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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:55:58 UTC
HMDB IDHMDB0000256
Secondary Accession Numbers
  • HMDB00256
Metabolite Identification
Common NameSqualene
DescriptionSqualene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds 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 volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawley's Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of 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 a low-density compound often 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 is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances).
Structure
Data?1582752119
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
SqualeneHMDB
all-trans-SqualeneHMDB
trans-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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
Water Solubility0.0005 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9600000000-280b7ccaed0215f0937cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015i-9500000000-63fc959bf17e2f6e0381Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dv-4879000000-3cfdaa630f73c021be06Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-047r-1944600000-5faa7a5eb4804dfad261Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-4867900000-dcd3ba4f6ee550dc565bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2944400000-8be7743f6b07ba138c24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0323900000-9162860711ec9f8266feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02fx-2984100000-742302f14e45ce03bfddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-6495000000-83c6df474790679c40e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-4905353fab78414bcab2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-e7195906634d18bf31ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1869100000-2d7d4eb74fe0c5856cbfSpectrum
MSMass Spectrum (Electron Ionization)splash10-0159-9610000000-aaf0145da95343082ae1Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
  • Sweat
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Liver
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.22 +/- 0.063 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.58 +/- 0.063 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SweatDetected but not Quantified Adult BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB11460
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00003755
Chemspider ID553635
KEGG Compound IDC00751
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSqualene
METLIN IDNot Available
PubChem Compound638072
PDB IDNot Available
ChEBI ID15440
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferencePeng, Wanxi; Li, Kaifu. Method of preparation of squalene. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Strauss JS, Stranieri AM, Farrell LN, Downing DT: The effect of marked inhibition of sebum production with 13cis-retinoic acid on skin surface lipid composition. J Invest Dermatol. 1980 Feb;74(2):66-7. [PubMed:6444323 ]
  2. Grimes DS, Hindle E, Dyer T: Sunlight, cholesterol and coronary heart disease. QJM. 1996 Aug;89(8):579-89. [PubMed:8935479 ]
  3. Relas H, Gylling H, Miettinen TA: Dietary squalene increases cholesterol synthesis measured with serum non-cholesterol sterols after a single oral dose in humans. Atherosclerosis. 2000 Oct;152(2):377-83. [PubMed:10998465 ]
  4. Nikkila K, Hockerstedt K, Miettinen TA: Serum and hepatic cholestanol, squalene and noncholesterol sterols in man: a study on liver transplantation. Hepatology. 1992 May;15(5):863-70. [PubMed:1568728 ]
  5. Gylling H, Relas H, Miettinen HE, Radhakrishnan R, Miettinen TA: Delayed postprandial retinyl palmitate and squalene removal in a patient heterozygous for apolipoprotein A-IFIN mutation (Leu 159-->Arg) and low HDL cholesterol level without coronary artery disease. Atherosclerosis. 1996 Dec 20;127(2):239-43. [PubMed:9125314 ]
  6. Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91. [PubMed:10758959 ]
  7. Rajaratnam RA, Gylling H, Miettinen TA: Serum squalene in postmenopausal women without and with coronary artery disease. Atherosclerosis. 1999 Sep;146(1):61-4. [PubMed:10487487 ]
  8. Thiele JJ, Weber SU, Packer L: Sebaceous gland secretion is a major physiologic route of vitamin E delivery to skin. J Invest Dermatol. 1999 Dec;113(6):1006-10. [PubMed:10594744 ]
  9. Relas H, Gylling H, Miettinen TA: Effect of stanol ester on postabsorptive squalene and retinyl palmitate. Metabolism. 2000 Apr;49(4):473-8. [PubMed:10778871 ]
  10. Gylling H, Vuoristo M, Farkkila M, Miettinen TA: The metabolism of cholestanol in primary biliary cirrhosis. J Hepatol. 1996 Apr;24(4):444-51. [PubMed:8738731 ]
  11. Chiba K, Yoshizawa K, Makino I, Kawakami K, Onoue M: Changes in the levels of glutathione after cellular and cutaneous damage induced by squalene monohydroperoxide. J Biochem Mol Toxicol. 2001;15(3):150-8. [PubMed:11424225 ]
  12. Nosaka Y, Yamanishi Y, Hirayama C: Biliary squalene levels in hepatobiliary disease. Gastroenterol Jpn. 1985 Aug;20(4):338-43. [PubMed:4054510 ]
  13. Kohno Y, Egawa Y, Itoh S, Nagaoka S, Takahashi M, Mukai K: Kinetic study of quenching reaction of singlet oxygen and scavenging reaction of free radical by squalene in n-butanol. Biochim Biophys Acta. 1995 Apr 28;1256(1):52-6. [PubMed:7742356 ]

Enzymes

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
Reactions
Squalene + NADPH + Oxygen → (3S)-2,3-epoxy-2,3-dihydrosqualene + NADP + Waterdetails
Squalene + Reduced acceptor + Oxygen → (S)-2,3-Epoxysqualene + Acceptor + Waterdetails
Squalene + Oxygen + NADPH + Hydrogen Ion → (S)-2,3-Epoxysqualene + NADP + Waterdetails
General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
FDFT1
Uniprot ID:
P37268
Molecular weight:
48114.87
Reactions
Farnesyl pyrophosphate + NAD(P)H → Squalene + Pyrophosphate + NAD(P)(+)details
Presqualene diphosphate + NADPH + Hydrogen Ion → Pyrophosphate + Squalene + NADPdetails
Farnesyl pyrophosphate + NADPH + Hydrogen Ion → Squalene + Pyrophosphate + NADPdetails
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
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DKFZp686B0215
Uniprot ID:
Q5HYI4
Molecular weight:
63793.4
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:
SEC14L3
Uniprot ID:
Q9UDX4
Molecular weight:
46047.8
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