NP-MRD: Showing NP-Card for 5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid (NP0197586)

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Record Information

Version

2.0

Created at

2022-09-04 15:52:25 UTC

Updated at

2022-09-04 15:52:25 UTC

NP-MRD ID

NP0197586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid

Description

5-(Acetyloxy)-N-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. 5-(Acetyloxy)-N-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 39  0  0  0  0  0  0  0  0999 V2000
    5.7136    1.8180    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584    1.1380    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -0.1129   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6932   -0.7000   -0.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560   -0.7749   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059   -1.7659    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324   -2.4342   -0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7061   -1.3817   -0.3285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -0.6041    0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8094   -0.8575    1.9068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743    0.4286    0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.9327   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505    0.5189   -1.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247    2.0674    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7051    1.5960   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083    0.4091    0.5627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439   -0.2106    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5539   -1.4521    1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0662    0.2997   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3724    2.6078    1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1873    2.3194   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4131    1.1085    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.0722   -1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -1.3052   -1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582   -1.2339    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8080   -2.5392    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940   -3.1659    0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -2.9323   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370   -1.2734   -1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8624    0.9150    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    0.6503   -2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137    1.2503   -2.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162   -0.5004   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.3049    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    2.9325   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4843    2.3285    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789    1.3584   -1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3585   -2.3285    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6332   -1.4106    1.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9284   -1.4304    2.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv1533004161509462D          

 19 18  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  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
  9 10  2  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCCNC(=O)C=C(C)CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO5/c1-10(6-8-19-11(2)15)9-12(16)14-7-4-5-13(17)18-3/h9H,4-8H2,1-3H3,(H,14,16)

> <INCHI_KEY>
YJAKSKSMUOXRHW-UHFFFAOYSA-N

> <FORMULA>
C13H21NO5

> <MOLECULAR_WEIGHT>
271.313

> <EXACT_MASS>
271.14197278

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.281099364727268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-[5-(acetyloxy)-3-methylpent-2-enamido]butanoate

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
0.17824377533333363

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.675769852689601

> <JCHEM_PKA_STRONGEST_BASIC>
-0.11782245525429913

> <JCHEM_POLAR_SURFACE_AREA>
81.69999999999999

> <JCHEM_REFRACTIVITY>
69.95510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-[5-(acetyloxy)-3-methylpent-2-enamido]butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.264   6.311   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      13.598   4.771   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.599   2.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.267   4.001   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      21.600   4.771   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.934   4.001   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      24.268   4.771   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      22.934   2.461   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-N-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidate	Generator

Chemical Formula

C₁₃H₂₁NO₅

Average Mass

271.3130 Da

Monoisotopic Mass

271.14197 Da

IUPAC Name

methyl 4-[5-(acetyloxy)-3-methylpent-2-enamido]butanoate

Traditional Name

methyl 4-[5-(acetyloxy)-3-methylpent-2-enamido]butanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CCCNC(=O)C=C(C)CCOC(C)=O

InChI Identifier

InChI=1S/C13H21NO5/c1-10(6-8-19-11(2)15)9-12(16)14-7-4-5-13(17)18-3/h9H,4-8H2,1-3H3,(H,14,16)

InChI Key

YJAKSKSMUOXRHW-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma 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

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Fatty acid ester
Fatty acid methyl ester
Dicarboxylic acid or derivatives
Fatty acyl
Methyl ester
Carboxylic acid ester
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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
logP	1.11	ALOGPS
logP	0.18	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.68	ChemAxon
pKa (Strongest Basic)	-0.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.7 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	69.96 m³·mol⁻¹	ChemAxon
Polarizability	29.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75954492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid (NP0197586)

MOL for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

3D MOL for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

3D SDF for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

3D-SDF for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

PDB for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

3D PDB for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

SMILES for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

INCHI for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

Structure for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)

3D Structure for NP0197586 (5-(acetyloxy)-n-(4-methoxy-4-oxobutyl)-3-methylpent-2-enimidic acid)