ChemFOnt: Showing chemical card for Epiprogoitrin (CFc000336361)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:29:27 UTC

Chemfont ID

CFc000336361

Molecule Identification

Common Name

Epiprogoitrin

Definition

Progoitrin, also known as 2(R)-2-hydroxy-3-butenyl glucosinolate or glucorapiferin, is a member of the class of compounds known as alkylglucosinolates. Alkylglucosinolates are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Progoitrin is soluble (in water) and an extremely strong acidic compound (based on its pKa). Progoitrin is a bitter tasting compound and can be found in a number of food items such as white cabbage, common cabbage, cabbage, and garden cress, which makes progoitrin a potential biomarker for the consumption of these food products. Progoitrin is a biochemical from the glucosinolate family that is found in some food, which is inactive but after ingestion is converted to goitrin. Goitrin decrease the thyroid hormone production .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Thio-b-D-glucopyranose 1-[3-hydroxy-N-(sulfooxy)-4-pentenimidate], 9ci	HMDB
2(R)-2-Hydroxy-3-butenyl glucosinolate	HMDB
2-Hydroxy-3-butenyl glucosinolate	HMDB
Glucorapiferin	HMDB
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonate	HMDB
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pent-4-en-1-ylidene)amino]oxy}sulphonate	HMDB
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pent-4-en-1-ylidene)amino]oxy}sulphonic acid	HMDB
Epi-progoitrin	HMDB
Epiprogoitrin	HMDB
Progoitrin, (S)-isomer	HMDB
Progoitrin, monopotassium salt	HMDB
Progoitrin	MeSH

Chemical Formula

C₁₁H₁₉NO₁₀S₂

Average Molecular Weight

389.399

Monoisotopic Molecular Weight

389.045037213

IUPAC Name

{[(E)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxysulfonic acid

CAS Registry Number

19237-18-4

SMILES

OCC1OC(S\C(CC(O)C=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C11H19NO10S2/c1-2-5(14)3-7(12-22-24(18,19)20)23-11-10(17)9(16)8(15)6(4-13)21-11/h2,5-6,8-11,13-17H,1,3-4H2,(H,18,19,20)/b12-7+

InChI Key

MYHSVHWQEVDFQT-KPKJPENVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0034071)

Food

Vegetable

Cabbage

Chinese cabbage (FooDB: FOOD00035)
Cauliflower (FooDB: FOOD00031)

Leaf vegetable

Garden cress (FooDB: FOOD00099)

Herb and spice

Spice

White mustard (FooDB: FOOD00413)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	28.8 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.34 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	80.66 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon