Record Information
Version1.0
Creation date2015-05-07 18:46:59 UTC
Update date2020-09-17 15:40:21 UTC
Primary IDFDB030188
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,3-bisphospho-D-glycerate
DescriptionGlyceric acid 1,3-biphosphate, also known as 1,3-bisphospho-D-glycerate or 3-phospho-D-glyceroyl phosphate, belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. The (R)-enantiomer of 3-phosphoglyceroyl dihydrogen phosphate. Glyceric acid 1,3-biphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceric acid 1,3-biphosphate exists in all living species, ranging from bacteria to humans. Within humans, glyceric acid 1,3-biphosphate participates in a number of enzymatic reactions. In particular, glyceric acid 1,3-biphosphate can be biosynthesized from D-glyceraldehyde 3-phosphate; which is catalyzed by the enzyme glyceraldehyde-3-phosphate dehydrogenase. In addition, glyceric acid 1,3-biphosphate can be biosynthesized from 3-phosphoglyceric acid through the action of the enzyme pantothenate kinase 1. In humans, glyceric acid 1,3-biphosphate is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Outside of the human body, Glyceric acid 1,3-biphosphate has been detected, but not quantified in, several different foods, such as cherry tomato, jostaberries, canada blueberries, lovages, and mamey sapotes. This could make glyceric acid 1,3-biphosphate a potential biomarker for the consumption of these foods.
CAS Number38168-82-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility9.64 g/LALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H8O10P2
IUPAC name{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1
InChI KeyLJQLQCAXBUHEAZ-UWTATZPHSA-N
Isomeric SMILESO[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
Classification
Description Belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Glyceric_acid
  • Monoalkyl phosphate
  • Monosaccharide
  • Alkyl phosphate
  • Carboxylic acid salt
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,3-bisphospho-D-glycerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9500000000-cb3071f9249ee92b7d2cSpectrum
Predicted GC-MS1,3-bisphospho-D-glycerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1950000000-2cde7b5739871a8825422015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3910000000-72f2c46eab20369380562015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9500000000-c835034f0ac11618922d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-6190000000-6f4870543fc6131d14a72015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d9d9c6d217a255d791fd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1fef400a1ea8ca54c8022015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0090000000-def40aa9bb3094302ce82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-9040000000-374a9ff8c866f10f2f3c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4bf2b9a14f4e1c8fc62a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1390000000-8fe62bbfc56bf59f28a62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9410000000-e17767e21640a6f815322021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-c41dab2684b9d54afd312021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference