MiMeDB: Showing metabocard for Fructose 1,6-bisphosphate (MMDBc0029539)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:31:31 UTC

Update Date

2022-08-31 13:42:52 UTC

MiMeDB ID

MMDBc0029539

Metabolite Identification

Common Name

Fructose 1,6-bisphosphate

Description

The hydrolysis of fructose 1,6-bisphosphate is catalized by Fructose-1,6-bisphosphatase (fru-1,6-P2ase, EC 3.1.3.11) to fructose 6-phosphate and inorganic phosphate and provides a mechanism to permit the reversal of the glycolysis reaction (catalyzed by 6-phosphofructo-1-kinase).(OMIM)

Structure

MOL SDF PDB SMILES InChI

Untitled Document-2
  Mrv0541 03121315212D          

 20 20  0  0  0  0            999 V2000
   -0.5690   -0.1311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0841   -0.7985    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7005   -0.5436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7005    0.2814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0841    0.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940   -0.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    1.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -1.0285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390   -1.5831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565    1.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315    0.5834    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315    1.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4565    0.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1921    1.8750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    2.2106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    2.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255    0.2814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  0  0  0  0
  1  6  1  1  0  0  0
  4  7  1  1  0  0  0
  3  8  1  1  0  0  0
  2  9  1  6  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
  4 20  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029539

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1

> <INCHI_KEY>
RNBGYGVWRKECFJ-ZXXMMSQZSA-N

> <FORMULA>
C6H14O12P2

> <MOLECULAR_WEIGHT>
340.1157

> <EXACT_MASS>
339.996048936

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
25.28187234820296

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.51

> <JCHEM_LOGP>
-3.0051313806666666

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.4935700215596843

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8894221949103747

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686727898823656

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
58.10659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fructose 1,6-bisphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-MAR-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-2                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-MAR-13         0                                  
HETATM    1  C   UNK     0      -1.062  -0.245   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.157  -1.491   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.308  -1.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.308   0.525   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.157   1.001   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.602  -0.245   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.934   1.932   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.554  -1.920   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.633  -2.955   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.372   1.089   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.465   2.093   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0      -4.912   1.089   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0      -4.912   2.629   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -4.912  -0.451   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.452   1.089   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       4.092   3.500   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0       5.499   2.874   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.685   4.126   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.718   4.907   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.848   0.525   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7   20                                             
CONECT    5    4    1                                                       
CONECT    6    1   10                                                       
CONECT    7    4   11                                                       
CONECT    8    3                                                            
CONECT    9    2                                                            
CONECT   10    6   12                                                       
CONECT   11    7   16                                                       
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   11   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20    4                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Synonyms

Value	Source
1,6-Di-O-phosphono-alpha-D-fructofuranose	ChEBI
ALPHA FRUCTOSE 1,6-diphosphATE	ChEBI
1,6-Di-O-phosphono-a-D-fructofuranose	Generator
1,6-Di-O-phosphono-α-D-fructofuranose	Generator
a FRUCTOSE 1,6-diphosphate	Generator
a FRUCTOSE 1,6-diphosphoric acid	Generator
alpha FRUCTOSE 1,6-diphosphoric acid	Generator
Α fructose 1,6-diphosphate	Generator
Α fructose 1,6-diphosphoric acid	Generator
Fructose 1,6-bisphosphoric acid	Generator
D-Fructose 1,6-biphosphate	HMDB
D-Fructose 1,6-bis(dihydrogen phosphate)	HMDB
D-Fructose 1,6-bisphosphate	HMDB
D-Fructose 1,6-diphosphate	HMDB
D-Fructose-1,6-bisphosphate	HMDB
D-Fructose-1,6-diphosphate	HMDB
Diphosphofructose	HMDB
Esafosfan	HMDB
Esafosfina	HMDB
FDP	HMDB
Fosfructose	HMDB
Fructose 1,6-bis	HMDB
Fructose 1,6-diphosphate	HMDB, MeSH, MeSH, MeSH, MeSH, MeSH, MeSH, MeSH
Harden-young ester	HMDB
SR-FDP	MeSH, HMDB
Fructose-1,6-diphosphate, (alpha-D)-isomer	MeSH, HMDB
Fructose-1,6-diphosphate, calcium (1:2) salt	MeSH, HMDB
Fructose-1,6-diphosphate, sodium salt, monohydrate	MeSH, HMDB
Strontium fructose 1,6-diphosphate	MeSH, HMDB
Fructose-1,6-diphosphate	MeSH, HMDB
Fructose-1,6-diphosphate magnesium salt	MeSH, HMDB
Fructose-1,6-diphosphate, (beta-D)-isomer	MeSH, HMDB
Fructose-1,6-diphosphate, disodium salt	MeSH, HMDB
Fructose-1,6-diphosphate, calcium salt	MeSH, HMDB
Fructose-1,6-diphosphate, tetrapotassium salt	MeSH, HMDB
Fructose-1,6-diphosphate, trisodium salt	MeSH, HMDB
Fructose-1,6-diphosphate, (L)-isomer	MeSH, HMDB
Fructose-1,6-diphosphate, 2-(18)O-labeled	MeSH, HMDB
Fructose-1,6-diphosphate, barium (1:2) salt	MeSH, HMDB
Fructose-1,6-diphosphate, monosodium salt	MeSH, HMDB
Fructose-1,6-diphosphate, tetrasodium salt	MeSH, HMDB
Strontium fructose-1,6-diphosphate	MeSH, HMDB

Chemical Formula

C₆H₁₄O₁₂P₂

Average Molecular Weight

340.1157

Monoisotopic Molecular Weight

339.996048936

IUPAC Name

{[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

fructose 1,6-bisphosphate

CAS Registry Number

488-69-7

SMILES

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

InChI Identifier

InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1

InChI Key

RNBGYGVWRKECFJ-ZXXMMSQZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Hexose phosphate
Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Tetrahydrofuran
1,2-diol
Hemiacetal
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose 1,6-bisphosphate (CHEBI:40595 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	16.1 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	58.11 m³·mol⁻¹	ChemAxon
Polarizability	25.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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
GC-MS	GC-MS Spectrum - GC-MS (7 TMS)	splash10-014i-0497100000-d0c0dfadfe65ee3cc4e5	2018-05-25	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)	splash10-014r-1779100000-ba60994aacef73cf8691	2018-05-25	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)	splash10-014r-0779100000-b52ccd042ce4169961ed	2018-05-25	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01xt-9532000000-c3c4929a4987e34c0dc0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-001j-6912320000-0890d12bae0d8fbc407e	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-9478000000-de8f4c9951e05a805014	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006y-8294000000-9a250122af91078d8ce6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9500000000-9efa8c4b7e69f8629450	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-7309000000-327ba0c662139f8a4418	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-baafdac5532e51e852cb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fa8d1793d2f2ff3e5105	2017-09-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	174	Human Feces; Human ; Pig	Unknown; Metabolic reconstruction
	Firmicutes	369	Human Feces; Human ; Pig ; Cattle	Metabolic reconstruction
	Bacteroidetes	116	Human Feces; Human	Metabolic reconstruction
	Actinobacteria	119	Human ; Human Feces	Metabolic reconstruction
	Fusobacteria	19	Human Feces; Human	Metabolic reconstruction
	Tenericutes	4	Human Feces	Metabolic reconstruction
	Synergistetes	3	Human Feces	Metabolic reconstruction
	Spirochaetes	1	Human Feces	Metabolic reconstruction
	Euryarchaeota	5	Human Feces; Human ; Cattle	Metabolic reconstruction
	Verrucomicrobia	1	Human	Metabolic reconstruction
	Thaumarchaeota	1	Human Feces	Metabolic reconstruction
	Planctomycetes	1	Human Feces	Metabolic reconstruction
	Crenarchaeota	1	Human Feces	Metabolic reconstruction
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB		details

External Links

HMDB ID

HMDB0060444

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fructose 1,6-bisphosphate

METLIN ID

Not Available

PubChem Compound

445557

PDB ID

Not Available

ChEBI ID

40595

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for Fructose 1,6-bisphosphate (MMDBc0029539)

MOL for #<Metabolite:0x00007f4598226f70>

3D MOL for #<Metabolite:0x00007f4598226f70>

3D SDF for #<Metabolite:0x00007f4598226f70>

3D-SDF for #<Metabolite:0x00007f4598226f70>

PDB for #<Metabolite:0x00007f4598226f70>

3D PDB for #<Metabolite:0x00007f4598226f70>

SMILES for #<Metabolite:0x00007f4598226f70>

INCHI for #<Metabolite:0x00007f4598226f70>

Structure for #<Metabolite:0x00007f4598226f70>

3D Structure for #<Metabolite:0x00007f4598226f70>