Cannabis Compound Database: Showing Compound Card for Palmityl-CoA (CDB005302)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (59)transporters (2) Show 88 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:29:33 UTC

Updated at

2020-12-07 19:11:55 UTC

CannabisDB ID

CDB005302

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Palmityl-CoA

Description

hexadecanoyl-CoA belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Thus, hexadecanoyl-CoA is considered to be a fatty ester lipid molecule. hexadecanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, hexadecanoyl-CoA has been detected, but not quantified in, several different foods, such as hedge mustards, swedes, nances, pak choy, and sacred lotus. This could make hexadecanoyl-CoA a potential biomarker for the consumption of these foods. Palmityl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
coenzyme A, S-Hexadecanoate	ChEBI
Palmitoyl coenzyme A	ChEBI
S-Palmitoylcoenzyme A	ChEBI
coenzyme A, S-Hexadecanoic acid	Generator
Hexadecanoyl-CoA	ChEBI
CoA, Hexadecanoyl	MeSH
CoA, Palmityl	MeSH
Hexadecanoyl CoA	MeSH
coenzyme A, Palmitoyl	MeSH
Palmityl CoA	MeSH
CoA, Palmitoyl	MeSH
Palmitoyl CoA	MeSH
Hexadecanoyl-coenzyme A	HMDB
Palmityl coenzyme A	HMDB
Palmityl-CoA	HMDB
Palmityl-coenzyme A	HMDB
S-Palmityl coenzyme A	HMDB
S-Palmityl-CoA	HMDB
S-Palmityl-coenzyme A	HMDB

Chemical Formula

C₃₇H₆₆N₇O₁₇P₃S

Average Molecular Weight

1005.94

Monoisotopic Molecular Weight

1005.3449

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional Name

palmitoyl-coa

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1

InChI Key

MNBKLUUYKPBKDU-BBECNAHFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-fucopyranose (CHEBI:42589 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Role

Biological role:

Physical Properties

State

Solid

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	2.35	ALOGPS
logP	0.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	236.65 m³·mol⁻¹	ChemAxon
Polarizability	102.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2709000101-7863d2df84c4c4e06bd2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1829200000-77fb81a8f15c5d2b616c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1914000000-016e1dd6b88c119f09b8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0far-8971333504-cdf5697f5a74af8e63d1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-2910301001-24e89da24748049880af	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7900100000-2cd78f62ff0a7c2cb5b8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-9000000000-a5e30ac28e6aa4c5b77d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ug0-9010201301-1162e12d8cb42839e762	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004r-4102301209-063dede4760b705c02d9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-d041dea4fa9f52102bd4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3801000429-6b8dc383575e6c3d2b72	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0001900000-a96e69193e5f6d651546	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Long-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADL	2q34	P28330	details
Medium-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADM	1p31	P11310	details
Peroxisomal acyl-coenzyme A oxidase 1	ACOX1	17q25.1	Q15067	details
Peroxisomal acyl-coenzyme A oxidase 3	ACOX3	4p15.3	O15254	details
Diacylglycerol O-acyltransferase 1	DGAT1	8q24.3	O75907	details
Carnitine O-palmitoyltransferase 1, muscle isoform	CPT1B	22q13.33	Q92523	details
Carnitine O-palmitoyltransferase 1, liver isoform	CPT1A	11q13.2	P50416	details
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	1p32	P23786	details
Carnitine O-palmitoyltransferase 1, brain isoform	CPT1C	19q13.33	Q8TCG5	details
Bile acid-CoA:amino acid N-acyltransferase	BAAT	9q22.3	Q14032	details
Long-chain-fatty-acid--CoA ligase 4	ACSL4	Xq22.3-q23	O60488	details
Long-chain-fatty-acid--CoA ligase 1	ACSL1	4q35	P33121	details
Long-chain-fatty-acid--CoA ligase 6	ACSL6	5q31	Q9UKU0	details
Long-chain-fatty-acid--CoA ligase 5	ACSL5	10q25.1-q25.2	Q9ULC5	details
Long-chain-fatty-acid--CoA ligase 3	ACSL3	2q34-q35	O95573	details
Serine palmitoyltransferase 1	SPTLC1	9q22.2	O15269	details
Serine palmitoyltransferase 2	SPTLC2	14q24.3	O15270	details
Trans-2-enoyl-CoA reductase, mitochondrial	MECR	1p35.3	Q9BV79	details
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	1p36	O00154	details
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	14q24.3	P49753	details
Acyl-coenzyme A thioesterase 4	ACOT4	14q24.3	Q8N9L9	details
Palmitoyl-protein thioesterase 1	PPT1	1p32	P50897	details
Lysosomal thioesterase PPT2	PPT2		Q9UMR5	details
Phosphatidylinositol-glycan biosynthesis class W protein	PIGW		Q7Z7B1	details
Fatty acyl-CoA reductase 1	FAR1	11p15.2	Q8WVX9	details
Fatty acyl-CoA reductase 2	FAR2	12p11.22	Q96K12	details
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Xq13.1	Q6E213	details
Very long-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADVL	17p13.1	P49748	details
Serine palmitoyltransferase 3	SPTLC3	20p12.1	Q9NUV7	details
Acyl-coenzyme A thioesterase 1	ACOT1	14q24.3	Q86TX2	details
Cytosolic acyl coenzyme A thioester hydrolase-like	ACOT7L		Q6ZUV0	details
Long-chain-fatty-acid--CoA ligase ACSBG2	ACSBG2	19p13.3	Q5FVE4	details
Long-chain-fatty-acid--CoA ligase ACSBG1	ACSBG1	15q23-q24	Q96GR2	details
Acyl-coenzyme A thioesterase THEM5	THEM5	1q21.3	Q8N1Q8	details
Acyl-coenzyme A thioesterase THEM4	THEM4	1q21	Q5T1C6	details
Probable palmitoyltransferase ZDHHC11	ZDHHC11	5p15.33	Q9H8X9	details
Probable palmitoyltransferase ZDHHC12	ZDHHC12	9q34.11	Q96GR4	details
Palmitoyltransferase ZDHHC13	ZDHHC13	11p15.1	Q8IUH4	details
Probable palmitoyltransferase ZDHHC14	ZDHHC14	6q25.3	Q8IZN3	details
Palmitoyltransferase ZDHHC15	ZDHHC15	Xq13.3	Q96MV8	details
Probable palmitoyltransferase ZDHHC16	ZDHHC16	10q24.1	Q969W1	details
Palmitoyltransferase ZDHHC17	ZDHHC17	12q21.2	Q8IUH5	details
Palmitoyltransferase ZDHHC18	ZDHHC18	1p36.11	Q9NUE0	details
Probable palmitoyltransferase ZDHHC19	ZDHHC19	3q29	Q8WVZ1	details
Probable palmitoyltransferase ZDHHC20	ZDHHC20	13q12.11	Q5W0Z9	details
Palmitoyltransferase ZDHHC21	ZDHHC21	9p22.3	Q8IVQ6	details
Putative palmitoyltransferase ZDHHC22	ZDHHC22	14q24.3	Q8N966	details
Probable palmitoyltransferase ZDHHC23	ZDHHC23	3q13.31	Q8IYP9	details
Probable palmitoyltransferase ZDHHC24	ZDHHC24	11q13.2	Q6UX98	details
Probable palmitoyltransferase ZDHHC1	ZDHHC1	16q22.1	Q8WTX9	details
Palmitoyltransferase ZDHHC2	ZDHHC2	8p22	Q9UIJ5	details
Palmitoyltransferase ZDHHC3	ZDHHC3	3p21.31	Q9NYG2	details
Probable palmitoyltransferase ZDHHC4	ZDHHC4	7p22.1	Q9NPG8	details
Palmitoyltransferase ZDHHC5	ZDHHC5	11q12.1	Q9C0B5	details
Palmitoyltransferase ZDHHC6	ZDHHC6	10q25.2	Q9H6R6	details
Palmitoyltransferase ZDHHC7	ZDHHC7	16q24.1	Q9NXF8	details
Probable palmitoyltransferase ZDHHC8	ZDHHC8	22q11.21	Q9ULC8	details
Palmitoyltransferase ZDHHC9	ZDHHC9	Xq26.1	Q9Y397	details
Probable palmitoyltransferase ZDHHC11B	ZDHHC11B		P0C7U3	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Palmitoyltransferase ZDHHC13	ZDHHC13	11p15.1	Q8IUH4	details
Palmitoyltransferase ZDHHC17	ZDHHC17	12q21.2	Q8IUH5	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Trans-2-enoyl-CoA reductase, mitochondrial	MECR	1p35.3	Q9BV79	details
Probable palmitoyltransferase ZDHHC11	ZDHHC11	5p15.33	Q9H8X9	details
Probable palmitoyltransferase ZDHHC12	ZDHHC12	9q34.11	Q96GR4	details
Palmitoyltransferase ZDHHC13	ZDHHC13	11p15.1	Q8IUH4	details
Probable palmitoyltransferase ZDHHC14	ZDHHC14	6q25.3	Q8IZN3	details
Palmitoyltransferase ZDHHC15	ZDHHC15	Xq13.3	Q96MV8	details
Probable palmitoyltransferase ZDHHC16	ZDHHC16	10q24.1	Q969W1	details
Palmitoyltransferase ZDHHC17	ZDHHC17	12q21.2	Q8IUH5	details
Palmitoyltransferase ZDHHC18	ZDHHC18	1p36.11	Q9NUE0	details
Probable palmitoyltransferase ZDHHC19	ZDHHC19	3q29	Q8WVZ1	details
Probable palmitoyltransferase ZDHHC20	ZDHHC20	13q12.11	Q5W0Z9	details
Palmitoyltransferase ZDHHC21	ZDHHC21	9p22.3	Q8IVQ6	details
Putative palmitoyltransferase ZDHHC22	ZDHHC22	14q24.3	Q8N966	details
Probable palmitoyltransferase ZDHHC23	ZDHHC23	3q13.31	Q8IYP9	details
Probable palmitoyltransferase ZDHHC24	ZDHHC24	11q13.2	Q6UX98	details
Probable palmitoyltransferase ZDHHC1	ZDHHC1	16q22.1	Q8WTX9	details
Palmitoyltransferase ZDHHC2	ZDHHC2	8p22	Q9UIJ5	details
Palmitoyltransferase ZDHHC3	ZDHHC3	3p21.31	Q9NYG2	details
Probable palmitoyltransferase ZDHHC4	ZDHHC4	7p22.1	Q9NPG8	details
Palmitoyltransferase ZDHHC5	ZDHHC5	11q12.1	Q9C0B5	details
Palmitoyltransferase ZDHHC6	ZDHHC6	10q25.2	Q9H6R6	details
Palmitoyltransferase ZDHHC7	ZDHHC7	16q24.1	Q9NXF8	details
Probable palmitoyltransferase ZDHHC8	ZDHHC8	22q11.21	Q9ULC8	details
Palmitoyltransferase ZDHHC9	ZDHHC9	Xq26.1	Q9Y397	details
Probable palmitoyltransferase ZDHHC11B	ZDHHC11B		P0C7U3	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Palmitoyl-protein thioesterase 1	PPT1	1p32	P50897	details
Acyl-coenzyme A thioesterase THEM4	THEM4	1q21	Q5T1C6	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001338

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

Not Available

METLIN ID

Not Available

PubChem Compound

644109

PDB ID

Not Available

ChEBI ID

15525

References

General References

Not Available

Only showing the first 10 proteins. There are 88 proteins in total.

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Enzymes

Enzyme Details

1. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Enzyme Details

2. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Enzyme Details

3. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

Enzyme Details

4. Peroxisomal acyl-coenzyme A oxidase 3

General function:: Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:: Oxidizes the CoA-esters of 2-methyl-branched fatty acids (By similarity).
Gene Name:: ACOX3
Uniprot ID:: O15254
Molecular weight:: 69574.075

Enzyme Details

5. Diacylglycerol O-acyltransferase 1

General function:: Involved in diacylglycerol O-acyltransferase activity
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
Gene Name:: DGAT1
Uniprot ID:: O75907
Molecular weight:: 55277.735

Enzyme Details

6. Carnitine O-palmitoyltransferase 1, muscle isoform

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT1B
Uniprot ID:: Q92523
Molecular weight:: 83890.705

Enzyme Details

7. Carnitine O-palmitoyltransferase 1, liver isoform

General function:: Involved in acyltransferase activity
Specific function:: Catalyzes the transfer of the acyl group of long-chain fatty acid-CoA conjugates onto carnitine, an essential step for the mitochondrial uptake of long-chain fatty acids and their subsequent beta-oxidation in the mitochondrion. Plays an important role in triglyceride metabolism.
Gene Name:: CPT1A
Uniprot ID:: P50416
Molecular weight:: 86238.415

Enzyme Details

8. 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

9. Carnitine O-palmitoyltransferase 1, brain isoform

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT1C
Uniprot ID:: Q8TCG5
Molecular weight:: 89712.575

Enzyme Details

10. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Transporters

Enzyme Details

1. Palmitoyltransferase ZDHHC13

General function:: Not Available
Specific function:: Palmitoyltransferase for HD and GAD2 (By similarity). Mediates Mg(2+) transport (By similarity).
Gene Name:: ZDHHC13
Uniprot ID:: Q8IUH4
Molecular weight:: 56508.075

Enzyme Details

2. Palmitoyltransferase ZDHHC17

General function:: Not Available
Specific function:: Palmitoyltransferase specific for a subset of neuronal proteins, including SNAP25, DLG4/PSD95, GAD2, SYT1 and HD. Palmitoylates MPP1 in erythrocytes. May be involved in the sorting or targeting of critical proteins involved in the initiating events of endocytosis at the plasma membrane. Has transforming activity. Mediates Mg(2+) transport.
Gene Name:: ZDHHC17
Uniprot ID:: Q8IUH5
Molecular weight:: 72639.345

Only showing the first 10 proteins. There are 88 proteins in total.

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Showing Compound Card for Palmityl-CoA (CDB005302)

Structure for CDB005302 (Palmityl-CoA)

Enzymes

Transporters