NP-MRD: Showing NP-Card for 4-oxooctadec-2-enoic acid (NP0288805)

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Record Information

Version

2.0

Created at

2022-09-09 18:40:57 UTC

Updated at

2022-09-09 18:40:57 UTC

NP-MRD ID

NP0288805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-oxooctadec-2-enoic acid

Description

21436-59-9 Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. 4-oxooctadec-2-enoic acid is found in Hygrophorus eburneus. 21436-59-9 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 52  0  0  0  0  0  0  0  0999 V2000
   -5.0040   -1.6014    2.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4569   -1.1618    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4572   -0.2064    0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2657    0.3844   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1132    1.2318   -0.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.6866   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4893   -0.5182   -1.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1038   -1.0818   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -0.0563   -1.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192   -0.5975   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2712    0.4724   -2.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    1.6783   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4086    1.3408    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8577    0.7819    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1310    0.4702    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468    0.7292    2.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -0.0678    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4307   -0.4356    1.6911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9968   -0.4650    0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4462   -0.0998   -0.6432 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3196   -0.9483    0.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -2.4193    3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8420   -0.7385    3.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595   -1.9004    2.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529   -2.0885    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673   -0.7530    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629   -0.7420    0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5477    0.6111    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1931    1.0334   -0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3621   -0.3738   -1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133    2.1737   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2473    1.6100   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0864    1.5178   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609    0.6598    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956   -1.3213   -1.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -0.3367   -2.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360   -1.9687   -2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294   -1.4693   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    0.8103   -1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2882    0.2541   -2.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -1.4910   -2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -0.9828   -0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139    0.1257   -2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285    0.8004   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8954    2.4681   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1599    2.1934   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352    2.2321    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7040    0.5978    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261    1.5514   -0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8803   -0.1248   -0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2299   -0.2078    3.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1427   -0.8299    2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7822   -1.4269    0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 17 51  1  0
 18 52  1  0
 21 53  1  0
M  END


  Mrv1533004261513532D          

 21 20  0  0  0  0            999 V2000
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565    4.2868    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  1  0  0  0  0
  9 10  1  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  2  0  0  0  0
 17 15  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCC(=O)C=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(19)15-16-18(20)21/h15-16H,2-14H2,1H3,(H,20,21)

> <INCHI_KEY>
DOCHQQOWHPNKAZ-UHFFFAOYSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.54432758547328

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-oxooctadec-2-enoic acid

> <ALOGPS_LOGP>
6.32

> <JCHEM_LOGP>
6.324071018333333

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.495758661551099

> <JCHEM_PKA_STRONGEST_BASIC>
-7.000531177998897

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
87.99699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxooctadec-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      11.193   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.530   8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      29.864   6.462   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      31.198   8.772   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.532   8.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.865   8.772   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      33.865  10.312   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      35.199   8.002   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                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4510 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

4-oxooctadec-2-enoic acid

Traditional Name

4-oxooctadec-2-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC(=O)C=CC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(19)15-16-18(20)21/h15-16H,2-14H2,1H3,(H,20,21)

InChI Key

DOCHQQOWHPNKAZ-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

Species Name	Source	Reference
Hygrophorus eburneus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Keto fatty acid
Fatty acid
Unsaturated fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	6.32	ALOGPS
logP	6.32	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	88 m³·mol⁻¹	ChemAxon
Polarizability	37.54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71357058

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-oxooctadec-2-enoic acid (NP0288805)

MOL for NP0288805 (4-oxooctadec-2-enoic acid)

3D MOL for NP0288805 (4-oxooctadec-2-enoic acid)

3D SDF for NP0288805 (4-oxooctadec-2-enoic acid)

3D-SDF for NP0288805 (4-oxooctadec-2-enoic acid)

PDB for NP0288805 (4-oxooctadec-2-enoic acid)

3D PDB for NP0288805 (4-oxooctadec-2-enoic acid)

SMILES for NP0288805 (4-oxooctadec-2-enoic acid)

INCHI for NP0288805 (4-oxooctadec-2-enoic acid)

Structure for NP0288805 (4-oxooctadec-2-enoic acid)

3D Structure for NP0288805 (4-oxooctadec-2-enoic acid)