Showing Compound Pyrrole (FDB014718)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:26 UTC

Update date

2019-11-26 03:10:39 UTC

Primary ID

FDB014718

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pyrrole

Description

Flavouring ingredient Pyrrole has very low basicity compared to conventional amines and some other aromatic compounds like pyridine. This decreased basicity is attributed to the delocalization of the lone pair of electrons of the nitrogen atom in the aromatic ring. Pyrrole is a very weak base with a pKaH of about ?4. Protonation results in loss of aromaticity, and is, therefore, unfavorable.; Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. Substituted derivatives are also called pyrroles. For example, C4H4NCH3 is N-methylpyrrole. Porphobilinogen is a trisubstituted pyrrole, which is the biosynthetic precursor to many natural products.; The starting materials in the Piloty-Robinson pyrrole synthesis are 2 equivalents of an aldehyde and hydrazine. The product is a pyrrole with specific substituents in the 3 and 4 positions. The aldehyde reacts with the diamine to an intermediate di-imine (R?C=N?N=C?R), which, with added hydrochloric acid, gives ring-closure and loss of ammonia to the pyrrole. Pyrrole is found in tamarind and corn.

CAS Number

109-97-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 10 of 18 entries

Predicted Properties

Property	Value	Source
Water Solubility	445 g/L	ALOGPS
logP	0.76	ALOGPS
logP	1.05	ChemAxon
logS	0.82	ALOGPS
pKa (Strongest Acidic)	18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.82 m³·mol⁻¹	ChemAxon
Polarizability	7.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H5N

IUPAC name

1H-pyrrole

InChI Identifier

InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H

InChI Key

KAESVJOAVNADME-UHFFFAOYSA-N

Isomeric SMILES

N1C=CC=C1

Average Molecular Weight

67.0892

Monoisotopic Molecular Weight

67.042199165

Classification

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrole (CHEBI:19203 )
a pyrrole (CPD-13300 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Anti-inflammatory

Antineoplastic agent:

Antitumor

Household products:

Antimicrobial agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp761 130-131°	DFC
Charge	Not Available
Density	d204 0.97	DFC
Experimental logP	0.75	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Experimental Water Solubility	45 mg/mL at 25 oC	RIDDICK,JA et al. (1986)
Isoelectric point	Not Available
Mass Composition	C 71.61%; H 7.51%; N 20.88%	DFC
Melting Point	Mp -24°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00ko-9000000000-8908fc8793c6501dc2d0	2015-03-01	View Spectrum
Predicted GC-MS	Pyrrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-9000000000-f644c5fdd4d5f9db3117	Spectrum
Predicted GC-MS	Pyrrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-510c084e3c928fa514ae	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-150b960a1186c02653f7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-3bea04ffb045db51356d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9000000000-bb04398351cbc20c433b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-9b747cfdf2fe46d188ee	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-ac61df56d353d5acb48b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-8777c03f1c46a5fcce9d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-3f070060c5785123e18c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-3f070060c5785123e18c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02tc-9000000000-43982034e7a3a595201a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-e0673bc7e6a6226fb72e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-a3a7192ca6658a081b5b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-9000000000-972ac9fb6e8cbc34f0d3	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

19203

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35924

CRC / DFC (Dictionary of Food Compounds) ID

JVF90-J:JVF90-J

EAFUS ID

3266

Dr. Duke ID

PYRROLE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1009261

SuperScent ID

Not Available

Wikipedia ID

Pyrrole

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
ethereal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.