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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 21:36:52 UTC

Update Date

2021-09-23 21:36:55 UTC

HMDB ID

HMDB0302902

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hygrine

Description

Hygrine, also known as (+)-hygrine or (+)-N-methyl-2-acetonylpyrrolidine, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Hygrine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Hygrine can be found in pomegranate, which makes hygrine a potential biomarker for the consumption of this food product. Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves (0.2%). It was first isolated by Carl Liebermann in 1889 (along with a related compound cuscohygrine) as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Hygrine	ChEBI
(+)-N-Methyl-2-acetonylpyrrolidine	ChEBI
(R)-(+)-Hygrine	ChEBI
(R)-1-(1-Methyl-2-pyrrolidinyl)-2-propanone	ChEBI
(R)-Hygrine	ChEBI
1-[(2R)-1-Methylpyrrolidin-2-yl]acetone	ChEBI
Hygrine, 2-(14)C-labeled, (+-)-isomer	MeSH
1-[(2R)-1-Methyl-2-pyrrolidinyl]-2-propanone	PhytoBank
D-(+)-Hygrine	PhytoBank

Chemical Formula

C₈H₁₅NO

Average Molecular Weight

141.2108

Monoisotopic Molecular Weight

141.115364107

IUPAC Name

1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-one

Traditional Name

(+)-hygrine

CAS Registry Number

Not Available

SMILES

CN1CCC[C@@H]1CC(C)=O

InChI Identifier

InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1

InChI Key

ADKXZIOQKHHDNQ-MRVPVSSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Beta-aminoketone
N-alkylpyrrolidine
Pyrrolidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidine alkaloid (CHEBI:46750 )
1-(1-methylpyrrolidin-2-yl)acetone (CHEBI:46750 )
Pyrrolidine alkaloids (C06179 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302902)

Food

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	0.7	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	18.54	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.53 m³·mol⁻¹	ChemAxon
Polarizability	16.35 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	130.474	32859911
AllCCS	[M+H-H2O]+	125.939	32859911
AllCCS	[M+Na]+	135.925	32859911
AllCCS	[M+NH4]+	134.705	32859911
AllCCS	[M-H]-	133.494	32859911
AllCCS	[M+Na-2H]-	135.367	32859911
AllCCS	[M+HCOO]-	137.488	32859911
DeepCCS	[M+H]+	132.153	30932474
DeepCCS	[M-H]-	129.908	30932474
DeepCCS	[M-2H]-	166.046	30932474
DeepCCS	[M+Na]+	140.915	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hygrine,1TMS,isomer #1	CC(=C[C@H]1CCCN1C)O[Si](C)(C)C	1299.2	Semi standard non polar	33892256
Hygrine,1TMS,isomer #1	CC(=C[C@H]1CCCN1C)O[Si](C)(C)C	1248.8	Standard non polar	33892256
Hygrine,1TMS,isomer #1	CC(=C[C@H]1CCCN1C)O[Si](C)(C)C	1527.4	Standard polar	33892256
Hygrine,1TMS,isomer #2	C=C(C[C@H]1CCCN1C)O[Si](C)(C)C	1255.8	Semi standard non polar	33892256
Hygrine,1TMS,isomer #2	C=C(C[C@H]1CCCN1C)O[Si](C)(C)C	1287.3	Standard non polar	33892256
Hygrine,1TMS,isomer #2	C=C(C[C@H]1CCCN1C)O[Si](C)(C)C	1602.6	Standard polar	33892256
Hygrine,1TBDMS,isomer #1	CC(=C[C@H]1CCCN1C)O[Si](C)(C)C(C)(C)C	1517.0	Semi standard non polar	33892256
Hygrine,1TBDMS,isomer #1	CC(=C[C@H]1CCCN1C)O[Si](C)(C)C(C)(C)C	1414.0	Standard non polar	33892256
Hygrine,1TBDMS,isomer #1	CC(=C[C@H]1CCCN1C)O[Si](C)(C)C(C)(C)C	1705.8	Standard polar	33892256
Hygrine,1TBDMS,isomer #2	C=C(C[C@H]1CCCN1C)O[Si](C)(C)C(C)(C)C	1495.6	Semi standard non polar	33892256
Hygrine,1TBDMS,isomer #2	C=C(C[C@H]1CCCN1C)O[Si](C)(C)C(C)(C)C	1457.2	Standard non polar	33892256
Hygrine,1TBDMS,isomer #2	C=C(C[C@H]1CCCN1C)O[Si](C)(C)C(C)(C)C	1767.2	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 10V, Positive-QTOF	splash10-006x-0900000000-d869c1a4797976695581	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 20V, Positive-QTOF	splash10-0089-9700000000-10a0f5f6ec12b82bbc5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 40V, Positive-QTOF	splash10-0a4l-9000000000-11af857a1c0e2b5d6a31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 10V, Negative-QTOF	splash10-0006-0900000000-ef10ea96abb9f75c99d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 20V, Negative-QTOF	splash10-0006-4900000000-18db06f2c75c67b5525b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 40V, Negative-QTOF	splash10-0006-9200000000-f64616ba0c2529a37c01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 10V, Positive-QTOF	splash10-001m-9700000000-a3c1279a33df8d5e2cf6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 20V, Positive-QTOF	splash10-00dm-9600000000-96c2c9e3b3d5116e4e3f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 40V, Positive-QTOF	splash10-000x-9000000000-0e31ffa5e8b035e86505	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 10V, Negative-QTOF	splash10-0a4i-9200000000-ca70525d71e29bac3b62	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 20V, Negative-QTOF	splash10-052f-9300000000-f1a5136f1fa6b0a91257	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hygrine 40V, Negative-QTOF	splash10-0a4l-9000000000-a9f3c2e655c95c67e4ab	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

hygrine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

46750

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Hygrine (HMDB0302902)

MOL for HMDB0302902 (Hygrine)

3D MOL for HMDB0302902 (Hygrine)

3D SDF for HMDB0302902 (Hygrine)

3D-SDF for HMDB0302902 (Hygrine)

PDB for HMDB0302902 (Hygrine)

3D PDB for HMDB0302902 (Hygrine)

SMILES for HMDB0302902 (Hygrine)

INCHI for HMDB0302902 (Hygrine)

Structure for HMDB0302902 (Hygrine)

3D Structure for HMDB0302902 (Hygrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra