Cannabis Compound Database: Showing Compound Card for Dodecanoic acid (CDB004852)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9)transporters (2) Show 16 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:43:27 UTC

Updated at

2020-12-07 19:11:06 UTC

CannabisDB ID

CDB004852

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dodecanoic acid

Description

Dodecanoic acid also known as Lauric acid, 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. Lauric acid is a weakly acidic compound. It is a white, powdery solid with a faint odour of mild fatty coconut bay oil or soap. Dodecanoic acid is the main fatty acid in coconut oil (49%) and in palm kernel oil (47-50%), and is found in lesser amounts in wild nutmeg, human breast milk, cow‚Äôs milk, goat milk, watermelon seeds, plum and macadamia nut ( doi:10.1351/pac200173040685). Dodecanoic acid is one of the saturated fatty acids found in the oil of cannabis seeds ( Ref:DOI ). Dodecanoic acid, although slightly irritating to mucous membranes, has an extremely low toxicity, is inexpensive, has antimicrobial properties and so is used in many soaps and shampoos. It is reacted with sodium hydroxide to generate sodium laurate, which is soap. Dodecanoic acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid either saturated or unsaturated" (PMID: 12716665 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Undecanecarboxylic acid	ChEBI
ABL	ChEBI
C12 Fatty acid	ChEBI
C12:0	ChEBI
CH3-[CH2]10-COOH	ChEBI
Coconut oil fatty acids	ChEBI
DAO	ChEBI
Dodecoic acid	ChEBI
Dodecylcarboxylate	ChEBI
Dodecylic acid	ChEBI
Duodecyclic acid	ChEBI
Duodecylic acid	ChEBI
Lauric acid	ChEBI
Laurinsaeure	ChEBI
Laurostearic acid	ChEBI
N-Dodecanoic acid	ChEBI
Undecane-1-carboxylic acid	ChEBI
Vulvic acid	ChEBI
Dodecanoate	Kegg
1-Undecanecarboxylate	Generator
Dodecoate	Generator
Dodecylcarboxylic acid	Generator
Dodecylate	Generator
Duodecyclate	Generator
Duodecylate	Generator
Laate	Generator
Laic acid	Generator
Laurostearate	Generator
N-Dodecanoate	Generator
Undecane-1-carboxylate	Generator
Vulvate	Generator
Aliphat no. 4	HMDB
Edenor C 1298-100	HMDB
Emery 651	HMDB
Hystrene 9512	HMDB
Kortacid 1299	HMDB
Laurate	HMDB
Lunac L 70	HMDB
Lunac L 98	HMDB
Neo-fat 12	HMDB
Neo-fat 12-43	HMDB
Nissan naa 122	HMDB
Philacid 1200	HMDB
Prifac 2920	HMDB
Univol u 314	HMDB
1-Dodecanoic acid	HMDB
FA(12:0)	HMDB
Dodecanoic acid	PhytoBank

Chemical Formula

C₁₂H₂₄O₂

Average Molecular Weight

200.32

Monoisotopic Molecular Weight

200.1776

IUPAC Name

dodecanoic acid

Traditional Name

lauric acid

CAS Registry Number

143-07-7

SMILES

CCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

InChI Key

POULHZVOKOAJMA-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:30805 )
straight-chain saturated fatty acid (CHEBI:30805 )
Straight chain fatty acids (C02679 )
Saturated fatty acids (C02679 )
Straight chain fatty acids (LMFA01010012 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Industrial application:

Household products:

Antimicrobial agent:

Antibacterial

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	44 - 46 °C	Not Available
Boiling Point	282.5 °C at 512 mmHg	Wikipedia
Water Solubility	0.0048 mg/mL	Not Available
logP	4.60	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	5.13	ALOGPS
logP	4.48	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.95	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	10	ChemAxon
Refractivity	58.68 m³·mol⁻¹	ChemAxon
Polarizability	25.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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)	splash10-074l-9100000000-911a01d38925d0de481f	2014-09-20	View Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-a12b321a54a44ae28972	Spectrum
GC-MS	Dodecanoic acid, 1 TMS, GC-MS Spectrum	splash10-014i-2910000000-d52410168e784872a5a6	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-06xx-9100000000-1ef5cd411f38c53a0a92	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0706-9100000000-e66a9147257053b93702	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0706-9100000000-2dd666a9a0355b1ca144	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-074i-9300000000-405ec308fe8c935c62a2	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-067i-0930000000-6a80d41e346f4b10104c	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-a12b321a54a44ae28972	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-2910000000-d52410168e784872a5a6	Spectrum
GC-MS	Dodecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1910000000-8246864bf316bce609a2	Spectrum
Predicted GC-MS	Dodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9500000000-e05832f94ff0361363a2	Spectrum
Predicted GC-MS	Dodecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05g0-9310000000-038e232cccb44582ec9c	Spectrum
Predicted GC-MS	Dodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dodecanoic 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)	splash10-0udi-2290000000-861c4b7b2da35b82ef7f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4l-9100000000-966cf4c6621fcec41368	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-054o-9000000000-d43dd32656ad22e95fdd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-06xx-9100000000-a71409efaf5fdd6ab0e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive	splash10-0706-9100000000-eb09296a8c4c7c381b38	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-f22d8298d64e6f382279	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-0c79a7257b53685108c6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9600000000-25d268515337ef276c60	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-009b-9000000000-c00963f9b91f4a82e1ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-f22d8298d64e6f382279	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-0c79a7257b53685108c6	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, 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

Name	SMPDB/Pathwhiz	KEGG
Beta Oxidation of Very Long Chain Fatty Acids
Fatty Acid Biosynthesis		Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids		Not Available
Adrenoleukodystrophy, X-linked		Not Available
Carnitine-acylcarnitine translocase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phospholipase A2, membrane associated	PLA2G2A	1p35	P14555	details
Group IID secretory phospholipase A2	PLA2G2D	1p36.12	Q9UNK4	details
Peroxisomal carnitine O-octanoyltransferase	CROT	7q21.1	Q9UKG9	details
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	1p32	P23786	details
Alcohol dehydrogenase class-3	ADH5	4q23	P11766	details
Ganglioside GM2 activator	GM2A	5q33.1	P17900	details
Toll-like receptor 4	TLR4	9q33.1	O00206	details
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	3p21.31	O43772	details
S-acyl fatty acid synthase thioesterase, medium chain	OLAH	10p13	Q9NV23	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	3p21.31	O43772	details
Glycolipid transfer protein	GLTP	12q24.11	Q9NZD2	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phospholipase A2, membrane associated	PLA2G2A	1p35	P14555	details
Group IID secretory phospholipase A2	PLA2G2D	1p36.12	Q9UNK4	details
Alcohol dehydrogenase class-3	ADH5	4q23	P11766	details
Lactotransferrin	LTF	3p21.31	P02788	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Toll-like receptor 4	TLR4	9q33.1	O00206	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000638

DrugBank ID

DB03017

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30805

References

General References

Mensink RP, Zock PL, Kester AD, Katan MB: Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials. Am J Clin Nutr. 2003 May;77(5):1146-55. doi: 10.1093/ajcn/77.5.1146. [PubMed:12716665 ]

Only showing the first 10 proteins. There are 16 proteins in total.

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Enzymes

Enzyme Details

1. Phospholipase A2, membrane associated

General function:: Involved in phospholipase A2 activity
Specific function:: Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G2A
Uniprot ID:: P14555
Molecular weight:: 16082.525

Enzyme Details

2. Group IID secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:: PLA2G2D
Uniprot ID:: Q9UNK4
Molecular weight:: 16546.1

Enzyme Details

3. Peroxisomal carnitine O-octanoyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:: CROT
Uniprot ID:: Q9UKG9
Molecular weight:: 10213.63

Enzyme Details

4. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: P23786
Molecular weight:: 73776.335

Enzyme Details

5. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Enzyme Details

6. Ganglioside GM2 activator

General function:: Involved in sphingolipid activator protein activity
Specific function:: Binds gangliosides and stimulates ganglioside GM2 degradation. It stimulates only the breakdown of ganglioside GM2 and glycolipid GA2 by beta-hexosaminidase A. It extracts single GM2 molecules from membranes and presents them in soluble form to beta-hexosaminidase A for cleavage of N-acetyl-D-galactosamine and conversion to GM3
Gene Name:: GM2A
Uniprot ID:: P17900
Molecular weight:: 20838.1

Enzyme Details

7. Toll-like receptor 4

General function:: Involved in protein binding
Specific function:: Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response
Gene Name:: TLR4
Uniprot ID:: O00206
Molecular weight:: 95679.2

Enzyme Details

8. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Enzyme Details

9. S-acyl fatty acid synthase thioesterase, medium chain

General function:: Involved in biosynthetic process
Specific function:: In fatty acid biosynthesis chain termination and release of the free fatty acid product is achieved by hydrolysis of the thio ester by a thioesterase I, a component of the fatty acid synthetase complex. The chain length of the released fatty acid is usually C16. However, in the mammary glands of non-ruminant mammals, and in the uropygial gland of certain waterfowl there exists a second thioesterase which releases medium-chain length fatty acids (C8 to C2) (By similarity).
Gene Name:: OLAH
Uniprot ID:: Q9NV23
Molecular weight:: 29930.82

Transporters

Enzyme Details

1. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Enzyme Details

2. Glycolipid transfer protein

General function:: Involved in glycolipid transporter activity
Specific function:: Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides
Gene Name:: GLTP
Uniprot ID:: Q9NZD2
Molecular weight:: 23849.6

Only showing the first 10 proteins. There are 16 proteins in total.

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Showing Compound Card for Dodecanoic acid (CDB004852)

Structure for CDB004852 (Dodecanoic acid)

Enzymes

Transporters