MiMeDB: Showing metabocard for D-fructose 1,6-bisphosphate (MMDBc0033086)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:34:09 UTC

Update Date

2024-04-20 06:11:57 UTC

Metabolite ID

MMDBc0033086

Metabolite Identification

Common Name

D-fructose 1,6-bisphosphate

Description

Fructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate fructose. The enzyme aldolase splits fructose 1,6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.

Structure

MOL SDF PDB SMILES InChI

ChEBI
  Mrv0541 02241222322D          

 23 22  0  0  1  0            999 V2000
   14.7400   -5.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7400   -6.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7400   -7.3818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7400   -8.2068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.7400   -9.0318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.7400   -9.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4545  -10.2693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4545   -5.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5650   -6.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9150   -7.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5650   -7.3818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9150   -8.2068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5650   -8.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9150   -9.0318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5650   -9.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2874   -5.3271    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.0809   -5.3428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2795   -6.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2795   -4.4943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5073  -10.2536    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.2459  -10.2536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4994   -9.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4994  -10.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  1  1  0  0  0
  3 11  1  1  0  0  0
  4 12  1  1  0  0  0
  4 13  1  1  0  0  0
  5 14  1  1  0  0  0
  5 15  1  1  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 16  1  0  0  0  0
  8 16  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23 20  1  0  0  0  0
  7 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033086

> <DATABASE_NAME>
MIME

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

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

> <INCHI_KEY>
XPYBSIWDXQFNMH-UYFOZJQFSA-N

> <FORMULA>
C6H14O12P2

> <MOLECULAR_WEIGHT>
340.1157

> <EXACT_MASS>
339.996048936

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
25.525007836038164

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-1.61

> <JCHEM_LOGP>
-3.514163954666666

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.6633055259475853

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.006253866577405

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5447528314482835

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
59.3076

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-fructose 1,6-bisphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      27.515 -10.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.515 -12.239   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.515 -13.779   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.515 -15.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.515 -16.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.515 -18.399   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      28.848 -19.169   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      28.848  -9.929   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.055 -12.239   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      25.975 -13.779   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0      29.055 -13.779   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0      25.975 -15.319   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      29.055 -15.319   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      25.975 -16.859   0.000  0.00  0.00           H+0
HETATM   15  O   UNK     0      29.055 -16.859   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0      30.403  -9.944   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0      31.884  -9.973   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      30.388 -11.499   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      30.388  -8.389   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      30.814 -19.140   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      32.192 -19.140   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      30.799 -17.585   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      30.799 -20.387   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4   10   11                                             
CONECT    4    3    5   12   13                                             
CONECT    5    4    6   14   15                                             
CONECT    6    5    7                                                       
CONECT    7    6   20                                                       
CONECT    8    1   16                                                       
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    4                                                            
CONECT   14    5                                                            
CONECT   15    5                                                            
CONECT   16   17   18   19    8                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   21   22   23    7                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

Synonyms

Value	Source
1,6-Di-O-phosphono-D-fructose	ChEBI
D-Fructose 1,6-bisphosphate	ChEBI
D-Fructose-1,6-diphosphate	ChEBI
Fructose-1,6-diphosphate	ChEBI
Harden-young ester	ChEBI
D-Fructose 1,6-bisphosphoric acid	Generator
D-Fructose-1,6-diphosphoric acid	Generator
Fructose-1,6-diphosphoric acid	Generator
Fructose-1,6-diphosphate, (alpha-D)-isomer	MeSH
Fructose-1,6-diphosphate, sodium salt, monohydrate	MeSH
Fructose-1,6-diphosphate, monosodium salt	MeSH
Fructose-1,6-diphosphate, calcium (1:2) salt	MeSH
Strontium fructose 1,6-diphosphate	MeSH
Fructose 1,6-diphosphate	MeSH
SR-FDP	MeSH
Fructose-1,6-diphosphate, disodium salt	MeSH
Fructose 1,6-bisphosphate	MeSH
Fructose-1,6-diphosphate, 2-(18)O-labeled	MeSH
Fructose-1,6-diphosphate, (L)-isomer	MeSH
Fructose-1,6-diphosphate, calcium salt	MeSH
Fructose-1,6-diphosphate, tetrapotassium salt	MeSH
Fructose-1,6-diphosphate, (beta-D)-isomer	MeSH
Strontium fructose-1,6-diphosphate	MeSH
Fructose-1,6-diphosphate, tetrasodium salt	MeSH
Fructose-1,6-diphosphate, trisodium salt	MeSH
Fructose-1,6-diphosphate, barium (1:2) salt	MeSH
Fructose-1,6-diphosphate magnesium salt	MeSH

Molecular Formula

C₆H₁₄O₁₂P₂

Average Mass

340.1157

Monoisotopic Mass

339.996048936

IUPAC Name

{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]oxy}phosphonic acid

Traditional Name

D-fructose 1,6-bisphosphate

CAS Registry Number

488-69-7

SMILES

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

InChI Identifier

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

InChI Key

XPYBSIWDXQFNMH-UYFOZJQFSA-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
Monosaccharide phosphate
Glycerone 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
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-fructose 1,6-bisphosphate (CHEBI:16905 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	13.6 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-3.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.01	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	59.31 m³·mol⁻¹	ChemAxon
Polarizability	25.53 Å³	ChemAxon
Number of Rings	0	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-EI-TOF (Non-derivatized)	splash10-00kb-0955000000-424463ed06df92a04093	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kk-1954000000-c578c6dc8f011032d008	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-8922000000-e52833b8a5a291a52187	2016-09-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0109000000-5374d73d3b6f0d1d67cc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0002-9100000000-90d958ebad119c7c60f4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00gl-0197000000-2c666d207be881c4ef28	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0kk9-0392000000-2e114e2ff3476fa48de6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-1960000000-d78713458d852ddd22e7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052b-5900000000-d65f29d5f722e387b3eb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-3b992f02b655d8e877c3	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1249000000-705e8e2d0bf1c8ef0552	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-4921000000-47a02a183df4faa521d5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9810000000-9d59b24daf1d7967e6e3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002k-5903000000-13d1be2828c65e407664	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-e78f4a266f65b4d059f2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f3dcf179be35cf051b41	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cellular Cytoplasm
Placenta

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

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

Exposure Sources

Other Exposures

Source Type	Activity	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cellular cytoplasm	Detected and Quantified	7.60		3.60	11.6	uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Blood	Detected and Quantified	1.2	0.4			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	3.8	0.7			uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

DB13863

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

FRUCTOSE-16-DIPHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

84951

PDB ID

Not Available

ChEBI ID

16905

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Norne JE, Lilja H, Lindman B, Einarsson R, Zeppezauer M: Pt(CN)2-4 and Au(CN)-2: potential general probes for anion-binding sites of proteins. 35Cl and 81Br nuclear-magnetic-resonance studies. Eur J Biochem. 1975 Nov 15;59(2):463-73. doi: 10.1111/j.1432-1033.1975.tb02475.x. [PubMed:1204623 ]
Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. doi: 10.1007/BF00710290. [PubMed:8412001 ]
Acan NL, Ozer N: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. J Enzyme Inhib. 2001 Nov;16(5):457-64. doi: 10.1080/14756360109162395. [PubMed:11916152 ]
Ahn SM, Yoon HY, Lee BG, Park KC, Chung JH, Moon CH, Lee SH: Fructose-1,6-diphosphate attenuates prostaglandin E2 production and cyclo-oxygenase-2 expression in UVB-irradiated HaCaT keratinocytes. Br J Pharmacol. 2002 Oct;137(4):497-503. doi: 10.1038/sj.bjp.0704896. [PubMed:12359631 ]
Riedel BJ, Gal J, Ellis G, Marangos PJ, Fox AW, Royston D: Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesth Analg. 2004 Jan;98(1):20-29. doi: 10.1213/01.ANE.0000094336.97693.90. [PubMed:14693576 ]
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 ]
Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
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Showing metabocard for D-fructose 1,6-bisphosphate (MMDBc0033086)

MOL for #<Metabolite:0x000055eee8d595d0>

3D MOL for #<Metabolite:0x000055eee8d595d0>

3D SDF for #<Metabolite:0x000055eee8d595d0>

3D-SDF for #<Metabolite:0x000055eee8d595d0>

PDB for #<Metabolite:0x000055eee8d595d0>

3D PDB for #<Metabolite:0x000055eee8d595d0>

SMILES for #<Metabolite:0x000055eee8d595d0>

INCHI for #<Metabolite:0x000055eee8d595d0>

Structure for #<Metabolite:0x000055eee8d595d0>

3D Structure for #<Metabolite:0x000055eee8d595d0>