NP-MRD: Showing NP-Card for 1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one (NP0226067)

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Record Information

Version

2.0

Created at

2022-09-06 04:59:24 UTC

Updated at

2022-09-06 04:59:24 UTC

NP-MRD ID

NP0226067

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one

Description

1-Acetyl-5-ethylidene-4-hydroxy-3-octanoyl-2,5-dihydro-1H-pyrrol-2-one belongs to the class of organic compounds known as n-substituted carboxylic acid imides. N-substituted carboxylic acid imides are compounds comprising an N-substituted carboxylic acid imide group, with the general structure R1N(C(R2)=O)C(R3)=O (R2,R3=H, alkyl, aryl; R1=Anything but H). 1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one is found in Vibrio gazogenes. 1-Acetyl-5-ethylidene-4-hydroxy-3-octanoyl-2,5-dihydro-1H-pyrrol-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241511502D          

 21 21  0  0  0  0            999 V2000
    3.5108   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9398   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -3.0830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1518   -3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -4.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3528   -4.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6883   -3.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1198   -5.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4554   -6.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9704   -6.7336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2758   -6.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3128   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6997   -5.6930    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 13 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
 16 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226067

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)C1=C(O)C(=CC)N(C(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO4/c1-4-6-7-8-9-10-13(19)14-15(20)12(5-2)17(11(3)18)16(14)21/h5,20H,4,6-10H2,1-3H3

> <INCHI_KEY>
KVUSAHYINQEOIX-UHFFFAOYSA-N

> <FORMULA>
C16H23NO4

> <MOLECULAR_WEIGHT>
293.363

> <EXACT_MASS>
293.162708225

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.00657592498936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-acetyl-5-ethylidene-4-hydroxy-3-octanoyl-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.3389716576666673

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.839031527786787

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.927834978461807

> <JCHEM_PKA_STRONGEST_BASIC>
-6.416724980569868

> <JCHEM_POLAR_SURFACE_AREA>
74.68

> <JCHEM_REFRACTIVITY>
82.3489

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.554  -8.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.887  -7.295   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.221  -8.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.555  -7.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.888  -8.065   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.222  -7.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.556  -8.065   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.889  -7.295   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.889  -5.755   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      17.223  -8.065   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.630  -7.439   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.950  -5.932   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.660  -8.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.192  -8.422   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.818  -7.015   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      18.890  -9.917   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      19.517 -11.324   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.611 -12.569   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      21.048 -11.485   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.384  -9.597   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.239 -10.627   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   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   10   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₃NO₄

Average Mass

293.3630 Da

Monoisotopic Mass

293.16271 Da

IUPAC Name

1-acetyl-5-ethylidene-4-hydroxy-3-octanoyl-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)C1=C(O)C(=CC)N(C(C)=O)C1=O

InChI Identifier

InChI=1S/C16H23NO4/c1-4-6-7-8-9-10-13(19)14-15(20)12(5-2)17(11(3)18)16(14)21/h5,20H,4,6-10H2,1-3H3

InChI Key

KVUSAHYINQEOIX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vibrio gazogenes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-substituted carboxylic acid imides. N-substituted carboxylic acid imides are compounds comprising an N-substituted carboxylic acid imide group, with the general structure R1N(C(R2)=O)C(R3)=O (R2,R3=H, alkyl, aryl; R1=Anything but H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

N-substituted carboxylic acid imides

Alternative Parents

Substituents

Carboxylic acid imide, n-substituted
Dicarboximide
Pyrroline
Vinylogous acid
Acetamide
Ketone
Organoheterocyclic compound
Enol
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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
logP	3.18	ALOGPS
logP	2.34	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	82.35 m³·mol⁻¹	ChemAxon
Polarizability	33.01 Å³	ChemAxon
Number of Rings	1	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one (NP0226067)

MOL for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

3D MOL for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

3D SDF for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

3D-SDF for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

PDB for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

3D PDB for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

SMILES for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

INCHI for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

Structure for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)

3D Structure for NP0226067 (1-acetyl-5-ethylidene-4-hydroxy-3-octanoylpyrrol-2-one)