881455 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. doi: 10.1016/j.jchromb.2005.01.001. Epub 2005 Jan 23. [PubMed:16055050 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Sedoheptulose 7-phosphate (MMDBc0033115)

MOL for #<Metabolite:0x00007fd12dc33218>

3D MOL for #<Metabolite:0x00007fd12dc33218>

3D SDF for #<Metabolite:0x00007fd12dc33218>

3D-SDF for #<Metabolite:0x00007fd12dc33218>

PDB for #<Metabolite:0x00007fd12dc33218>

3D PDB for #<Metabolite:0x00007fd12dc33218>

SMILES for #<Metabolite:0x00007fd12dc33218>

INCHI for #<Metabolite:0x00007fd12dc33218>

Structure for #<Metabolite:0x00007fd12dc33218>

3D Structure for #<Metabolite:0x00007fd12dc33218>