Cannabis Compound Database: Showing Compound Card for cis-Vaccenoyl-CoA (CDB005305)

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Record Information

Version

1.0

Created at

2020-04-17 19:29:51 UTC

Updated at

2020-12-07 19:11:55 UTC

CannabisDB ID

CDB005305

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

cis-Vaccenoyl-CoA

Description

cis-Vaccenoyl CoA, also known as vaccenoyl coenzyme A or 11-octadecenoyl CoA, 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. cis-Vaccenoyl CoA is a strong basic compound (based on its pKa). cis-Vaccenoyl-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
11-Octadecenoyl CoA	HMDB
11-Octadecenoyl coenzyme A	HMDB
cis-Vaccenoyl coenzyme A	HMDB
cis-Vaccenoyl-CoA	HMDB
cis-Vaccenoyl-coenzyme	HMDB
cis-Vaccenoyl-coenzyme A	HMDB
R-11-Octadecenoate	HMDB
R-11-Octadecenoate CoA	HMDB
R-11-Octadecenoate coenzyme A	HMDB
R-11-Octadecenoic acid	HMDB
R-11-Octadecenoyl CoA	HMDB
R-11-Octadecenoyl coenzyme A	HMDB
Vaccenoyl CoA	HMDB
Vaccenoyl coenzyme A	HMDB
Vaccenoyl-CoA	HMDB
Vaccenoyl-coenzyme	HMDB
Vaccenoyl-coenzyme A	HMDB
Vaccenyl coenzyme A	HMDB

Chemical Formula

C₃₉H₆₈N₇O₁₇P₃S

Average Molecular Weight

1031.98

Monoisotopic Molecular Weight

1031.3605

IUPAC Name

{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(11E)-octadec-11-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy((3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(11E)-octadec-11-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

13673-88-6

SMILES

[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCC\C=C\CCCCCC)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h9-10,26-28,32-34,38,49-50H,4-8,11-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b10-9+/t28-,32?,33+,34+,38-/m1/s1

InChI Key

HEJOXXLSCAQQGQ-HHFSZNSTSA-N

Chemical Taxonomy

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

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Role

Industrial application:

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	2.83	ALOGPS
logP	1.13	ChemAxon
logS	-3.1	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	35	ChemAxon
Refractivity	246.97 m³·mol⁻¹	ChemAxon
Polarizability	102.64 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-3902020200-f86b94725c29a58610e0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1913140000-1d32cb163a97fc2fa14e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900010000-11cca0d7c51cc0c9c425	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-9761431500-77d50d2b249f1a52db7f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-4920210000-ec067874cf289e9db03f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-2725f27342a0d1efd2b4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-0afd0bffa1bd09c6b53c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-9010201300-a1772727e86615fcc7e2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9103401306-842fc3a3620a91f3e734	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-2e5dca73630e0cdc5de0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-5700100329-343447eb97db43076319	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0200790000-281446c2821ac1413e3c	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/14:0/18:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:0/18:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:0/14:0/18:1(11Z))		Not Available