Cannabis Compound Database: Showing Compound Card for Pelargonic acid (CDB000383)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8)transporters (1) Show 17 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:34:10 UTC

Updated at

2020-12-07 19:07:24 UTC

CannabisDB ID

CDB000383

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Pelargonic acid

Description

Pelargonic acid, also known as nonanoic acid or pelargon, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Pelargonic acid is an oily liquid with an unpleasant, rancid odor. It is a very hydrophobic molecule, practically insoluble in water but very soluble in organic solvents. The biosynthesis of fatty acid occurs through the acetate pathway and the process is catalyzed by the Fatty Acid Synthase (FAS) enzymes. Structurally, FAS varies significantly across different organisms but essentially, they all perform the same task using the same mechanisms. Pelargonic acid is one of the saturated fatty acids that have been identified in cannabis plant (PMID: 661645 ).¬† Nonanoic acid is also used in the preparation of plasticizers and lacquers. Synthetic esters of nonanoic acid, such as methyl nonanoate, are used as flavorings. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays. The ammonium salt of nonanoic acid, ammonium nonanoate, is an herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, to control weeds in turfgrass ( Ref:DOI ). Nonanoic acid may be used to treat seizures (PMID 23177536 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Nonanoic acid	ChEBI
1-Octanecarboxylic acid	ChEBI
CH3-[CH2]7-COOH	ChEBI
N-Nonanoic acid	ChEBI
Nonanoate	ChEBI
Nonansaeure	ChEBI
Nonoic acid	ChEBI
Nonylic acid	ChEBI
Pelargic acid	ChEBI
Pelargon	ChEBI
Pelargonsaeure	ChEBI
Pergonic acid	ChEBI
1-Nonanoate	Generator
1-Octanecarboxylate	Generator
N-Nonanoate	Generator
Nonanoic acid	Generator
Nonoate	Generator
Nonylate	Generator
Pelargate	Generator
Pergonate	Generator
Pelargonate	Generator
Cirrasol 185a	HMDB
Emery 1202	HMDB
Emery'S L-114	HMDB
Emfac 1202	HMDB
Hexacid C-9	HMDB
N-Nonoate	HMDB
N-Nonoic acid	HMDB
N-Nonylate	HMDB
N-Nonylic acid	HMDB
N-Pelargonate	HMDB
N-Pelargonic acid	HMDB
Pelargonic acid, calcium salt	HMDB
Potassium nonanoate	HMDB
Pelargonic acid, cadmium salt	HMDB
Pelargonic acid, sodium salt	HMDB
Pelargonic acid, zinc salt	HMDB
Pelargonic acid, aluminum salt	HMDB
Pelargonic acid, potassium salt	HMDB
FA(9:0)	HMDB
Pelargonic acid	ChEBI

Chemical Formula

C₉H₁₈O₂

Average Molecular Weight

158.24

Monoisotopic Molecular Weight

158.1307

IUPAC Name

nonanoic acid

Traditional Name

nonanoic acid

CAS Registry Number

112-05-0

SMILES

CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)

InChI Key

FBUKVWPVBMHYJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain 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

medium-chain fatty acid (CHEBI:29019 )
straight-chain saturated fatty acid (CHEBI:29019 )
Straight chain fatty acids (C01601 )
Straight chain fatty acids (LMFA01010009 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Epidermis

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	12.3 °C	Not Available
Boiling Point	254 °C	Wikipedia
Water Solubility	0.28 mg/mL	Not Available
logP	3.42	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	3.47	ALOGPS
logP	3.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.23	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	7	ChemAxon
Refractivity	44.88 m³·mol⁻¹	ChemAxon
Polarizability	19.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-08ml-9000000000-e02b73fd7a397aa0b40b	2014-09-20	View Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0910000000-29827f2f9240f991b625	Spectrum
GC-MS	Pelargonic acid, 1 TMS, GC-MS Spectrum	splash10-014i-2920000000-8730f6690cd20a58fcfc	Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-03di-9200000000-0842bd1d3fcea3f9f005	Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-08ml-9000000000-f9b45b786372be8b75d6	Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0930000000-30578d3edfa20cedf0e8	Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0910000000-29827f2f9240f991b625	Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-014i-2920000000-8730f6690cd20a58fcfc	Spectrum
GC-MS	Pelargonic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0910000000-2e292fa3a6e414ce582a	Spectrum
Predicted GC-MS	Pelargonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-059f-9100000000-aaba2a9436e55f8d4c46	Spectrum
Predicted GC-MS	Pelargonic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06du-9200000000-bffc58a95ef321200ab9	Spectrum
Predicted GC-MS	Pelargonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pelargonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pelargonic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0k9l-9400000000-fb4f24d4e9b0b4685763	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-a3d26c56923a3cdddf9c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-a6e0c758ef2e822a5d73	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-03di-9200000000-0842bd1d3fcea3f9f005	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-08ml-9000000000-141c2435131c4b235390	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0900000000-2ea046a2e7b029c3cd81	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-0900000000-1efff6d47779ec04f434	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-6900000000-bcf3e35c2fbd86e670f0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-056r-9000000000-9c72ae1d7f8e978ec7f8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-c052a9b360e11f6a6eb9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-2ea046a2e7b029c3cd81	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-1efff6d47779ec04f434	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-6900000000-bcf3e35c2fbd86e670f0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-056r-9000000000-9c72ae1d7f8e978ec7f8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c052a9b360e11f6a6eb9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0a4i-0900000000-b56762cc671f243abe6f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9000000000-ae54c10a9e1b7264831e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9500000000-65dcbde71c36004a3676	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8ddcc5d65e84f9048b88	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-2b95d53127d2c88c6b0c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06r6-6900000000-e3f666b3dcf9b3b1c2fe	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-8432ab96716adadb8d13	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-32f3915adea9c27b0b74	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1900000000-2ffdf4f1d36a54e86be1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-647e33e0c7198b77f78b	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Fatty acid synthase	FASN	17q25	P49327	details
Acyl-coenzyme A synthetase ACSM1, mitochondrial	ACSM1	16p12.3	Q08AH1	details
Acyl-coenzyme A synthetase ACSM6, mitochondrial	ACSM6	10q23.33	Q6P461	details
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	ACSM2A	16p12.3	Q08AH3	details
Acyl-coenzyme A synthetase ACSM2B, mitochondrial	ACSM2B	16p12.3	Q68CK6	details
Acyl-coenzyme A synthetase ACSM3, mitochondrial	ACSM3	16p13.11	Q53FZ2	details
Acyl-coenzyme A synthetase ACSM5, mitochondrial	ACSM5	16p12.3	Q6NUN0	details
Acyl-coenzyme A synthetase ACSM4, mitochondrial	ACSM4	12p13.31	P0C7M7	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Fatty acid synthase	FASN	17q25	P49327	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Fatty acid synthase	FASN	17q25	P49327	details
Acyl-coenzyme A synthetase ACSM1, mitochondrial	ACSM1	16p12.3	Q08AH1	details
Acyl-coenzyme A synthetase ACSM6, mitochondrial	ACSM6	10q23.33	Q6P461	details
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	ACSM2A	16p12.3	Q08AH3	details
Acyl-coenzyme A synthetase ACSM2B, mitochondrial	ACSM2B	16p12.3	Q68CK6	details
Acyl-coenzyme A synthetase ACSM3, mitochondrial	ACSM3	16p13.11	Q53FZ2	details
Acyl-coenzyme A synthetase ACSM5, mitochondrial	ACSM5	16p12.3	Q6NUN0	details
Acyl-coenzyme A synthetase ACSM4, mitochondrial	ACSM4	12p13.31	P0C7M7	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000847

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Nonanoic_acid

METLIN ID

5810

PubChem Compound

8158

PDB ID

Not Available

ChEBI ID

29019

References

General References

Miller IuM, Marchenko IV, Kapustin OA, Galanina LA, Bekhtereva MN: [Use of a mass spectrometric method for studying the oxygen demand of suspensions of resting Bacillus anthracoides spores]. Mikrobiologiia. 1978 Mar-Apr;47(2):357-61. [PubMed:661645 ]
Chang P, Terbach N, Plant N, Chen PE, Walker MC, Williams RS: Seizure control by ketogenic diet-associated medium chain fatty acids. Neuropharmacology. 2013 Jun;69:105-14. doi: 10.1016/j.neuropharm.2012.11.004. Epub 2012 Nov 20. [PubMed:23177536 ]

Only showing the first 10 proteins. There are 17 proteins in total.

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Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Enzyme Details

2. Acyl-coenzyme A synthetase ACSM1, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:: ACSM1
Uniprot ID:: Q08AH1
Molecular weight:: 65272.74

Enzyme Details

3. Acyl-coenzyme A synthetase ACSM6, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ACSM6
Uniprot ID:: Q6P461
Molecular weight:: 53584.545

Enzyme Details

4. Acyl-coenzyme A synthetase ACSM2A, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM2A
Uniprot ID:: Q08AH3
Molecular weight:: 64223.7

Enzyme Details

5. Acyl-coenzyme A synthetase ACSM2B, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:: ACSM2B
Uniprot ID:: Q68CK6
Molecular weight:: 64270.78

Enzyme Details

6. Acyl-coenzyme A synthetase ACSM3, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM3
Uniprot ID:: Q53FZ2
Molecular weight:: 66152.235

Enzyme Details

7. Acyl-coenzyme A synthetase ACSM5, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM5
Uniprot ID:: Q6NUN0
Molecular weight:: 64759.55

Enzyme Details

8. Acyl-coenzyme A synthetase ACSM4, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM4
Uniprot ID:: P0C7M7
Molecular weight:: 65702.225

Transporters

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Only showing the first 10 proteins. There are 17 proteins in total.

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Showing Compound Card for Pelargonic acid (CDB000383)

Structure for CDB000383 (Pelargonic acid)

Enzymes

Transporters