Showing metabocard for Squalene (BMDB0000256)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:29 UTC
Update Date2020-05-19 22:01:18 UTC
BMDB IDBMDB0000256
Secondary Accession Numbers
  • BMDB00256
Metabolite Identification
Common NameSqualene
DescriptionSqualene, also known as spinacene or supraene, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, squalene is considered to be an isoprenoid lipid molecule. Squalene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(all-e)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaeneChEBI
SpinaceneChEBI
SupraeneChEBI
(e,e,e,e)-SqualeneHMDB
all-trans-SqualeneHMDB
trans-SqualeneHMDB
SqualeneHMDB
Chemical FormulaC30H50
Average Molecular Weight410.73
Monoisotopic Molecular Weight410.39125161
IUPAC Name(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
Traditional Namesqualene
CAS Registry Number111-02-4
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 KeyYYGNTYWPHWGJRM-AAJYLUCBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-75 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.64ALOGPS
logP10.42ChemAxon
logS-5.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity144.62 m³·mol⁻¹ChemAxon
Polarizability56.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9600000000-280b7ccaed0215f0937cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015i-9500000000-63fc959bf17e2f6e0381View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dv-4879000000-3cfdaa630f73c021be06View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-047r-1944600000-5faa7a5eb4804dfad261View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-4867900000-dcd3ba4f6ee550dc565bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2944400000-8be7743f6b07ba138c24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2920300000-04f33a28f9d38283345eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0323900000-9162860711ec9f8266feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02fx-2984100000-742302f14e45ce03bfddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-6495000000-83c6df474790679c40e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-4905353fab78414bcab2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-e7195906634d18bf31ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1869100000-2d7d4eb74fe0c5856cbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2844900000-f00046ef895fbe9888a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-4928000000-3dfbc6d8fc1271828c3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5j-4932000000-6f14fcc4a6e8029a1652View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-45d1d2cb6b79e3bc92aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0102900000-49aa25403f6062cc3520View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-1239000000-809fbf3fc0f0117fe5d1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0159-9610000000-aaf0145da95343082ae1View in MoNA
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Epidermis
  • Fibroblasts
  • Liver
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000256
DrugBank IDDB11460
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00003755
Chemspider ID553635
KEGG Compound IDC00751
BioCyc IDSQUALENE
BiGG IDNot Available
Wikipedia LinkSqualene
METLIN IDNot Available
PubChem Compound638072
PDB IDNot Available
ChEBI ID15440
References
Synthesis ReferencePeng, Wanxi; Li, Kaifu. Method of preparation of squalene. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Squalene synthase
General function:
Lipid transport and metabolism
Specific function:
Critical branch point enzyme of isoprenoid biosynthesis that is thought to regulate the flux of isoprene intermediates through the sterol pathway.
Gene Name:
FDFT1
Uniprot ID:
Q32KR6
Molecular weight:
48304.0
Reactions
2 Farnesyl pyrophosphate + NADPH → Squalene + NADP +2 Pyrophosphatedetails