NP-MRD: Showing NP-Card for Petroselinic acid (NP0000010)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:35 UTC

Updated at

2024-09-03 04:18:16 UTC

NP-MRD ID

NP0000010

Natural Product DOI

https://doi.org/10.57994/1340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Petroselinic acid

Description

Petroselinic acid, also known as (6Z)-Octadecenoic acid, is an 18-carbon unsaturated fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated as 18:1 Cis-6. Petroselinic acid is a positional isomer of oleic acid. The term "petroselinic" means related to, or derived from, oil of Petroselinum, or oil of parsley. Petroselinic acid was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in the Apiaceae family (a family of mostly aromatic flowering plants named after the genus Apium and commonly known as the celery, carrot or parsley family), Araliaceae (a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants), Griselinia (Griseliniaceae) and in Garryaceae. The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales. Petroselonic acid has been found in coriander (Coriandrum sativum) and cumin (Cuminum cyminum) and caraway seeds. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical industry (PMID: 16604360 ) As it can be easily processed into lauric and adipinic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305201900032D          

 20 19  0  0  0  0            999 V2000
    3.5211    2.8579    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
    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
   10.6658    2.8579    0.0000 C   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
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    6.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    5.3329    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
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 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  2  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC=CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)

> <INCHI_KEY>
CNVZJPUDSLNTQU-UHFFFAOYSA-N

> <FORMULA>
C18H34O2

> <MOLECULAR_WEIGHT>
282.468

> <EXACT_MASS>
282.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.641961416794885

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octadec-6-enoic acid

> <ALOGPS_LOGP>
7.72

> <JCHEM_LOGP>
6.783798451000001

> <ALOGPS_LOGS>
-6.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885821319747302

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.4022

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-octadecenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       6.573   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.911   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.911   7.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.244   8.415   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.244   9.955   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.578  10.725   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      26.578  12.265   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      27.912   9.955   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                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
18:1N-6	ChEBI
6-Octadecensaeure	ChEBI
C18:1N-6	ChEBI
Octadec-6-ensaeure	ChEBI
Petroselinate	Generator
Octadec-6-enoate	HMDB
Petroselinic acid, (e)-isomer	HMDB
Petroselinic acid, sodium salt, (Z)-isomer	HMDB
Petroselenic acid	HMDB
Petroselinic acid, (Z)-isomer	HMDB
Petroselinic acid	MeSH

Chemical Formula

C₁₈H₃₄O₂

Average Mass

282.4680 Da

Monoisotopic Mass

282.25588 Da

IUPAC Name

octadec-6-enoic acid

Traditional Name

6-octadecenoic acid

CAS Registry Number

593-39-5

SMILES

CCCCCCCCCCCC=CCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)

InChI Key

CNVZJPUDSLNTQU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Agaricus blazei		LOTUS database
Anas platyrhynchos		FooDB
Anatidae		FooDB
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anser anser		FooDB
Anthriscus cerefolium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aralia spinosa	KNApSAcK Database	22123792
Bison bison		FooDB
Bos taurus		FooDB
Bos taurus X Bison bison		FooDB
Bubalus bubalis		FooDB
Bupleurum chinense	KNApSAcK Database	22123792
Capra aegagrus hircus		FooDB
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cervidae		FooDB
Cervus canadensis		FooDB
Chlamydomonas reinhardtii		LOTUS database
Columba		FooDB
Columbidae		FooDB
Coriandrum sativum		LOTUS database
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cuminum cyminum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dromaius novaehollandiae		FooDB
Eleutherococcus sessiliflorus		LOTUS database
Equus caballus		FooDB
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gallus gallus		FooDB
Heracleum sphondylium		LOTUS database
Hibiscus syriacus		LOTUS database
Lagopus muta		FooDB
Leporidae		FooDB
Lepus timidus		FooDB
Macrococculus pomiferus		LOTUS database
Melanitta fusca		FooDB
Meleagris gallopavo		FooDB
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Myristica fragrans		LOTUS database
Myrrhis odorata		LOTUS database
Nepeta cataria		LOTUS database
Numida meleagris		FooDB
Odocoileus		FooDB
Oryctolagus		FooDB
Ovis aries		FooDB
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petroselinum crispum	KNApSAcK Database	22123792
Phasianidae		FooDB
Phasianus colchicus		FooDB
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Struthio camelus		FooDB
Sus scrofa		FooDB
Sus scrofa domestica		FooDB
Teucrium royleanum		LOTUS database
Thapsia villosa		LOTUS database
Tritrichomonas foetus		LOTUS database

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
Unsaturated fatty acid
Straight chain fatty acid
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

octadecenoic acid (CHEBI:36022 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	29.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.9e-05 g/L	ALOGPS
logP	7.72	ALOGPS
logP	6.78	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	87.4 m³·mol⁻¹	ChemAxon
Polarizability	37.64 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

HMDB0002080

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012765

KNApSAcK ID

C00001235

Chemspider ID

11144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Petroselinic acid

METLIN ID

Not Available

PubChem Compound

11634

PDB ID

Not Available

ChEBI ID

36022

Good Scents ID

Not Available

References

General References

Metzger JO, Bornscheuer U: Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol. 2006 Jun;71(1):13-22. Epub 2006 Apr 8. [PubMed:16604360 ]
Ping F, Li Y, Cao Y, Shang J, Zhang Z, Yuan Z, Wang W, Guo Y: Metabolomics Analysis of the Development of Sepsis and Potential Biomarkers of Sepsis-Induced Acute Kidney Injury. Oxid Med Cell Longev. 2021 Apr 23;2021:6628847. doi: 10.1155/2021/6628847. eCollection 2021. [PubMed:33981387 ]
Saini RK, Assefa AD, Keum YS: Spices in the Apiaceae Family Represent the Healthiest Fatty Acid Profile: A Systematic Comparison of 34 Widely Used Spices and Herbs. Foods. 2021 Apr 14;10(4). pii: foods10040854. doi: 10.3390/foods10040854. [PubMed:33920058 ]
Erbiai EH, da Silva LP, Saidi R, Lamrani Z, Esteves da Silva JCG, Maouni A: Chemical Composition, Bioactive Compounds, and Antioxidant Activity of Two Wild Edible Mushrooms Armillaria mellea and Macrolepiota procera from Two Countries (Morocco and Portugal). Biomolecules. 2021 Apr 14;11(4). pii: biom11040575. doi: 10.3390/biom11040575. [PubMed:33920034 ]

Showing NP-Card for Petroselinic acid (NP0000010)

MOL for NP0000010 (Petroselinic acid)

3D MOL for NP0000010 (Petroselinic acid)

3D SDF for NP0000010 (Petroselinic acid)

3D-SDF for NP0000010 (Petroselinic acid)

PDB for NP0000010 (Petroselinic acid)

3D PDB for NP0000010 (Petroselinic acid)

SMILES for NP0000010 (Petroselinic acid)

INCHI for NP0000010 (Petroselinic acid)

Structure for NP0000010 (Petroselinic acid)

3D Structure for NP0000010 (Petroselinic acid)