NP-MRD: Showing NP-Card for 13(S)-Hydroperoxylinolenic acid (NP0045553)

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Record Information

Version

2.0

Created at

2022-03-17 19:31:44 UTC

Updated at

2022-03-17 19:31:44 UTC

NP-MRD ID

NP0045553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13(S)-Hydroperoxylinolenic acid

Description

13(S)-Hydroperoxylinolenic acid, also known as 13(S)-hpotre or 13-HPOT, 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. 13(S)-Hydroperoxylinolenic acid is found in Arabidopsis thaliana, Glycine max , Lyngbya majuscula and Skeletonema marinoi. 13(S)-Hydroperoxylinolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241221382D          

 22 21  0  0  1  0            999 V2000
    2.2836   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -5.0309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2849   -5.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -6.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/b9-7-,11-3-,15-12+/t17-/m0/s1

> <INCHI_KEY>
UYQGVDXDXBAABN-FQSPHKRJSA-N

> <FORMULA>
C18H30O4

> <MOLECULAR_WEIGHT>
310.4284

> <EXACT_MASS>
310.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.77882266536244

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
5.278479448

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.711074282435678

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167201738501

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144817387

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
92.5011

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13(S)-HpOTrE

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.263  -4.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.596  -4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596  -6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931  -4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.266  -4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.266  -6.311   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.932  -7.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.932  -8.621   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.598  -9.391   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.598 -10.931   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.932 -11.701   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.265  -8.621   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.265  -7.081   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.931  -6.311   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.597  -7.081   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.597  -8.621   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoic acid	ChEBI
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoate	ChEBI
13(S)-HPOT	ChEBI
13(S)-HpOTrE	ChEBI
13(S)-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoic acid	ChEBI
13-HPOT	ChEBI
13S-HpOTrE	ChEBI
13S-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoic acid	ChEBI
13S-Hydroperoxy-9Z,11E,15Z-octadecatrienoic acid	ChEBI
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoate	Generator
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoic acid	Generator
13(S)-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoate	Generator
13S-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoate	Generator
13S-Hydroperoxy-9Z,11E,15Z-octadecatrienoate	Generator
13(S)-Hydroperoxylinolenate	Generator
13(S)-Hydroperoxylinolenic acid	ChEBI
13-Hydroperoxy-9,11,15-octadecatrienoic acid	MeSH

Chemical Formula

C₁₈H₃₀O₄

Average Mass

310.4284 Da

Monoisotopic Mass

310.21441 Da

IUPAC Name

(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid

Traditional Name

13(S)-HpOTrE

CAS Registry Number

67597-26-6

SMILES

CC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/b9-7-,11-3-,15-12+/t17-/m0/s1

InChI Key

UYQGVDXDXBAABN-FQSPHKRJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Arabidopsis thaliana	Plant	KNApSAcK
Glycine max	Plant	KNApSAcK
Lyngbya majuscula	-	KNApSAcK
Skeletonema marinoi	LOTUS Database	35616633
Zea mays L.	FooDB	KNAPSACK

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
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Carboxylic acid
Peroxol
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:48905 )
lipid hydroperoxide (CHEBI:48905 )
trienoic fatty acid (CHEBI:48905 )
Hydroperoxy fatty acids (C04785 )
Other Octadecanoids (LMFA02000052 )

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	5.46	ALOGPS
logP	5.28	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	92.5 m³·mol⁻¹	ChemAxon
Polarizability	36.78 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

FDB001431

KNApSAcK ID

C00000364

Chemspider ID

Not Available

KEGG Compound ID

C04785

BioCyc ID

CPD-725

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497123

PDB ID

Not Available

ChEBI ID

48905

Good Scents ID

Not Available

References

General References

Showing NP-Card for 13(S)-Hydroperoxylinolenic acid (NP0045553)

MOL for NP0045553 (13(S)-Hydroperoxylinolenic acid)

3D MOL for NP0045553 (13(S)-Hydroperoxylinolenic acid)

3D SDF for NP0045553 (13(S)-Hydroperoxylinolenic acid)

3D-SDF for NP0045553 (13(S)-Hydroperoxylinolenic acid)

PDB for NP0045553 (13(S)-Hydroperoxylinolenic acid)

3D PDB for NP0045553 (13(S)-Hydroperoxylinolenic acid)

SMILES for NP0045553 (13(S)-Hydroperoxylinolenic acid)

INCHI for NP0045553 (13(S)-Hydroperoxylinolenic acid)

Structure for NP0045553 (13(S)-Hydroperoxylinolenic acid)

3D Structure for NP0045553 (13(S)-Hydroperoxylinolenic acid)