Showing Compound Fenugreekine (FDB019002)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:04 UTC

Update date

2019-11-26 03:16:59 UTC

Primary ID

FDB019002

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Fenugreekine

Description

Fenugreekine 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 found, on average, in the highest concentration within fenugreeks (Trigonella foenum-graecum). 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. Based on a literature review very few articles have been published on Fenugreekine.

CAS Number

55069-02-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
PAD	HMDB
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-carboximidate	Generator, HMDB

Predicted Properties

Property	Value	Source
Water Solubility	3.15 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-6.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	327.27 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	140.48 m³·mol⁻¹	ChemAxon
Polarizability	57.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C21H27N7O14P2

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 Identifier

InChI=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 Key

LFERELMXERXKKQ-KMXXXSRASA-N

Isomeric SMILES

NC(=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 Weight

663.4251

Monoisotopic Molecular Weight

663.109121631

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Mp 202-208°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D +43 (c, 0.528 in AcOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Fenugreekine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01td-0401903000-41180d860659695687a6	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenugreekine, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0931104000-f91bb8253f044d903a06	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-e7559e90e95d5c52ec01	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-85d10e6b53f747547df2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-0900308000-93951bb77cb4b40784b3	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1901100000-a46aae5f2908b6028ace	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-3900000000-5a276c37bb06448067b0	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0110009000-3d572f003c6a3ae3fec2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0962017000-c89702406c5f20a4523a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0911000000-c46a89e8dcdffce052a4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000009000-322bd51654ca9a3687fe	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0h0u-8201009000-318546366f608d3b3788	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-6918504000-5731f91a27a122282829	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

392166

ChEMBL ID

CHEMBL1235132

KEGG Compound ID

Not Available

Pubchem Compound ID

444170

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB39421

CRC / DFC (Dictionary of Food Compounds) ID

LNP01-Z:LNP01-Z

EAFUS ID

Not Available

Dr. Duke ID

FENUGREEKINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

PAD

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-hypotensive	52217	An agent that increases blood pressure, counteracting hypotension. Its biological role is to stimulate the cardiovascular system, and its therapeutic applications include treating shock, orthostatic hypotension, and severe hypotension. Key medical uses include emergency medicine and critical care.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-vaccinia	22587	An antibody that neutralizes the vaccinia virus, used to treat complications from smallpox vaccination, such as eczema vaccinatum and progressive vaccinia, by reducing viral replication and promoting healing.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Cardiotonic	38070	An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Hypoglycemic	35526	An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Viristat		An antiviral agent that inhibits the formation of virus particles, playing a role in preventing viral replication. Its therapeutic applications include treating viral infections, with key medical uses in managing diseases caused by viral pathogens.	DUKE