Cannabis Compound Database: Showing Compound Card for 3-Hydroxydocosanoyl-CoA (CDB005060)

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Record Information

Version

1.0

Created at

2020-04-17 19:05:17 UTC

Updated at

2020-12-07 19:11:30 UTC

CannabisDB ID

CDB005060

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

3-Hydroxydocosanoyl-CoA

Description

3-Hydroxydocosanoyl-CoA belongs to the class of organic compounds known as very-long-chain (3r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative, to which the acyl chain carries at least 22 carbon atoms. 3-Hydroxydocosanoyl-CoA is a strong basic compound (based on its pKa). 3-Hydroxydocosanoyl-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
(R)-3-Hydroxybehenoyl-coenzyme A	ChEBI
(R)-3-Hydroxydocosanoyl-CoA	ChEBI
(R)-3-Hydroxydocosanoyl-coenzyme A	ChEBI

Chemical Formula

C₄₃H₇₈N₇O₁₈P₃S

Average Molecular Weight

1106.1

Monoisotopic Molecular Weight

1105.4337

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3R)-3-hydroxydocosanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-{2-[(2-{[(3R)-3-hydroxydocosanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid

CAS Registry Number

1072942-17-6

SMILES

CCCCCCCCCCCCCCCCCCC[C@@H](O)CC(=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/C43H78N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-31(51)26-34(53)72-25-24-45-33(52)22-23-46-41(56)38(55)43(2,3)28-65-71(62,63)68-70(60,61)64-27-32-37(67-69(57,58)59)36(54)42(66-32)50-30-49-35-39(44)47-29-48-40(35)50/h29-32,36-38,42,51,54-55H,4-28H2,1-3H3,(H,45,52)(H,46,56)(H,60,61)(H,62,63)(H2,44,47,48)(H2,57,58,59)/t31-,32-,36-,37-,38+,42-/m1/s1

InChI Key

VNJQSRVXTRJVAZ-ZUIQSSPPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very-long-chain (3r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative, to which the acyl chain carries at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Very-long-chain (3R)-3-hydroxyacyl 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:76459 )
11,12-saturated fatty acyl-CoA (CHEBI:76459 )
3-hydroxy fatty acyl-CoA (CHEBI:76459 )
(R)-3-hydroxyacyl-CoA (CHEBI:76459 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Role

Biological role:

Physical Properties

State

Not Available

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	3.49	ALOGPS
logP	3.67	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	390.84 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	266.81 m³·mol⁻¹	ChemAxon
Polarizability	116.15 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-4901810200-36bd52efa1578cc40de1	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1902720000-fc4c5f69ea5b9f0d8ec4	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900400000-2bc10a015d075771ddd8	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-6914231500-10b543a221084497cdb0	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5901220100-16c446434bd8ac25f388	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-8bc2cc023f9fed0ab9dd	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-6900000000-67ac22f999ac835a8929	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-8900100151-2f74593f1c13a19d7330	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0000190000-9a21e4668b54b9e5ab79	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-9900aa2e1b7df9b23937	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ug0-7900201330-f4e433081686907345b2	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004u-9202401500-a15174a29a00bcc10c24	2021-10-12	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0060216

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30785935

KEGG Compound ID

Not Available

BioCyc ID

CPD-14276

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72193818

PDB ID

Not Available

ChEBI ID

76459

References

General References

Not Available

Showing Compound Card for 3-Hydroxydocosanoyl-CoA (CDB005060)

Structure for CDB005060 (3-Hydroxydocosanoyl-CoA)