Cannabis Compound Database: Showing Compound Card for 9,10-Epoxyoctadecanoic acid (CDB005066)

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Record Information

Version

1.0

Created at

2020-04-17 19:05:56 UTC

Updated at

2020-12-07 19:11:30 UTC

CannabisDB ID

CDB005066

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

9,10-Epoxyoctadecanoic acid

Description

(9R,10S)-9,10-epoxy-18-hydroxyoctadecanoic acid, also known as (9R,10S)-18-hydroxy-9,10-epoxystearic acid or 18-hydroxy-(9R,10S)-epoxy-octadecanoic 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 (9R,10S)-9,10-epoxy-18-hydroxyoctadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 9,10-Epoxyoctadecanoic acid 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
(9R,10S)-18-Hydroxy-9,10-epoxystearic acid	ChEBI
18-Hydroxy-(9R,10S)-9,10-epoxystearic acid	ChEBI
18-Hydroxy-(9R,10S)-epoxy-octadecanoic acid	ChEBI
(9R,10S)-18-Hydroxy-9,10-epoxystearate	Generator
18-Hydroxy-(9R,10S)-9,10-epoxystearate	Generator
18-Hydroxy-(9R,10S)-epoxy-octadecanoate	Generator
9,10-Epoxyoctadecanoate	Generator
(9R,10S)-9,10-Epoxy-18-hydroxyoctadecanoate	HMDB
18-Hydroxy-9,10-epoxyoctadecanoic acid	HMDB
18-Hydroxy-9,10-epoxystearic acid	HMDB
3-(8-Hydroxyoctyl)-2-oxiraneoctanoic acid	HMDB
9,10-Epoxy-18-hydroxyoctadecanoic acid	HMDB
9,10-Epoxy-18-hydroxystearate	HMDB
9R,10S-Epoxy-18-hydroxystearate	HMDB
Omega-hydroxy-9,10-epoxystearic acid	HMDB
Ω-hydroxy-9,10-epoxystearic acid	HMDB
9,10-Epoxyoctadecanoic acid	HMDB

Chemical Formula

C₁₈H₃₄O₄

Average Molecular Weight

314.47

Monoisotopic Molecular Weight

314.2457

IUPAC Name

8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

Traditional Name

8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

CAS Registry Number

154966-80-0

SMILES

OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O4/c19-15-11-7-2-1-4-8-12-16-17(22-16)13-9-5-3-6-10-14-18(20)21/h16-17,19H,1-15H2,(H,20,21)/t16-,17+/m0/s1

InChI Key

ITTPZDMHCNGAGQ-DLBZAZTESA-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
Epoxy fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000003 )

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	5.33	ALOGPS
logP	4.41	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	87.74 m³·mol⁻¹	ChemAxon
Polarizability	39.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	9,10-Epoxyoctadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	9,10-Epoxyoctadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	9,10-Epoxyoctadecanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	9,10-Epoxyoctadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0029000000-c9984dbae9e0dc9dc39d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1169000000-47e7f6fa97d4b5b972c2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-6795000000-287ce7e76cbebaa25efd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-1191000000-0c89eebc496d9082fe21	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00os-8892000000-5898ae59b9d69139cfa7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aos-9400000000-c266cb2d66410ceb45b7	2021-09-23	View Spectrum