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Showing Compound Fenugreekine (FDB019002)

Record Information
Version1.0
Creation date2010-04-08 22:14:04 UTC
Update date2019-11-26 03:16:59 UTC
Primary IDFDB019002
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFenugreekine
DescriptionFenugreekine, also known as PAD, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Fenugreekine is a strong basic compound (based on its pKa). Fenugreekine is found, on average, in the highest concentration within fenugreeks. Fenugreekine has also been detected, but not quantified in, herbs and spices. This could make fenugreekine a potential biomarker for the consumption of these foods.
CAS Number55069-02-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
PADHMDB
6-[(2S,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]pyridine-2-carboximidateHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.15 g/LALOGPS
logP-1.6ALOGPS
logP-6.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area327.27 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity140.48 m³·mol⁻¹ChemAxon
Polarizability57.65 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H27N7O14P2
IUPAC name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5S)-5-(6-carbamoylpyridin-2-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
InChI IdentifierInChI=1S/C21H27N7O14P2/c22-18-12-20(25-6-24-18)28(7-26-12)21-16(32)14(30)11(41-21)5-39-44(36,37)42-43(34,35)38-4-10-13(29)15(31)17(40-10)8-2-1-3-9(27-8)19(23)33/h1-3,6-7,10-11,13-17,21,29-32H,4-5H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,17+,21-/m1/s1
InChI KeyLFERELMXERXKKQ-KMXXXSRASA-N
Isomeric SMILESNC(=O)C1=NC(=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
Average Molecular Weight663.4251
Monoisotopic Molecular Weight663.109121631
Classification
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Pyridine carboxylic acid or derivatives
  • Imidazopyrimidine
  • 2-heteroaryl carboxamide
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Pyridine
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Amino acid or derivatives
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointMp 202-208°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +43 (c, 0.528 in AcOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01td-0401903000-41180d860659695687a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931104000-f91bb8253f044d903a06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-e7559e90e95d5c52ec01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-85d10e6b53f747547df2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-0900308000-93951bb77cb4b40784b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1901100000-a46aae5f2908b6028aceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-5a276c37bb06448067b0JSpectraViewer
ChemSpider ID392166
ChEMBL IDCHEMBL1235132
KEGG Compound IDNot Available
Pubchem Compound ID444170
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39421
CRC / DFC (Dictionary of Food Compounds) IDLNP01-Z:LNP01-Z
EAFUS IDNot Available
Dr. Duke IDFENUGREEKINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPAD
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti hypotensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti vaccinia22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypotensiveDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
viristatDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).