NP-MRD: Showing NP-Card for acivicin (NP0241610)

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Record Information

Version

2.0

Created at

2022-09-07 01:44:21 UTC

Updated at

2022-09-07 01:44:21 UTC

NP-MRD ID

NP0241610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acivicin

Description

Acivicin, also known as antibiotic at 125 or AT-125, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. It is obtained as a fermentation product of Streptomyces sviceus bacteria. Acivicin is a very strong basic compound (based on its pKa). An L-alpha-amino acid that is L-alanine in which the methyl group is replaced by a (5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl group. acivicin is found in Streptomyces sviceus. acivicin was first documented in 1987 (PMID: 3112985). A glutamine analogue antimetabolite, it interferes with glutamate metabolism and several glutamate-dependent synthetic enzymes (PMID: 11478776) (PMID: 14586123) (PMID: 2383250) (PMID: 2894949).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4   11   12                                             
CONECT    3    1    6    8                                                  
CONECT    4    2    5    7   13                                             
CONECT    5    4    9   10                                                  
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    3   11                                                       
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    2    8                                                       
CONECT   12    2                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
(alpha-S,5S)-alpha-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid	ChEBI
(AlphaS,5S)-alpha-amino-3-chloro-2-isoxazoline-5-acetic acid	ChEBI
Acivicine	ChEBI
Acivicino	ChEBI
Acivicinum	ChEBI
Antibiotic at 125	ChEBI
AT 125	ChEBI
AT-125	ChEBI
NSC 163501	ChEBI
NSC-163501	ChEBI
U 42126	ChEBI
U-42,126	ChEBI
(a-S,5S)-a-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetate	Generator
(a-S,5S)-a-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid	Generator
(alpha-S,5S)-alpha-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetate	Generator
(Α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetate	Generator
(Α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid	Generator
(AlphaS,5S)-a-amino-3-chloro-2-isoxazoline-5-acetate	Generator
(AlphaS,5S)-a-amino-3-chloro-2-isoxazoline-5-acetic acid	Generator
(AlphaS,5S)-alpha-amino-3-chloro-2-isoxazoline-5-acetate	Generator
(AlphaS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetate	Generator
(AlphaS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetic acid	Generator
L-(AlphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid	MeSH
alpha-S,5S-alpha-amino-3-chloro-2-Isoxazoline-5-acetic acid	MeSH
alpha-amino-3-chloro-4,5-dihydro-5-Isoxazoleacetic acid	MeSH

Chemical Formula

C₅H₇ClN₂O₃

Average Mass

178.5740 Da

Monoisotopic Mass

178.01452 Da

IUPAC Name

(2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

Traditional Name

acivicin

CAS Registry Number

Not Available

SMILES

[H][C@@](N)(C(O)=O)[C@]1([H])CC(Cl)=NO1

InChI Identifier

InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1

InChI Key

QAWIHIJWNYOLBE-OKKQSCSOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sviceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Isoxazoline
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:74545 )
non-proteinogenic L-alpha-amino acid (CHEBI:74545 )
isoxazoles (CHEBI:74545 )

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	-2.6	ALOGPS
logP	-2.7	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.4	ChemAxon
pKa (Strongest Basic)	8.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.4 m³·mol⁻¹	ChemAxon
Polarizability	14.96 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1036

BiGG ID

Not Available

Wikipedia Link

Acivicin

METLIN ID

Not Available

PubChem Compound

294641

PDB ID

Not Available

ChEBI ID

74545

Good Scents ID

Not Available

References

General References

Aberkane H, Frank P, Galteau MM, Wellman M: Acivicin induces apoptosis independently of gamma-glutamyltranspeptidase activity. Biochem Biophys Res Commun. 2001 Aug 3;285(5):1162-7. doi: 10.1006/bbrc.2001.5297. [PubMed:11478776 ]
Miyake T, Sammoto H, Ono B: Acivicin induce filamentous growth of Saccharomyces cerevisiae. Biosci Biotechnol Biochem. 2003 Oct;67(10):2283-5. doi: 10.1271/bbb.67.2283. [PubMed:14586123 ]
Mukherjee T, Roy K, Bhaduri A: Acivicin: a highly active potential chemotherapeutic agent against visceral leishmaniasis. Biochem Biophys Res Commun. 1990 Jul 31;170(2):426-32. doi: 10.1016/0006-291x(90)92109-d. [PubMed:2383250 ]
McGovren JP, Williams MG, Stewart JC: Interspecies comparison of acivicin pharmacokinetics. Drug Metab Dispos. 1988 Jan-Feb;16(1):18-22. [PubMed:2894949 ]
Chance WT, Cao L, Nelson JL, Foley-Nelson T, Fischer JE: Acivicin reduces tumor growth during total parenteral nutrition (TPN). Surgery. 1987 Aug;102(2):386-94. [PubMed:3112985 ]
LOTUS database [Link]

Showing NP-Card for acivicin (NP0241610)

MOL for NP0241610 (acivicin)

3D MOL for NP0241610 (acivicin)

3D SDF for NP0241610 (acivicin)

3D-SDF for NP0241610 (acivicin)

PDB for NP0241610 (acivicin)

3D PDB for NP0241610 (acivicin)

SMILES for NP0241610 (acivicin)

INCHI for NP0241610 (acivicin)

Structure for NP0241610 (acivicin)

3D Structure for NP0241610 (acivicin)