NP-MRD: Showing NP-Card for 9-keto stearic acid (NP0283299)

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Record Information

Version

2.0

Created at

2022-09-09 10:30:21 UTC

Updated at

2022-09-09 10:30:22 UTC

NP-MRD ID

NP0283299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-keto stearic acid

Description

9-Oxooctadecanoic acid, also known as 9-keto stearic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 9-Oxooctadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 9-Oxooctadecanoic acid has been detected, but not quantified in, milk and milk products. 9-keto stearic acid is found in Galeopsis bifida. This could make 9-oxooctadecanoic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 54  0  0  0  0  0  0  0  0999 V2000
   -4.8844   -2.3995    1.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601   -2.7170   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572   -1.4378   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670   -0.4764   -1.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9653    0.8281   -1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0823    1.8387   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6447    1.5268   -0.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292    2.8128   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    2.7121   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799    1.6994    0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290    0.8794    1.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    1.6209    1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.1912    0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981    1.0436    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6799   -0.0388    1.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602   -0.1663    1.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9379   -0.4685    0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -1.7149   -0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7082   -2.8977    0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1682   -2.8519    1.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3609   -4.1886    0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467   -1.8718    1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0289   -3.3701    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454   -1.8809    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2566   -3.2516   -0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -3.3378   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848   -1.1235   -0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -1.8272   -2.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4399   -0.2254   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1101   -0.9417   -1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7432    0.6923   -2.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0118    1.3131   -1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4896    2.1668   -0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0935    2.8114   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861    1.1597   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535    0.7929   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718    3.5789   -1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    3.1035    0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    3.7097    0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059    2.5187   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086    2.5996    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    0.8580    2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    0.1889   -0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763    1.8783   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8362    2.0117    0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.8632   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -0.9757    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    0.2065    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3421   -0.8607    2.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4698    0.8409    2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0179    0.4129   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0068   -0.6220    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4343   -1.7120   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0735   -1.8156   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9854   -4.6868   -0.3514 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  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
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
M  END


  Mrv0541 05061305382D          

 21 20  0  0  0  0            999 V2000
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC(=O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h2-16H2,1H3,(H,20,21)

> <INCHI_KEY>
KNYQSFOUGYMRDE-UHFFFAOYSA-N

> <FORMULA>
C18H34O3

> <MOLECULAR_WEIGHT>
298.4608

> <EXACT_MASS>
298.250794954

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.26132045810559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-oxooctadecanoic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.966502382333333

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.550449811137081

> <JCHEM_PKA_STRONGEST_BASIC>
-7.346983285910296

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
86.92699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-keto stearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.151  11.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      29.149   9.129   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      39.819   9.129   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    8                                                       
CONECT    7    9   10                                                       
CONECT    8    6   11                                                       
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   19                                                  
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
9-Oxooctadecanoate	Generator
9-Keto stearic acid	HMDB
9-Ketostearic acid	HMDB
9-oxo-Octadecanoic acid	HMDB
9-Oxostearic acid	HMDB
9-Keto stearate	Generator

Chemical Formula

C₁₈H₃₄O₃

Average Mass

298.4608 Da

Monoisotopic Mass

298.25079 Da

IUPAC Name

9-oxooctadecanoic acid

Traditional Name

9-keto stearic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC(=O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h2-16H2,1H3,(H,20,21)

InChI Key

KNYQSFOUGYMRDE-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
Galeopsis bifida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000245 )

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	5.88	ALOGPS
logP	5.97	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	-7.3	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	16	ChemAxon
Refractivity	86.93 m³·mol⁻¹	ChemAxon
Polarizability	38.26 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

HMDB0030979

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002967

KNApSAcK ID

Not Available

Chemspider ID

2340980

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083831

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-keto stearic acid (NP0283299)

MOL for NP0283299 (9-keto stearic acid)

3D MOL for NP0283299 (9-keto stearic acid)

3D SDF for NP0283299 (9-keto stearic acid)

3D-SDF for NP0283299 (9-keto stearic acid)

PDB for NP0283299 (9-keto stearic acid)

3D PDB for NP0283299 (9-keto stearic acid)

SMILES for NP0283299 (9-keto stearic acid)

INCHI for NP0283299 (9-keto stearic acid)

Structure for NP0283299 (9-keto stearic acid)

3D Structure for NP0283299 (9-keto stearic acid)