NP-MRD: Showing NP-Card for 6-keto stearic acid (NP0191521)

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Record Information

Version

2.0

Created at

2022-09-04 08:31:04 UTC

Updated at

2022-09-04 08:31:04 UTC

NP-MRD ID

NP0191521

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-keto stearic acid

Description

Lactarinic acid, also known as lactarinate, 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. 6-keto stearic acid is found in Lactarius hepaticus, Lactarius hirtipes, Lactarius theiogalus and Lactarius violascens. Lactarinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.7574   -0.5981    2.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6753   -0.1475    1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3526   -0.4950    1.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1814   -0.0957    0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2143   -0.7701   -0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556   -0.3661   -1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329   -0.7013   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068   -0.2675   -1.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088    1.2109   -1.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5527    1.5273   -2.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8909    1.1612   -2.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458    1.9083   -0.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4896    1.5231   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376    2.0406    0.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475    0.5546   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5972    0.2394   -0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3369   -0.3928    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6567   -0.6949    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3763   -1.3227    2.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3067   -1.6702    3.7647 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895   -1.5489    3.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9505   -1.6865    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4208   -0.4834    3.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7196   -0.0801    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8626   -0.6726    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8038    0.9573    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927    0.0335    2.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3613   -1.5778    1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2405    0.9936    0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -0.2955    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -1.8808   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1713   -0.4895   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    0.7143   -1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -0.8930   -2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -1.8222   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -0.2629    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3358   -0.4834   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -0.8672   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.5592   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5112    1.8151   -0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438    0.9653   -3.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    2.6123   -3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    1.4960   -2.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    0.0765   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105    1.6525   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937    2.9790   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5439    0.9673   -2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264   -0.3640   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098    1.1562   -0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -0.4405   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008    0.1984    1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321   -1.3773    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1651    0.2906    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3123   -1.3273    1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353   -2.4025    3.7952 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  2  0
 13 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
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 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

  Mrv1533004231515192D          

 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
   13.4724    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
   14.9013    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
   16.3302    6.1283    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
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.9533    0.0000 O   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
   19.1881    6.1283    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
   20.6171    6.1283    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
   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
  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  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 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
M  END
> <DATABASE_ID>
NP0191521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC(=O)CCCCC(O)=O

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

> <INCHI_KEY>
QZLYZQUYIQGGOQ-UHFFFAOYSA-N

> <FORMULA>
C18H34O3

> <MOLECULAR_WEIGHT>
298.467

> <EXACT_MASS>
298.250794955

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.447945579735645

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-oxooctadecanoic acid

> <ALOGPS_LOGP>
6.03

> <JCHEM_LOGP>
5.966502382333333

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.550447242573036

> <JCHEM_PKA_STRONGEST_BASIC>
-7.346986901108872

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
86.92699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-keto stearic acid

> <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      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      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.483  11.439   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      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      33.150  12.979   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+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    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   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   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

Value	Source
Lactarinate	Generator
6-Oxooctadecanoate	Generator

Chemical Formula

C₁₈H₃₄O₃

Average Mass

298.4670 Da

Monoisotopic Mass

298.25079 Da

IUPAC Name

6-oxooctadecanoic acid

Traditional Name

6-keto stearic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC(=O)CCCCC(O)=O

InChI Identifier

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

InChI Key

QZLYZQUYIQGGOQ-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
Lactarius hepaticus	LOTUS Database	35616633
Lactarius hirtipes	LOTUS Database	35616633
Lactarius theiogalus	LOTUS Database	35616633
Lactarius violascens	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
Keto 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 (LMFA02000243 )

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	6.03	ALOGPS
logP	5.97	ChemAxon
logS	-5.5	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	38.45 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

361939

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-keto stearic acid (NP0191521)

MOL for NP0191521 (6-keto stearic acid)

3D MOL for NP0191521 (6-keto stearic acid)

3D SDF for NP0191521 (6-keto stearic acid)

3D-SDF for NP0191521 (6-keto stearic acid)

PDB for NP0191521 (6-keto stearic acid)

3D PDB for NP0191521 (6-keto stearic acid)

SMILES for NP0191521 (6-keto stearic acid)

INCHI for NP0191521 (6-keto stearic acid)

Structure for NP0191521 (6-keto stearic acid)

3D Structure for NP0191521 (6-keto stearic acid)