NP-MRD: Showing NP-Card for methyl 4-oxooctadeca-9,11,13-trienoate (NP0150659)

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Record Information

Version

1.0

Created at

2022-09-02 06:50:31 UTC

Updated at

2022-09-02 06:50:31 UTC

NP-MRD ID

NP0150659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-oxooctadeca-9,11,13-trienoate

Description

Methyl 4-oxooctadeca-9,11,13-trienoate 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. methyl 4-oxooctadeca-9,11,13-trienoate is found in Chrysobalanus icaco. Methyl 4-oxooctadeca-9,11,13-trienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.1732   -1.3075   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0267   -0.5363   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4337    0.6012    0.5059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3025    0.3789    1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0986   -0.1095    0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9701    0.6488    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684    0.3409    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    0.0656   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    0.8208   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    0.5161   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8146    1.4401   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0435    0.8013   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382   -0.2235   -1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -0.8313   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9401    0.2009   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5752    1.3679   -0.9350 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3485    0.0705   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700   -1.2881   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4234   -1.2371   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1471   -2.2414   -0.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0124    0.0038    0.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3741    0.1189    0.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8604   -1.6223   -2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8164   -2.2565   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3639   -0.7689   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8952   -0.0878   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5158   -1.2562    0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1890    1.4063   -0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2679    1.0601    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0697    1.3546    1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5649   -0.3006    2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0644   -1.0226    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837    1.5752    1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504    1.4124    0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.8942   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5069    1.7598    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -0.3953   -1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    1.8267   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    2.3122    0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    0.2433    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350    1.5566    0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7949   -1.0545   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282    0.2067   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -1.3628    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1465   -1.5191   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9679    0.8650   -0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4470    0.3090    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885   -1.5531   -1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4921   -2.0651    0.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0765   -0.0146   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6028   -0.5026    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4867    1.1873    0.9286 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  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  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
M  END


  Mrv1533004231520202D          

 22 21  0  0  0  0            999 V2000
    1.3776    9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    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  1  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  9  8  1  4  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  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  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
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC=CC=CC=CCCCCC(=O)CCC(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)16-17-19(21)22-2/h6-11H,3-5,12-17H2,1-2H3

> <INCHI_KEY>
BGHALTBJTYRCGM-UHFFFAOYSA-N

> <FORMULA>
C19H30O3

> <MOLECULAR_WEIGHT>
306.446

> <EXACT_MASS>
306.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.53685127022054

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-oxooctadeca-9,11,13-trienoate

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
5.026631468333333

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.38715486435236

> <JCHEM_PKA_STRONGEST_BASIC>
-6.861412886508056

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
95.04589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.21e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-oxooctadeca-9,11,13-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.572  16.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.572  15.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.905  14.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.905  13.035   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.239  12.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.239  10.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   9.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.575   3.795   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      19.909   5.335   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+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   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-oxooctadeca-9,11,13-trienoic acid	Generator

Chemical Formula

C₁₉H₃₀O₃

Average Mass

306.4460 Da

Monoisotopic Mass

306.21949 Da

IUPAC Name

methyl 4-oxooctadeca-9,11,13-trienoate

Traditional Name

methyl 4-oxooctadeca-9,11,13-trienoate

CAS Registry Number

Not Available

SMILES

CCCCC=CC=CC=CCCCCC(=O)CCC(=O)OC

InChI Identifier

InChI=1S/C19H30O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)16-17-19(21)22-2/h6-11H,3-5,12-17H2,1-2H3

InChI Key

BGHALTBJTYRCGM-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
Chrysobalanus icaco	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
Gamma-keto acid
Fatty acid ester
Fatty acid methyl ester
Keto acid
Methyl ester
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	5.38	ALOGPS
logP	5.03	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	17.39	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	95.05 m³·mol⁻¹	ChemAxon
Polarizability	38.54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

53680500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-oxooctadeca-9,11,13-trienoate (NP0150659)

MOL for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

3D MOL for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

3D SDF for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

3D-SDF for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

PDB for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

3D PDB for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

SMILES for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

INCHI for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

Structure for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)

3D Structure for NP0150659 (methyl 4-oxooctadeca-9,11,13-trienoate)