Cannabis Compound Database: Showing Compound Card for Squalene (CDB005225)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4)transporters (2) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:21:53 UTC

Updated at

2021-01-04 18:49:00 UTC

CannabisDB ID

CDB005225

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Squalene

Description

Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds. It belongs to the class of compounds known as triterpenoids. These are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Triterpenes are biosynthesized through the head-to-head condensation of two FPP units to form squalene. In turn, squalene serves as precursor for the formation of triterpenoids, including bacterial hopanoids and eukaryotic sterols. Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks). Squalene is a low-density compound that is stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the shark's liver, is lighter than water with a specific gravity of 0.855 (Wikipedia ). Squalene can also be isolated through botanical sources as well, including rice bran, wheat germ, and olives. It occurs in high concentrations in the stomach oil of birds in the order Procellariiformes.Industrially, squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials. All higher organisms produce squalene, including yeast, plants, insects, fish and humans. However, blue-green algae and some bacteria do not manufacture squalene and must acquire it from the environment if they need it. Squalene may function as a pheromone and is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) It is also found in human sebum (5%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a biochemical precursor to nearly all steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is also a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(all-e)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene	ChEBI
Spinacene	ChEBI
Supraene	ChEBI
(e,e,e,e)-Squalene	HMDB
all-trans-Squalene	HMDB
trans-Squalene	HMDB
Squalene	HMDB

Chemical Formula

C₃₀H₅₀

Average Molecular Weight

410.73

Monoisotopic Molecular Weight

410.3913

IUPAC Name

(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Traditional Name

squalene

CAS Registry Number

111-02-4

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C

InChI Identifier

InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+

InChI Key

YYGNTYWPHWGJRM-AAJYLUCBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Branched unsaturated hydrocarbon
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

triterpene (CHEBI:15440 )
Acyclic triterpenoids (C00751 )
Liner triterpenes (C00751 )
Acyclic triterpenoids (LMPR0106010002 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Biological location:

Tissue and substructures:

Epidermis

Cell and elements:

Extracellular

Cell:

Fibroblast

Organ and components:

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Biological role:

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-75 °C	Not Available
Boiling Point	285 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	12.188	Wikipedia

Predicted Properties

Property	Value	Source
logP	8.64	ALOGPS
logP	10.42	ChemAxon
logS	-5.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	144.62 m³·mol⁻¹	ChemAxon
Polarizability	56.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0159-9610000000-aaf0145da95343082ae1	2015-03-01	View Spectrum
GC-MS	Squalene, non-derivatized, GC-MS Spectrum	splash10-001i-9600000000-280b7ccaed0215f0937c	Spectrum
GC-MS	Squalene, non-derivatized, GC-MS Spectrum	splash10-015i-9500000000-63fc959bf17e2f6e0381	Spectrum
Predicted GC-MS	Squalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05dv-4879000000-3cfdaa630f73c021be06	Spectrum
Predicted GC-MS	Squalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-047r-1944600000-5faa7a5eb4804dfad261	2019-11-13	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-4867900000-dcd3ba4f6ee550dc565b	2019-11-13	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-2944400000-8be7743f6b07ba138c24	2019-11-13	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-2920300000-04f33a28f9d38283345e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0323900000-9162860711ec9f8266fe	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02fx-2984100000-742302f14e45ce03bfdd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-6495000000-83c6df474790679c40e3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-4905353fab78414bcab2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-e7195906634d18bf31dd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1869100000-2d7d4eb74fe0c5856cbf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2844900000-f00046ef895fbe9888a3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mk-4928000000-3dfbc6d8fc1271828c3b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5j-4932000000-6f14fcc4a6e8029a1652	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-45d1d2cb6b79e3bc92ae	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0102900000-49aa25403f6062cc3520	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002o-1239000000-809fbf3fc0f0117fe5d1	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Squalene monooxygenase	SQLE	8q24.1	Q14534	details
Squalene synthase	FDFT1	8p23.1-p22	P37268	details
Serine palmitoyltransferase 1	SPTLC1	9q22.2	O15269	details
Putative uncharacterized protein DKFZp686B0215	DKFZp686B0215		Q5HYI4	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
SEC14-like protein 3	SEC14L3	22q12.2	Q9UDX4	details
SEC14-like protein 4	SEC14L4	22q12.2	Q9UDX3	details

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000256

DrugBank ID

DB11460

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Squalene

METLIN ID

Not Available

PubChem Compound

638072

PDB ID

Not Available

ChEBI ID

15440

References

General References

Not Available

Enzymes

Enzyme Details

1. Squalene monooxygenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name:: SQLE
Uniprot ID:: Q14534
Molecular weight:: 63922.505

Enzyme Details

2. Squalene synthase

General function:: Involved in transferase activity
Specific function:: Not Available
Gene Name:: FDFT1
Uniprot ID:: P37268
Molecular weight:: 48114.87

Enzyme Details

3. Serine palmitoyltransferase 1

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Serine palmitoyltransferase (SPT). The heterodimer formed with SPTLC2 or SPTLC3 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC3-SPTSSA isozyme uses both C14-CoA and C16-CoA as substrates, with a slight preference for C14-CoA. The SPTLC1-SPTLC2-SPTSSB complex shows a strong preference for C18-CoA substrate, while the SPTLC1-SPTLC3-SPTSSB isozyme displays an ability to use a broader range of acyl-CoAs, without apparent preference.
Gene Name:: SPTLC1
Uniprot ID:: O15269
Molecular weight:: 52743.41

Enzyme Details

4. Putative uncharacterized protein DKFZp686B0215

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: DKFZp686B0215
Uniprot ID:: Q5HYI4
Molecular weight:: 63793.4

Transporters

Enzyme Details

1. SEC14-like protein 3

General function:: Involved in transporter activity
Specific function:: Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids
Gene Name:: SEC14L3
Uniprot ID:: Q9UDX4
Molecular weight:: 46047.8

Enzyme Details

2. SEC14-like protein 4

General function:: Involved in transporter activity
Specific function:: Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids
Gene Name:: SEC14L4
Uniprot ID:: Q9UDX3
Molecular weight:: 46643.4

Showing Compound Card for Squalene (CDB005225)

Structure for CDB005225 (Squalene)

Enzymes

Transporters