Milk Composition Database: Showing metabocard for Cycloserine (BMDB0062042)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-06-25 21:46:12 UTC

Update Date

2020-04-22 15:51:12 UTC

MCDB ID

BMDB0062042

Secondary Accession Numbers

BMDB62042

Metabolite Identification

Common Name

Cycloserine

Description

Cycloserine, also known as alpha-cycloserine or seromycin, belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms. Thus, cycloserine is considered to be a non-ribosomal peptide/polyketide hybrid lipid molecule. Cycloserine is a drug which is used in combination with up to 5 other drugs as a treatment for mycobacterium avium complex (mac) and is also used to treat tuberculosis (tb). Cycloserine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-4-Amino-3-isoxazolidinone	ChEBI
(+)-Cycloserine	ChEBI
(R)-4-AMINO-isoxazolidin-3-one	ChEBI
alpha-Cycloserine	ChEBI
Cicloserina	ChEBI
Cyclo-D-serine	ChEBI
Cycloserinum	ChEBI
D-(+)-Cycloserine	ChEBI
D-4-Amino-3-isoxazolidinone	ChEBI
D-4-Amino-3-isoxazolidone	ChEBI
DCS	ChEBI
Orientomycin	ChEBI
PA 94	ChEBI
PA-94	ChEBI
Ro-1-9213	ChEBI
Seromycin	ChEBI
D-Cycloserine	Kegg
ABBR DCS	Kegg
a-Cycloserine	Generator
Α-cycloserine	Generator
D-CS	HMDB
D-Cycloserine synth. BP 88	HMDB
D-Cycloserine, synthetic	HMDB
D-Oxamicina	HMDB
D-Oxamycin	HMDB
DL-Cycloserine	HMDB
L-Cycloserine	HMDB
R-4-Amino-3-isoxazolidinone	HMDB

Chemical Formula

C₃H₆N₂O₂

Average Molecular Weight

102.0919

Monoisotopic Molecular Weight

102.042927446

IUPAC Name

(4R)-4-amino-1,2-oxazolidin-3-one

Traditional Name

cycloserine

CAS Registry Number

68-41-7

SMILES

[H][C@@]1(N)CON=C1O

InChI Identifier

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

InChI Key

DYDCUQKUCUHJBH-UWTATZPHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Isoxazolines

Direct Parent

Isoxazolines

Alternative Parents

Substituents

Isoxazoline
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organooxygen heterocyclic antibiotic (CHEBI:40009 )
organonitrogen heterocyclic antibiotic (CHEBI:40009 )
4-amino-1,2-oxazolidin-3-one (CHEBI:40009 )
Non-ribosomal peptide/polyketide hybrids (C08057 )
Non-ribosomal peptide/polyketide hybrids (LMPK14000007 )

Physical Properties

State

Not Available

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	-1.3	ALOGPS
logP	-2.4	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.35 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.85 m³·mol⁻¹	ChemAxon
Polarizability	8.87 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
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0uy0-5900000000-06bce0b228f324fe49b4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0uy0-5900000000-06bce0b228f324fe49b4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0e7a5a8b0f7ce48e4509	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-4900000000-f1c1692f9e6318f52377	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9300000000-45585d9e68724372ca94	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-9000000000-bac95a810bc34e20e690	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-5babaf58090cc358ab6e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-9300000000-0ff851b2ef4ce71985ff	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9000000000-8a39f19e4a34080991d1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-9800000000-28ac2fbbebd31cc6100b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-739f88bc4c62ad6e99a6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-940c87bcfe09a2af1fc9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w2c-9400000000-13b86532b272b0b5785d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a3d694a542f40615fe9e	2021-09-23	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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
1D NMR	¹³C 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: 25599412	details
Detected but not Quantified	Not Applicable		PMID: 23438684	details

External Links

HMDB ID

HMDB0014405

DrugBank ID

DB00260

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB098104

KNApSAcK ID

Not Available

Chemspider ID

5998

KEGG Compound ID

C08057

BioCyc ID

CPD-2482

BiGG ID

Not Available

Wikipedia Link

Cycloserine

METLIN ID

Not Available

PubChem Compound

6234

PDB ID

4AX

ChEBI ID

40009

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]

Showing metabocard for Cycloserine (BMDB0062042)

Structure for BMDB0062042 (Cycloserine)