Showing Compound Card for 6-Phosphogluconic acid (CDB004906)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:49:06 UTC
Updated at2020-11-18 16:38:58 UTC
CannabisDB IDCDB004906
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name6-Phosphogluconic acid
Description6-Phosphogluconic acid, also known as 6-phospho-D-gluconate or gluconate 6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. A gluconic acid phosphate having the phosphate group at the 6-position. 6-Phosphogluconic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans. Within humans, 6-phosphogluconic acid participates in a number of enzymatic reactions. In particular, 6-phosphogluconic acid can be biosynthesized from gluconolactone through its interaction with the enzyme 6-phosphogluconolactonase. In addition, 6-phosphogluconic acid can be converted into D-ribulose 5-phosphate through the action of the enzyme 6-phosphogluconate dehydrogenase, decarboxylating. In humans, 6-phosphogluconic acid is involved in the metabolic disorder called the glucose-6-phosphate dehydrogenase deficiency pathway. Outside of the human body, 6-Phosphogluconic acid has been detected, but not quantified in, several different foods, such as teffs, chinese chestnuts, cottonseeds, irish moss, and red beetroots. This could make 6-phosphogluconic acid a potential biomarker for the consumption of these foods. 6-Phosphogluconic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6-Phospho-D-gluconateChEBI
6-Phospho-D-gluconic acidGenerator
6-PhosphogluconateGenerator
6-O-Phosphono-D-gluconic acidHMDB
6-p-GluconateHMDB
D-Gluconic acid 6-(dihydrogen phosphate)HMDB
D-Gluconic acid 6-phosphateHMDB
Gluconic acid-6-phosphateHMDB
Gluconate 6-phosphateHMDB
Chemical FormulaC6H13O10P
Average Molecular Weight276.14
Monoisotopic Molecular Weight276.0246
IUPAC Name(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid
Traditional Name6-phosphogluconic acid
CAS Registry Number921-62-0
SMILES
O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1
InChI KeyBIRSGZKFKXLSJQ-SQOUGZDYSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Gluconic_acid
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Monoalkyl phosphate
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alkyl phosphate
  • Fatty acid
  • Alpha-hydroxy acid
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Hydroxy acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-3.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area184.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.14 m³·mol⁻¹ChemAxon
Polarizability21.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS6-Phosphogluconic acid, 5 TMS, GC-MS Spectrumsplash10-0uxu-0933000000-d0c837bb667abbae2ce0Spectrum
GC-MS6-Phosphogluconic acid, 7 TMS, GC-MS Spectrumsplash10-00ks-1978000000-c7702d284ad9f06bb5c0Spectrum
GC-MS6-Phosphogluconic acid, non-derivatized, GC-MS Spectrumsplash10-0uxu-0933000000-d0c837bb667abbae2ce0Spectrum
GC-MS6-Phosphogluconic acid, non-derivatized, GC-MS Spectrumsplash10-00ks-1978000000-c7702d284ad9f06bb5c0Spectrum
Predicted GC-MS6-Phosphogluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-9430000000-e4198ba354325082e116Spectrum
Predicted GC-MS6-Phosphogluconic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-7192047000-e8fa0bd25a22fa6fd28bSpectrum
Predicted GC-MS6-Phosphogluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Phosphogluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b622012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff412012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d2182012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d2182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f5322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e126032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-002b-9100000000-15a83e588180be4c06642021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3d9937a328c6aa73fe8a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004j-7190000000-26e8b7b5ea3ee85cbb612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-002b-9100000000-39b6ad01fb7aa0ecbb1a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-01ow-3390000000-1a67f265724b65046d122020-07-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
6-phosphogluconolactonasePGLS19p13.2O95336 details
6-phosphogluconate dehydrogenase, decarboxylatingPGD1p36.22P52209 details
Putative uncharacterized protein PGDPGD1p36.3-p36.13A9Z1X1 details
Probable gluconokinaseIDNK9q21.32Q5T6J7 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001316
DrugBank IDDB02076
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030611
KNApSAcK IDC00007481
Chemspider ID82615
KEGG Compound IDC00345
BioCyc IDCPD-2961
BiGG ID34686
Wikipedia Link6-Phosphogluconic_acid
METLIN ID367
PubChem Compound91493
PDB IDNot Available
ChEBI ID48928
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. 6-phosphogluconolactonase
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:
PGLS
Uniprot ID:
O95336
Molecular weight:
27546.495
Enzyme Details
2. 6-phosphogluconate dehydrogenase, decarboxylating
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:
PGD
Uniprot ID:
P52209
Molecular weight:
53139.56
Enzyme Details
3. Putative uncharacterized protein PGD
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
PGD
Uniprot ID:
A9Z1X1
Molecular weight:
32311.5
Enzyme Details
4. Probable gluconokinase
General function:
Involved in shikimate kinase activity
Specific function:
Not Available
Gene Name:
IDNK
Uniprot ID:
Q5T6J7
Molecular weight:
20577.63