Showing Compound Heptadecanoyl-CoA (FDB023941)

Record Information

Version

1.0

Creation date

2011-09-21 00:37:08 UTC

Update date

2015-07-21 06:57:57 UTC

Primary ID

FDB023941

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Heptadecanoyl-CoA

Description

Heptadecanoyl CoA is an intermediate in lipid metabolism. The protein carnitine palmitoyltransferase II (mitochondrial) irreversibly transports heptadecanoate into the mitochondria. In the mitochondria, the enzyme acyl-CoA dehydrogenase [EC:1.3.99.3] catalyzes the irreversible catabolism of this metabolite to acetyl-CoA and propanoyl-CoA. In the cytosol, the enzyme carnitine O-palmitoyltransferase [EC:2.3.1.21] catalyzes the irreversible conversion of this metabolite to heptadecanoyl carnitine and the enzyme long-chain-fatty-acid-CoA ligase [EC:6.2.1.3] reversibly catalyzes the production of this metabolite from heptadecanoate. (BiGG database) [HMDB]

CAS Number

3546-17-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Heptadecanoyl-coenzyme A	ChEBI
Heptadecanoate	HMDB
Heptadecanoic acid	HMDB
Heptadecanoic acid CoA	HMDB
Heptadecanoyl coenzyme A	HMDB
Heptadecanoyl-CoA	HMDB
Heptadecyl-CoA	HMDB
Heptadecyl-coenzyme A	HMDB
Margaric acid CoA	HMDB
Margaroyl coenzyme A	HMDB
N-Heptadecanoate	HMDB
N-Heptadecanoic acid	HMDB
N-Heptadecanoic acid coenzyme A	HMDB
S-Heptadecanoate	HMDB
S-Heptadecanoate coenzyme A	HMDB
S-Heptadecanoate-coenzyme A	HMDB
S-Heptadecanoic acid	HMDB
S-Heptadecanoyl CoA	HMDB
S-Heptadecanoyl coenzyme A	HMDB
Heptadecanoic acid coa	hmdb
Heptadecanoyl-coA	hmdb
Heptadecanoyl-coenzyme a	hmdb
Heptadecyl-coA	hmdb
Heptadecyl-coenzyme a	hmdb
Margaric acid coa	hmdb
n-Heptadecanoic acid coenzyme a	hmdb
s-heptadecanoate	hmdb
S-heptadecanoate coenzyme A	hmdb
s-heptadecanoate-coenzyme a	hmdb
s-heptadecanoic acid	hmdb
s-Heptadecanoyl coenzyme A	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	1.23 g/L	ALOGPS
logP	2.61	ALOGPS
logP	-0.051	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	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	35	ChemAxon
Refractivity	241.25 m³·mol⁻¹	ChemAxon
Polarizability	102.54 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

Chemical Formula

C38H68N7O17P3S

IUPAC name

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

InChI Identifier

InChI=1S/C38H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-29(47)66-22-21-40-28(46)19-20-41-36(50)33(49)38(2,3)24-59-65(56,57)62-64(54,55)58-23-27-32(61-63(51,52)53)31(48)37(60-27)45-26-44-30-34(39)42-25-43-35(30)45/h25-27,31-33,37,48-49H,4-24H2,1-3H3,(H,40,46)(H,41,50)(H,54,55)(H,56,57)(H2,39,42,43)(H2,51,52,53)/t27-,31-,32-,33+,37-/m1/s1

InChI Key

DRABUZIHHACUPI-DUPKZGIXSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCCC(=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=C(N)N=CN=C12

Average Molecular Weight

1019.97

Monoisotopic Molecular Weight

1019.360524011

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

long-chain fatty acyl-CoA (CHEBI:74397 )
11,12-saturated fatty acyl-CoA (CHEBI:74397 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Biochemical process:

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

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-4902110200-db5443e07e150b0ec7d1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1913130000-a3c3e7ad6d370a0d9ab8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900010000-be853ba709390a162e5f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0lgi-9761332400-df46f923c788e4633547	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4921201000-103592f0573f96ddf6a4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900000000-f863779e788bb009e57b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-b60e8c6845a544b99284	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016r-9010201300-38edd61504f16ec953af	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004r-8103401309-d69730a7d790b0b5c65a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-94bf02cb6c8de72ec588	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-7000200629-c0856e9611760f88f172	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0100590000-4ba435930803a1cdd95a	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2339497

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

3082004

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06497

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

2415330

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Glycine N-acyltransferase	GLYAT	Q6IB77
Glycine N-acyltransferase-like protein 1	GLYATL1	Q969I3
Glycine N-acyltransferase-like protein 2	GLYATL2	Q8WU03
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Liver carboxylesterase 1	CES1	P23141
Pancreatic triacylglycerol lipase	PNLIP	P16233
Hepatic triacylglycerol lipase	LIPC	P11150
Inactive pancreatic lipase-related protein 1	PNLIPRP1	P54315
Patatin-like phospholipase domain-containing protein 3	PNPLA3	Q9NST1
Gastric triacylglycerol lipase	LIPF	P07098
Endothelial lipase	LIPG	Q9Y5X9
Diacylglycerol O-acyltransferase 1	DGAT1	O75907
Pancreatic lipase-related protein 2	PNLIPRP2	P54317
Lipoprotein lipase	LPL	P06858
2-acylglycerol O-acyltransferase 2	MOGAT2	Q3SYC2
Patatin-like phospholipase domain-containing protein 4	PNPLA4	P41247
Diacylglycerol O-acyltransferase 2	DGAT2	Q96PD7
2-acylglycerol O-acyltransferase 1	MOGAT1	Q96PD6
2-acylglycerol O-acyltransferase 3	MOGAT3	Q86VF5
Glycerol-3-phosphate acyltransferase 3	AGPAT9	Q53EU6
Patatin-like phospholipase domain-containing protein 2	PNPLA2	Q96AD5
Pancreatic lipase-related protein 3	PNLIPRP3	Q17RR3
Cholinesterase	BCHE	P06276
Fatty acyl-CoA reductase 2	FAR2	Q96K12
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Q6E213
Carboxylesterase 5A	CES5A	Q6NT32
60 kDa lysophospholipase	ASPG	Q86U10
Fatty acid synthase	FASN	P49327
Sterol O-acyltransferase 1	SOAT1	P35610
Galactoside-binding soluble lectin 13	LGALS13	Q9UHV8
Eosinophil lysophospholipase	CLC	Q05315
Cocaine esterase	CES2	O00748
Acylphosphatase-2	ACYP2	P14621
Acylphosphatase-1	ACYP1	P07311
Aspartoacylase	ASPA	P45381
Aspartoacylase-2	ACY3	Q96HD9
Acid ceramidase	ASAH1	Q13510
Homeodomain-interacting protein kinase 1	HIPK1	Q86Z02
Peroxisome proliferator-activated receptor gamma	PPARG	P37231
Long-chain fatty acid transport protein 6	SLC27A6	Q9Y2P4
Long-chain fatty acid transport protein 3	SLC27A3	Q5K4L6
Long-chain fatty acid transport protein 4	SLC27A4	Q6P1M0
Putative neutral ceramidase C	ASAH2C	P0C7U2
Alkaline ceramidase 2	ACER2	Q5QJU3
Neutral ceramidase	ASAH2	Q9NR71
Alkaline ceramidase 1	ACER1	Q8TDN7
Neuropathy target esterase	PNPLA6	Q8IY17
Carboxylesterase 3	CES3	Q6UWW8
Fatty acyl-CoA reductase 1	FAR1	Q8WVX9
Acyl-CoA wax alcohol acyltransferase 1	AWAT1	Q58HT5
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2
Diacylglycerol O-acyltransferase 2-like protein 6	DGAT2L6	Q6ZPD8
Putative diacylglycerol O-acyltransferase 2-like protein 7	DGAT2L7	Q6IED9
Acyl-CoA-binding protein	DBI	P07108
Peroxisome proliferator-activated receptor delta	PPARD	Q03181
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	P21953
Cytosolic acyl coenzyme A thioester hydrolase-like	ACOT7L	Q6ZUV0
Long-chain-fatty-acid--CoA ligase ACSBG2	ACSBG2	Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1	ACSBG1	Q96GR2
3-ketoacyl-CoA thiolase, mitochondrial	ACAA2	P42765
Peroxisomal trans-2-enoyl-CoA reductase	PECR	Q9BY49
Bile acyl-CoA synthetase	SLC27A5	Q9Y2P5
Sterol O-acyltransferase 2	SOAT2	O75908
Acyl-CoA synthetase family member 4	AASDH	Q4L235
Glycerol-3-phosphate acyltransferase 1, mitochondrial	GPAM	Q9HCL2
Glycerol-3-phosphate acyltransferase 4	AGPAT6	Q86UL3
Glycerol-3-phosphate acyltransferase 2, mitochondrial	GPAT2	Q6NUI2
Very long-chain acyl-CoA synthetase	SLC27A2	O14975
Lysophospholipid acyltransferase 5	LPCAT3	Q6P1A2
1-acyl-sn-glycerol-3-phosphate acyltransferase gamma	AGPAT3	Q9NRZ7
1-acyl-sn-glycerol-3-phosphate acyltransferase beta	AGPAT2	O15120
1-acyl-sn-glycerol-3-phosphate acyltransferase alpha	AGPAT1	Q99943
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon	AGPAT5	Q9NUQ2
1-acyl-sn-glycerol-3-phosphate acyltransferase delta	AGPAT4	Q9NRZ5
Lysocardiolipin acyltransferase 1	LCLAT1	Q6UWP7
Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial	DBT	P11182
3-ketoacyl-CoA thiolase, peroxisomal	ACAA1	P09110
Trifunctional enzyme subunit beta, mitochondrial	HADHB	P55084
Dihydroxyacetone phosphate acyltransferase	GNPAT	O15228
Peroxisome proliferator-activated receptor alpha	PPARA	Q07869
Fatty acid-binding protein, heart	FABP3	P05413
Acyl-CoA dehydrogenase family member 10	ACAD10	Q6JQN1
Acyl-CoA dehydrogenase family member 11	ACAD11	Q709F0
Lysophospholipid acyltransferase LPCAT4	LPCAT4	Q643R3
Enoyl-CoA delta isomerase 2, mitochondrial	ECI2	O75521
Nef-associated protein 1	C9orf156	Q9BU70
Acyl-coenzyme A thioesterase 9, mitochondrial	ACOT9	Q9Y305
Acyl-CoA synthetase family member 3, mitochondrial	ACSF3	Q4G176
Acyl-CoA synthetase family member 2, mitochondrial	ACSF2	Q96CM8
Acyl-coenzyme A thioesterase 11	ACOT11	Q8WXI4