Milk Composition Database: Showing metabocard for Homocysteine thiolactone (BMDB0002287)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:53:39 UTC

Update Date

2020-04-22 15:10:31 UTC

MCDB ID

BMDB0002287

Secondary Accession Numbers

BMDB02287

Metabolite Identification

Common Name

Homocysteine thiolactone

Description

Homocysteine thiolactone, also known as ( -)-3-amino-2-thiolanon, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Homocysteine thiolactone is possibly soluble (in water) and a very strong basic compound (based on its pKa).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
( -)-3-amino-2-Thiolanon	HMDB
( -)-3-aminotetrahydro-2-Thiophenon	HMDB
(+-)-3-aminodihydro-2(3H)-Thiophenone	HMDB
3-aminodihydro-2(3H)-Thiophenone	HMDB
DL-3-aminotetrahydro-2-Thiophenone	HMDB
DL-Homocysteine thiolactone	HMDB
L-Homocysteine thiolactone	HMDB

Chemical Formula

C₄H₇NOS

Average Molecular Weight

117.169

Monoisotopic Molecular Weight

117.024834541

IUPAC Name

3-aminothiolan-2-one

Traditional Name

DL-homocysteine thiolactone

CAS Registry Number

3622-59-1

SMILES

NC1CCSC1=O

InChI Identifier

InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2

InChI Key

KIWQWJKWBHZMDT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Thiolane
Carbothioic s-lactone
Thiocarboxylic acid ester
Thiolactone
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.51	ALOGPS
logP	-0.25	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	29.76 m³·mol⁻¹	ChemAxon
Polarizability	11.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-9000000000-7b8e6410972444b84efc	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-8f683c9002bf43fef10d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0076-9000000000-e26ebbd2d16a1aed5801	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-649e7b0f78d61a745b45	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-806166a012352ec0be63	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aba-9000000000-a8839b6dcc9998e5eadc	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0080-9000000000-97c8bd4bc30856bdda2e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-a86fe79188b92a0f513e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-9100000000-bed3e8f03e106eedf1a8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-cfcd40acf2ab07b3f5f3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-6900000000-587ed663ed27e0d79f57	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9600000000-974a58cb3346970c79ff	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052o-9000000000-4073e682ce58bd088e4e	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 26686724	details

External Links

HMDB ID

HMDB0002287

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022949

KNApSAcK ID

Not Available

Chemspider ID

96881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6594

PubChem Compound

107712

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Takehara, Jun; Ichikawa, Shuji; Iwane, Hiroshi. Preparation of DL-homocysteine thiolactone inorganic acid salts. Jpn. Kokai Tokkyo Koho (1998), 4 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Showing metabocard for Homocysteine thiolactone (BMDB0002287)

Structure for BMDB0002287 (Homocysteine thiolactone)