D-Fructose 1,6-bisphosphate (CHEM035051)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:26:59 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035051
Identification
Common NameD-Fructose 1,6-bisphosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,6-Di-O-phosphono-beta-D-fructofuranoseChEBI
BETA FRUCTOSE 1,6-diphosphATEChEBI
beta-D-Fructose 1,6-bisphosphateChEBI
FosfructoseChEBI
1,6-Di-O-phosphono-b-D-fructofuranoseGenerator
1,6-Di-O-phosphono-β-D-fructofuranoseGenerator
b FRUCTOSE 1,6-diphosphateGenerator
b FRUCTOSE 1,6-diphosphoric acidGenerator
beta FRUCTOSE 1,6-diphosphoric acidGenerator
Β fructose 1,6-diphosphateGenerator
Β fructose 1,6-diphosphoric acidGenerator
b-D-Fructose 1,6-bisphosphateGenerator
b-D-Fructose 1,6-bisphosphoric acidGenerator
beta-D-Fructose 1,6-bisphosphoric acidGenerator
Β-D-fructose 1,6-bisphosphateGenerator
Β-D-fructose 1,6-bisphosphoric acidGenerator
Fructose 1,6-bisphosphoric acidGenerator
Fructose-1,6-diphosphateHMDB
Fructose-1,6-diphosphate, calcium saltHMDB
Fructose-1,6-diphosphate, disodium saltHMDB
Fructose-1,6-diphosphate, trisodium saltHMDB
Fructose-1,6-diphosphate, 2-(18)O-labeledHMDB
Fructose-1,6-diphosphate, calcium (1:2) saltHMDB
Fructose-1,6-diphosphate, monosodium saltHMDB
Strontium fructose 1,6-diphosphateHMDB
SR-FDPHMDB
Fructose 1,6-diphosphateHMDB
Fructose-1,6-diphosphate, (L)-isomerHMDB
Fructose-1,6-diphosphate, (alpha-D)-isomerHMDB
Fructose-1,6-diphosphate, barium (1:2) saltHMDB
Fructose-1,6-diphosphate, sodium salt, monohydrateHMDB
Fructose-1,6-diphosphate, tetrasodium saltHMDB
Strontium fructose-1,6-diphosphateHMDB
Fructose-1,6-diphosphate magnesium saltHMDB
Fructose-1,6-diphosphate, (beta-D)-isomerHMDB
Fructose-1,6-diphosphate, tetrapotassium saltHMDB
D-Fructose 1,6-biphosphateHMDB
D-Fructose 1,6-bisphosphateHMDB
D-Fructose 1,6-diphosphateHMDB
DiphosphofructoseHMDB
Fructose 1,6-bis(dihydrogen phosphate)HMDB
beta-D-Fructofuranose 1,6-bisphosphateHMDB
beta-D-Fructofuranose 1,6-diphosphateHMDB
beta-D-Fructose 1,6-diphosphateHMDB
Β-D-fructofuranose 1,6-bisphosphateHMDB
Β-D-fructofuranose 1,6-diphosphateHMDB
Β-D-fructose 1,6-diphosphateHMDB
Fructose 1,6-bisphosphateMeSH
b-D-Fructofuranose 1,6-bisphosphateGenerator
b-D-Fructofuranose 1,6-bisphosphoric acidGenerator
beta-D-Fructofuranose 1,6-bisphosphoric acidGenerator
Β-D-fructofuranose 1,6-bisphosphoric acidGenerator
Chemical FormulaC6H14O12P2
Average Molecular Mass340.116 g/mol
Monoisotopic Mass339.996 g/mol
CAS Registry Number488-69-7
IUPAC Name{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid
SMILESO[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
InChI IdentifierInChI=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 KeyRNBGYGVWRKECFJ-ARQDHWQXSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m³·mol⁻¹ChemAxon
Polarizability25.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-014i-0497100000-d0c0dfadfe65ee3cc4e5Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)splash10-014r-1779100000-ba60994aacef73cf8691Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)splash10-014r-0779100000-b52ccd042ce4169961edSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01xt-9532000000-c3c4929a4987e34c0dc0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03fs-9412510000-0a0a9e96cc6bea61e3c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0006-0190000000-95a4b5217606c0b9d1fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0002-0900000000-74a1700e0fae0f6aa64eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-0009000000-631b4fa683b46f4c89cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-1009000000-9df66c58adba653741e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000j-7129000000-f1414a0a896a7c132d2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-0002-9111000000-0fc51e8f6b123f0a5982Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0002-9100000000-762070874ad885772dc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-0002-9100000000-d705002b3a24c5b5ac0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-002b-9000000000-caf9814ab914b2093561Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-004j-9000000000-3b04f1a6a67ed239b001Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-004i-9000000000-388ef99a8af7f88e6447Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-004i-9000000000-bc85bd9d38f2c4bf3c58Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0006-0190000000-ba22a78fbbfc1a90ace3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0a4i-0900000000-b559d4679fc0eaa79be7Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0002-9530000000-8e5076b641ebc42fb2efSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-0fdk-9870000000-6332e12e884d56a6c22bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-6469000000-934f8ed1edcbd28bc667Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-7295000000-a5ca0806e65ba8c99e88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9700000000-02fcc2f4b95b801c5949Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-8509000000-2992f67772e061c3ffe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-9ac5383c77bff5f6cb96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9d902dae0eabfe2165daSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04551
HMDB IDHMDB0001058
FooDB IDFDB022397
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDFRUCTOSE-16-DIPHOSPHATE
METLIN ID147
PDB IDBFP
Wikipedia LinkFructose 1,6-bisphosphate
Chemspider ID9848
ChEBI ID28013
PubChem Compound ID10267
Kegg Compound IDC05378
YMDB IDNot Available
ECMDB IDECMDB20123
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.
2. Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
3. 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):20-9, table of contents.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.
10. 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.