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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 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?1600457008
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-75 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos210.86830932474
[M+H]+Not Available211.534http://allccs.zhulab.cn/database/detail?ID=AllCCS00000444
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+212.22830932474
DeepCCS[M-H]-209.8730932474
DeepCCS[M-2H]-244.10330932474
DeepCCS[M+Na]+219.33130932474
AllCCS[M+H]+217.432859911
AllCCS[M+H-H2O]+215.332859911
AllCCS[M+NH4]+219.432859911
AllCCS[M+Na]+219.932859911
AllCCS[M-H]-202.532859911
AllCCS[M+Na-2H]-204.232859911
AllCCS[M+HCOO]-206.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SqualeneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C3002.3Standard polar33892256
SqualeneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C2866.9Standard non polar33892256
SqualeneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C2860.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Squalene GC-MS (Non-derivatized)splash10-001i-9600000000-280b7ccaed0215f0937c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Squalene EI-B (Non-derivatized)splash10-015i-9500000000-63fc959bf17e2f6e03812017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Squalene GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dv-4879000000-3cfdaa630f73c021be062016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Squalene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0159-9610000000-aaf0145da95343082ae12015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Squalene Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-047r-1944600000-5faa7a5eb4804dfad2612019-11-13HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Squalene Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-4867900000-dcd3ba4f6ee550dc565b2019-11-13HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Squalene Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-2944400000-8be7743f6b07ba138c242019-11-13HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Squalene 20V, Positive-QTOFsplash10-03dj-2920300000-04f33a28f9d38283345e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 10V, Positive-QTOFsplash10-03di-0323900000-9162860711ec9f8266fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 20V, Positive-QTOFsplash10-02fx-2984100000-742302f14e45ce03bfdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 40V, Positive-QTOFsplash10-014l-6495000000-83c6df474790679c40e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 10V, Negative-QTOFsplash10-0a4i-0000900000-4905353fab78414bcab22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 20V, Negative-QTOFsplash10-0a4i-0000900000-e7195906634d18bf31dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 40V, Negative-QTOFsplash10-0006-1869100000-2d7d4eb74fe0c5856cbf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 10V, Positive-QTOFsplash10-03di-2844900000-f00046ef895fbe9888a32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 20V, Positive-QTOFsplash10-05mk-4928000000-3dfbc6d8fc1271828c3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 40V, Positive-QTOFsplash10-0a5j-4932000000-6f14fcc4a6e8029a16522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 10V, Negative-QTOFsplash10-0a4i-0000900000-45d1d2cb6b79e3bc92ae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 20V, Negative-QTOFsplash10-0a4i-0102900000-49aa25403f6062cc35202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Squalene 40V, Negative-QTOFsplash10-002o-1239000000-809fbf3fc0f0117fe5d12021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2019-11-13Wishart LabView Spectrum
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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 IDSQUALENE
BiGG IDNot Available
Wikipedia LinkSqualene
METLIN IDNot Available
PubChem Compound638072
PDB IDNot Available
ChEBI ID15440
Food Biomarker OntologyNot Available
VMH IDSQL
MarkerDB IDNot Available
Good Scents 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