NP-MRD: Showing NP-Card for Azaserine (NP0004747)

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Record Information

Version

1.0

Created at

2020-12-09 02:10:04 UTC

Updated at

2021-07-15 16:50:03 UTC

NP-MRD ID

NP0004747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azaserine

Provided By

NPAtlas

Description

Azaserine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Azaserine is found in Streptomyces sp. It was first documented in 1954 (PMID: 13132877). Based on a literature review a significant number of articles have been published on azaserine (PMID: 19136606) (PMID: 23101568) (PMID: 23301939) (PMID: 4951003).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 19 18  0  0  0  0            999 V2000
    4.0580    1.4156   -0.5444 N   0  5  0  0  0  2  0  0  0  0  0  0
    3.6257    0.2464   -0.4845 N   0  3  0  0  0  4  0  0  0  0  0  0
    3.1696   -0.9036   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.0924   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651   -1.8412   -1.0184 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0737   -0.4107    0.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2963   -0.4800    0.9772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1345   -0.0328   -0.2052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7750    1.3451   -0.4896 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5696   -0.0702    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1057   -1.1559    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3063    1.1114    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165   -1.7559   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5120    0.2628    1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6346   -1.4545    1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791   -0.7092   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    1.8369    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5040    1.7815   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9807    1.9067    0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  6  0  0  0
  9 17  1  0  0  0  0
  9 18  1  0  0  0  0
 12 19  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0004747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])OC(=O)C([H])=[N+]=[N-]

> <INCHI_IDENTIFIER>
InChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1

> <INCHI_KEY>
MZZGOOYMKKIOOX-VKHMYHEASA-N

> <FORMULA>
C5H7N3O4

> <MOLECULAR_WEIGHT>
173.1268

> <EXACT_MASS>
173.043655727

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.510513701392977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-{[2-(-lambda4,-lambda2-diazynylidene)acetyl]oxy}propanoic acid

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-4.60003307229755

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.993470892540156

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.554880503573027

> <JCHEM_PKA_STRONGEST_BASIC>
8.375878169132827

> <JCHEM_POLAR_SURFACE_AREA>
106.69000000000001

> <JCHEM_REFRACTIVITY>
34.748799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[2-(-lambda4,-lambda2-diazynylidene)acetyl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0       4.058   1.416  -0.544  0.00  0.00           N-1
HETATM    2  N   UNK     0       3.626   0.246  -0.485  0.00  0.00           N+1
HETATM    3  C   UNK     0       3.170  -0.904  -0.389  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.740  -1.092  -0.270  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.065  -1.841  -1.018  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.074  -0.411   0.726  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.296  -0.480   0.977  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.135  -0.033  -0.205  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.775   1.345  -0.490  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.570  -0.070   0.246  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.106  -1.156   0.548  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.306   1.111   0.326  0.00  0.00           O+0
HETATM   13  H   UNK     0       3.817  -1.756  -0.394  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.512   0.263   1.799  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.635  -1.454   1.371  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.979  -0.709  -1.051  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.751   1.837   0.446  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.504   1.782  -1.129  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.981   1.907   0.866  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   14   15                                             
CONECT    8    7    9   10   16                                             
CONECT    9    8   17   18                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   19                                                       
CONECT   13    3                                                            
CONECT   14    7                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Azaserina	ChEBI
Azaserinum	ChEBI
L-Azaserine	ChEBI
L-beta-(Diazoacetoxy)alanin	ChEBI
L-beta-(Diazoacetoxy)alanine	ChEBI
L-Serine diazoacetate	ChEBI
L-Serine diazoacetate ester	ChEBI
L-b-(Diazoacetoxy)alanin	Generator
L-Β-(diazoacetoxy)alanin	Generator
L-b-(Diazoacetoxy)alanine	Generator
L-Β-(diazoacetoxy)alanine	Generator
L-Serine diazoacetic acid	Generator
L-Serine diazoacetic acid ester	Generator
Azeserine	MeSH
O Diazoacetyl L serine	MeSH
O-Diazoacetyl-L-serine	MeSH

Chemical Formula

C₅H₇N₃O₄

Average Mass

173.1268 Da

Monoisotopic Mass

173.04366 Da

IUPAC Name

(2S)-2-amino-3-{[2-(-lambda4,-lambda2-diazynylidene)acetyl]oxy}propanoic acid

Traditional Name

(2S)-2-amino-3-{[2-(-lambda4,-lambda2-diazynylidene)acetyl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](COC(=O)C=[N+]=[N-])C(O)=O

InChI Identifier

InChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1

InChI Key

MZZGOOYMKKIOOX-VKHMYHEASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 sp.	NPAtlas	13132877

Chemical Taxonomy

Description

This compound 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
Alpha-diazo ester
Dicarboxylic acid or derivatives
Carboxylic acid ester
Amino acid
Diazo compound
Carboxylic acid
Hydrocarbon derivative
Organic zwitterion
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxide
Carbonyl group
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:74846 )
non-proteinogenic L-alpha-amino acid (CHEBI:74846 )
L-serine derivative (CHEBI:74846 )
diazo compound (CHEBI:74846 )

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	-4.6	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	1.55	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	34.75 m³·mol⁻¹	ChemAxon
Polarizability	14.51 Å³	ChemAxon
Number of Rings	0	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

NPAtlas ID

NPA003365

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16735688

KEGG Compound ID

C19194

BioCyc ID

L-AZASERINE

BiGG ID

Not Available

Wikipedia Link

Azaserine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

74846

Good Scents ID

Not Available

References

General References

BARTZ QR, ELDER CC, FROHARDT RP, FUSARI SA, HASKELL TH, JOHANNESSEN DW, RYDER A: Isolation and characterization of azaserine. Nature. 1954 Jan 9;173(4393):72-3. doi: 10.1038/173072b0. [PubMed:13132877 ]
Rajapakse AG, Ming XF, Carvas JM, Yang Z: The hexosamine biosynthesis inhibitor azaserine prevents endothelial inflammation and dysfunction under hyperglycemic condition through antioxidant effects. Am J Physiol Heart Circ Physiol. 2009 Mar;296(3):H815-22. doi: 10.1152/ajpheart.00756.2008. Epub 2009 Jan 9. [PubMed:19136606 ]
Yener Y, Kalipci E, Oztas H, Aydin AD, Yildiz H: Possible neoplastic effects of acrylamide on rat exocrine pancreas. Biotech Histochem. 2013 Jan;88(1):47-53. doi: 10.3109/10520295.2012.733028. Epub 2012 Oct 29. [PubMed:23101568 ]
Vibjerg Jensen R, Johnsen J, Buus Kristiansen S, Zachara NE, Botker HE: Ischemic preconditioning increases myocardial O-GlcNAc glycosylation. Scand Cardiovasc J. 2013 Jun;47(3):168-74. doi: 10.3109/14017431.2012.756984. Epub 2013 Jan 10. [PubMed:23301939 ]
Protivinsky R: Azaserine. Antibiot Chemother (1971). 1971;17:95-100. doi: 10.1159/000392366. [PubMed:4951003 ]

Showing NP-Card for Azaserine (NP0004747)

MOL for NP0004747 (Azaserine)

3D MOL for NP0004747 (Azaserine)

3D SDF for NP0004747 (Azaserine)

3D-SDF for NP0004747 (Azaserine)

PDB for NP0004747 (Azaserine)

3D PDB for NP0004747 (Azaserine)

SMILES for NP0004747 (Azaserine)

INCHI for NP0004747 (Azaserine)

Structure for NP0004747 (Azaserine)

3D Structure for NP0004747 (Azaserine)