NP-MRD: Showing NP-Card for 4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid (NP0304360)

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Record Information

Version

2.0

Created at

2022-09-10 19:23:52 UTC

Updated at

2022-09-10 19:23:52 UTC

NP-MRD ID

NP0304360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid

Description

Esterastin belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid is found in Streptomyces lavendulae. 4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid was first documented in 1988 (PMID: 2852066). Based on a literature review a small amount of articles have been published on Esterastin (PMID: 8598537) (PMID: 7844032) (PMID: 2742868) (PMID: 2706657).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221232D          

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M  END

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M  END


  Mrv1652309102221232D          

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    4.3789   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1890   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291   -1.2070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4590    0.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088    0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687    1.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8388    2.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 33 28  1  4  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC1C(CC(C\C=C\C\C=C\CCCCC)OC(=O)C(CC(O)=N)N=C(C)O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46N2O6/c1-4-6-8-10-11-12-13-14-15-17-22(35-28(34)24(20-26(29)32)30-21(3)31)19-25-23(27(33)36-25)18-16-9-7-5-2/h11-12,14-15,22-25H,4-10,13,16-20H2,1-3H3,(H2,29,32)(H,30,31)/b12-11+,15-14+

> <INCHI_KEY>
JKNGELGDDBUFHG-TVYVBBRWSA-N

> <FORMULA>
C28H46N2O6

> <MOLECULAR_WEIGHT>
506.684

> <EXACT_MASS>
506.335587209

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
58.22153661488634

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(4E,7E)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid

> <JCHEM_LOGP>
3.712328941590455

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.723633884320353

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.5459457387398388

> <JCHEM_PKA_STRONGEST_BASIC>
12.66199696832252

> <JCHEM_POLAR_SURFACE_AREA>
129.27

> <JCHEM_REFRACTIVITY>
152.31029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(4E,7E)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      13.215   5.023   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.702   4.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.694   5.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.182   5.605   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.174   6.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.662   6.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.158   5.023   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.645   4.732   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.141   3.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.629   2.986   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.125   1.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.133   0.366   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.629  -1.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.117  -1.380   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.253  -2.655   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.022  -1.792   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.534  -2.083   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.158  -0.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.449   0.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.905   1.500   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.196   3.012   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.651   3.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.942   5.028   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.397   5.533   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.645   0.657   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.653  -0.507   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.149  -1.962   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.166  -0.216   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.174  -1.380   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.686  -1.089   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      10.694  -2.253   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0      10.190   0.366   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       7.670   1.239   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       6.662   2.403   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.149   2.112   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.166   3.859   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆N₂O₆

Average Mass

506.6840 Da

Monoisotopic Mass

506.33559 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCCCC1C(CC(C\C=C\C\C=C\CCCCC)OC(=O)C(CC(O)=N)N=C(C)O)OC1=O

InChI Identifier

InChI=1S/C28H46N2O6/c1-4-6-8-10-11-12-13-14-15-17-22(35-28(34)24(20-26(29)32)30-21(3)31)19-25-23(27(33)36-25)18-16-9-7-5-2/h11-12,14-15,22-25H,4-10,13,16-20H2,1-3H3,(H2,29,32)(H,30,31)/b12-11+,15-14+

InChI Key

JKNGELGDDBUFHG-TVYVBBRWSA-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 lavendulae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Asparagine and derivatives

Alternative Parents

Substituents

Asparagine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid ester
Fatty acid ester
Fatty acyl
Fatty amide
Dicarboxylic acid or derivatives
Acetamide
Beta_propiolactone
Secondary carboxylic acid amide
Primary carboxylic acid amide
Oxetane
Lactone
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018189

Chemspider ID

11278335

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22256690

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Murakami S, Takahashi Y, Naganawa H, Takeuchi T, Aoyagi T: Belactins A and B, new serine carboxypeptidase inhibitors produced by Actinomycete. II. Physico-chemical properties, structure determinations and enzymatic inhibitory activities compared with other beta-lactone containing inhibitors. J Enzyme Inhib. 1995;9(4):277-84. doi: 10.3109/14756369509036556. [PubMed:8598537 ]
Yoshinari K, Aoki M, Ohtsuka T, Nakayama N, Itezono Y, Mutoh M, Watanabe J, Yokose K: Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation. J Antibiot (Tokyo). 1994 Dec;47(12):1376-84. doi: 10.7164/antibiotics.47.1376. [PubMed:7844032 ]
Morin RJ, Peng SK: Relative specificities of inhibition of acid cholesteryl ester hydrolase and neutral cholesteryl ester hydrolase in cultured rabbit aortic smooth muscle cells by esterastin and cholesteryl oleyl ether. Biochim Biophys Acta. 1989 Jul 17;1004(1):139-42. doi: 10.1016/0005-2760(89)90224-5. [PubMed:2742868 ]
Kanai M: Ultrastructural and biochemical studies of lipolysis by lipolysosomes in chick hepatocytes. Cell Tissue Res. 1989 Mar;255(3):559-65. doi: 10.1007/BF00218791. [PubMed:2706657 ]
Mineo C, Kanaseki T, Enomoto M, Ohkuma S, Takano T: Intracellular transport of cholesteryl esters from lysosomes to cytoplasm in macrophages. Cell Struct Funct. 1988 Oct;13(5):435-43. doi: 10.1247/csf.13.435. [PubMed:2852066 ]
LOTUS database [Link]

Showing NP-Card for 4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid (NP0304360)

MOL for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

3D MOL for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

3D SDF for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

3D-SDF for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

PDB for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

3D PDB for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

SMILES for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

INCHI for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

Structure for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)

3D Structure for NP0304360 (4-{[(4e,7e)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-oxobutanimidic acid)