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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:10 UTC

Update Date

2023-02-21 17:19:20 UTC

HMDB ID

HMDB0029874

Secondary Accession Numbers

HMDB29874

Metabolite Identification

Common Name

Squamolone

Description

Squamolone belongs to the class of organic compounds known as pyrrolidinecarboxamides. These are pyrrolidines in which the pyrrolidine rings is substituted at one or more positions by a carboxamide group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Based on a literature review very few articles have been published on Squamolone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Carbamoyl-2-pyrrolidone	HMDB
2-oxo-1-Pyrrolidinecarboxamide, 9ci	HMDB
2-Oxopyrrolidine-1-carboximidate	HMDB

Chemical Formula

C₅H₈N₂O₂

Average Molecular Weight

128.1292

Monoisotopic Molecular Weight

128.05857751

IUPAC Name

2-oxopyrrolidine-1-carboxamide

Traditional Name

2-oxopyrrolidine-1-carboxamide

CAS Registry Number

40451-67-0

SMILES

NC(=O)N1CCCC1=O

InChI Identifier

InChI=1S/C5H8N2O2/c6-5(9)7-3-1-2-4(7)8/h1-3H2,(H2,6,9)

InChI Key

XYVMBSCIEDOIJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidinecarboxamides. These are pyrrolidines in which the pyrrolidine rings is substituted at one or more positions by a carboxamide group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidine carboxylic acids and derivatives

Direct Parent

Pyrrolidinecarboxamides

Alternative Parents

Substituents

Pyrrolidine-1-carboxamide
N-acyl urea
Ureide
Pyrrolidone
2-pyrrolidone
Dicarboximide
Urea
Carbonic acid derivative
Lactam
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029874)
Cytoplasm (HMDB: HMDB0029874)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029874)

Source

Endogenous

Endogenous (HMDB: HMDB0029874)

Plant

Plant (HMDB: HMDB0029874)

Exogenous

Food

Food (HMDB: HMDB0029874)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	148 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10370 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	504 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.92	ChemAxon
logS	0.59	ALOGPS
pKa (Strongest Acidic)	15.27	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.4 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.5 m³·mol⁻¹	ChemAxon
Polarizability	12.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.851	31661259
DarkChem	[M-H]-	119.978	31661259
DeepCCS	[M+H]+	126.969	30932474
DeepCCS	[M-H]-	124.122	30932474
DeepCCS	[M-2H]-	160.666	30932474
DeepCCS	[M+Na]+	135.612	30932474
AllCCS	[M+H]+	127.3	32859911
AllCCS	[M+H-H2O]+	122.7	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.9	32859911
AllCCS	[M-H]-	122.3	32859911
AllCCS	[M+Na-2H]-	124.5	32859911
AllCCS	[M+HCOO]-	126.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Squamolone	NC(=O)N1CCCC1=O	2056.0	Standard polar	33892256
Squamolone	NC(=O)N1CCCC1=O	1410.0	Standard non polar	33892256
Squamolone	NC(=O)N1CCCC1=O	1403.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Squamolone,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1CCCC1=O	1537.2	Semi standard non polar	33892256
Squamolone,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1CCCC1=O	1474.0	Standard non polar	33892256
Squamolone,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1CCCC1=O)[Si](C)(C)C	1621.0	Semi standard non polar	33892256
Squamolone,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1CCCC1=O)[Si](C)(C)C	1617.5	Standard non polar	33892256
Squamolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1CCCC1=O	1776.2	Semi standard non polar	33892256
Squamolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1CCCC1=O	1715.0	Standard non polar	33892256
Squamolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1CCCC1=O)[Si](C)(C)C(C)(C)C	2017.3	Semi standard non polar	33892256
Squamolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1CCCC1=O)[Si](C)(C)C(C)(C)C	2069.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Squamolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-5ec6c50b596e385ce14b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Squamolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Squamolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 10V, Positive-QTOF	splash10-004i-1900000000-aac63fa09160573937bf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 20V, Positive-QTOF	splash10-000i-9400000000-4f8020e2d61f7464ed6c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 40V, Positive-QTOF	splash10-0006-9100000000-7d186356d6d9c3863300	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 10V, Negative-QTOF	splash10-0006-9100000000-3bda9d29292d89e66070	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 20V, Negative-QTOF	splash10-001i-9100000000-3de90964182b54553ec7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 40V, Negative-QTOF	splash10-0006-9000000000-a1550c82199e17ddaf3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 10V, Negative-QTOF	splash10-001i-9000000000-b45947920e826ae785ea	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 20V, Negative-QTOF	splash10-0159-9000000000-747bb57836c2a44b9700	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 10V, Positive-QTOF	splash10-000i-9400000000-801640e961b253f13a63	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 20V, Positive-QTOF	splash10-01q0-9400000000-419eb69e82f871462038	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamolone 40V, Positive-QTOF	splash10-0006-9000000000-b82cee6ed6632befa24d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB001103

KNApSAcK ID

C00046415

Chemspider ID

289577

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

326996

PDB ID

Not Available

ChEBI ID

565546

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1811911

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Squamolone (HMDB0029874)

MOL for HMDB0029874 (Squamolone)

3D MOL for HMDB0029874 (Squamolone)

3D SDF for HMDB0029874 (Squamolone)

3D-SDF for HMDB0029874 (Squamolone)

PDB for HMDB0029874 (Squamolone)

3D PDB for HMDB0029874 (Squamolone)

SMILES for HMDB0029874 (Squamolone)

INCHI for HMDB0029874 (Squamolone)

Structure for HMDB0029874 (Squamolone)

3D Structure for HMDB0029874 (Squamolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra