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Human Metabolome Database Version 2.5

 

Showing metabocard for (S)-2,3-Epoxysqualene (HMDB01188)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:37
Accession Number HMDB01188
Secondary Accession Numbers Not Available
Common Name (S)-2,3-Epoxysqualene
Description (S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Squalene monooxygenase and Lanosterol synthase.
Synonyms
  1. (S)-2,3-Epoxysqualene
  2. (S)-Squalene-2,3-epoxide
  3. Squalene 2,3-epoxide
  4. Squalene 2,3-oxide
Chemical IUPAC Name 2,2-dimethyl-3-(3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaenyl)oxirane
Chemical Formula C30H50O
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellanous
Class
  • Alkanes and Alkenes
Sub Class
  • Long chain alkenes
Family
  • Mammalian Metabolite
Species
  • dialkyl ether
  • alkene
  • heterocyclic compound
Biofunction
  • Component of Terpenoid biosynthesis
Application
—
Source
  • Endogenous
Average Molecular Weight 426.717
Monoisotopic Molecular Weight 426.386169
Isomeric SMILES CC(C)=CCCC(C)=CCCC(C)=C/CCC=C(/C)CCC=C(C)CC[C@@H]1OC1(C)C
Canonical SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC1OC1(C)C
KEGG Compound ID C01054 Link Image
BioCyc ID EPOXYSQUALENE Link Image
BiGG ID 36708 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01188 Link Image
Metagene Link HMDB01188 Link Image
METLIN ID 3530 Link Image
PubChem Compound 439382 Link Image
PubChem Substance 4295 Link Image
ChEBI ID 15441 Link Image
CAS Registry Number 9029-62-3
InChI Identifier InChI=1/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15-,26-16+,27-20+,28-21-/t29-/m0/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 4.16e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 8.58 [Predicted by ALOGPS]; 7.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • endoplasmic reticulum
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Steroid Biosynthesis SMP00023 Link Image map00100 Link Image
General References Not Available
Metabolic Enzymes
  1. Lanosterol synthase
  2. Putative uncharacterized protein DKFZp686B0215
Enzyme 1 [top]
Enzyme 1 ID 5667
Enzyme 1 Name Lanosterol synthase
Enzyme 1 Synonyms
  1. Oxidosqualene--lanosterol cyclase
  2. 2,3-epoxysqualene--lanosterol cyclase
  3. OSC
Enzyme 1 Gene Name LSS
Enzyme 1 Protein Sequence >Lanosterol synthase 
MTEGTCLRRRGGPYKTEPATDLGRWRLNCERGRQTWTYLQDERAGREQTGLEAYALGLDT
KNYFKDLPKAHTAFEGALNGMTFYVGLQAEDGHWTGDYGGPLFLLPGLLITCHVARIPLP
AGYREEIVRYLRSVQLPDGGWGLHIEDKSTVFGTALNYVSLRILGVGPDDPDLVRARNIL
HKKGGAVAIPSWGKFWLAVLNVYSWEGLNTLFPEMWLFPDWAPAHPSTLWCHCRQVYLPM
SYCYAVRLSAAEDPLVQSLRQELYVEDFASIDWLAQRNNVAPDELYTPHSWLLRVVYALL
NLYEHHHSAHLRQRAVQKLYEHIVADDRFTKSISIGPISKTINMLVRWYVDGPASTAFQE
HVSRIPDYLWMGLDGMKMQGTNGSQIWDTAFAIQALLEAGGHHRPEFSSCLQKAHEFLRL
SQVPDNPPDYQKYYRQMRKGGFSFSTLDCGWIVSDCTAEALKAVLLLQEKCPHVTEHIPR
ERLCDAVAVLLNMRNPDGGFATYETKRGGHLLELLNPSEVFGDIMIDYTYVECTSAVMQA
LKYFHKRFPEHRAAEIRETLTQGLEFCRRQQRADGSWEGSWGVCFTYGTWFGLEAFACMG
QTYRDGTACAEVSRACDFLLSRQMADGGWGEDFESCEERRYLQSAQSQIHNTCWAMMGLM
AVRHPDIEAQERGVRCLLEKQLPNGDWPQENIAGVFNKSCAISYTSYRNIFPIWALGRFS
QLYPERALAGHP
Enzyme 1 Number of Residues 732
Enzyme 1 Molecular Weight 83310
Enzyme 1 Theoretical pI 6.60
Enzyme 1 GO Classification
Function
  • catalytic activity
  • lyase activity
Process
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Translation, ribosomal structure and biogenesis
Enzyme 1 Specific Function Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus
Enzyme 1 Pathways
Enzyme 1 Reactions
  • (S)-2,3-epoxysqualene = lanosterol
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 951314 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P48449 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name ERG7_HUMAN Link Image
Enzyme 1 PDB ID 1W6J Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >2199 bp 
ATGACGGAGGGCACGTGTCTGCGGCGCCGAGGGGGCCCCTACAAGACCGAGCCCGCCACC
GACCTCGGCCGCTGGCGACTCAACTGCGAGAGGGGCCGGCAGACGTGGACCTACCTGCAG
GACGAGCGCGCCGGCCGCGAGCAGACCGGCCTGGAAGCCTACGCCCTGGGGCTGGACACC
AAGAATTACTTTAAGGACTTGCCCAAAGCCCACACCGCCTTTGAGGGGGCTCTGAACGGG
ATGACATTTTACGTGGGGCTGCAGGCTGAGGATGGGCACTGGACGGGTGATTATGGTGGC
CCACTTTTCCTCCTGCCAGGCCTCCTGATCACTTGCCACGTGGCACGCATCCCTCTGCCA
GCCGGATACAGAGAAGAGATTGTGCGGTACCTGCGGTCAGTGCAGCTCCCTGACGGTGGC
TGGGGCCTGCACATTGAGGATAAGTCCACCGTGTTTGGGACTGCGCTCAACTATGTGTCT
CTCAGAATTCTGGGTGTTGGGCCTGACGATCCTGACCTGGTACGAGCCCGGAACATTCTT
CACAAGAAAGGTGGTGCTGTGGCCATCCCCTCCTGGGGGAAGTTCTGGCTGGCTGTCCTG
AATGTTTACAGCTGGGAAGGCCTCAATACCCTGTTCCCAGAGATGTGGCTGTTTCCTGAC
TGGGCACCGGCACACCCCTCCACACTCTGGTGCCACTGCCGGCAGGTGTACCTGCCCATG
AGCTACTGCTACGCCGTTCGGCTGAGTGCCGCGGAAGACCCGCTGGTCCAGAGCCTCCGC
CAGGAGCTCTATGTGGAGGACTTCGCCAGCATTGACTGGCTGGCGCAGAGGAACAACGTG
GCCCCCGACGAGCTGTACACGCCCCACAGCTGGCTGCTCCGCGTGGTATATGCGCTCCTC
AACCTGTATGAGCACCACCACAGTGCCCACCTGCGGCAGCGGGCCGTGCAGAAGCTGTAT
GAACACATTGTGGCCGACGACCGATTCACCAAGAGCATCAGCATCGGCCCGATCTCGAAA
ACCATCAACATGCTTGTGCGCTGGTATGTGGACGGGCCCGCCTCCACTGCCTTCCAGGAG
CATGTCTCCAGAATCCCGGACTATCTCTGGATGGGCCTTGACGGCATGAAAATGCAGGGC
ACCAACGGCTCACAGATCTGGGACACCGCATTCGCCATCCAGGCTCTGCTTGAGGCGGGC
GGGCACCACAGGCCCGAGTTTTCGTCCTGCCTGCAGAAGGCTCATGAGTTCCTGAGGCTC
TCACAGGTCCCAGATAACCCTCCCGACTACCAGAAGTACTACCGCCAGATGCGCAAGGGT
GGCTTCTCCTTCAGTACGCTGGACTGCGGCTGGATCGTTTCTGACTGCACGGCTGAGGCC
TTGAAGGCTGTGCTGCTCCTGCAGGAGAAGTGTCCCCATGTCACCGAGCACATCCCCAGA
GAACGGCTCTGCGATGCTGTGGCTGTGCTGCTGAACATGAGAAATCCAGATGGAGGGTTC
GCCACCTATGAGACCAAGCGTGGGGGGCACTTGCTGGAGCTGCTGAACCCCTCGGAGGTC
TTCGGGGACATCATGATTGACTACACCTATGTGGAGTGCACCTCAGCCGTGATGCAGGCG
CTTAAGTATTTCCACAAGCGTTTCCCGGAGCACAGGGCAGCGGAGATCCGGGAGACCCTC
ACGCAGGGCTTAGAGTTCTGTCGGCGGCAGCAGAGGGCCGATGGCTCCTGGGAAGGCTCC
TGGGGAGTTTGCTTCACCTACGGCACCTGGTTTGGCCTGGAGGCCTTCGCCTGTATGGGG
CAGACCTACCGAGATGGGACTGCCTGTGCAGAGGTCTCCCGGGCCTGTGACTTCCTGCTG
TCCCGGCAGATGGCAGACGGAGGCTGGGGGGAGGACTTTGAGTCCTGCGAGGAGCGGCGT
TATTTGCAGAGTGCCCAGTCCCAGATCCATAACACATGCTGGGCCATGATGGGGCTGATG
GCCGTTCGGCATCCTGACATCGAGGCCCAGGAGAGAGGAGTCCGGTGTCTACTTGAGAAA
CAGCTCCCCAATGGCGACTGGCCGCAGGAAAACATTGCTGGGGTCTTCAACAAGTCCTGT
GCCATCTCCTACACGAGCTACAGGAACATCTTCCCCATCTGGGCCCTCGGCCGCTTCTCC
CAGCTGTACCCTGAGAGAGCCCTTGCTGGCCACCCCTGA
Enzyme 1 GenBank Gene ID U22526 Link Image
Enzyme 1 GeneCard ID LSS Link Image
Enzyme 1 GenAtlas ID LSS Link Image
Enzyme 1 HGNC ID HGNC:6708 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Baker CH, Matsuda SP, Liu DR, Corey EJ: Molecular cloning of the human gene encoding lanosterol synthase from a liver cDNA library. Biochem Biophys Res Commun. 1995 Aug 4;213(1):154-60. [PubMed Link Image]
  2. Sung CK, Shibuya M, Sankawa U, Ebizuka Y: Molecular cloning of cDNA encoding human lanosterol synthase. Biol Pharm Bull. 1995 Oct;18(10):1459-61. [PubMed Link Image]
  3. Roessler E, Mittaz L, Du Y, Scott HS, Chang J, Rossier C, Guipponi M, Matsuda SP, Muenke M, Antonarakis SE: Structure of the human Lanosterol synthase gene and its analysis as a candidate for holoprosencephaly (HPE1). Hum Genet. 1999 Nov;105(5):489-95. [PubMed Link Image]
  4. Young M, Chen H, Lalioti MD, Antonarakis SE: The human lanosterol synthase gene maps to chromosome 21q22.3. Hum Genet. 1996 May;97(5):620-4. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 13008
Enzyme 2 Name Putative uncharacterized protein DKFZp686B0215
Enzyme 2 Synonyms Not Available
Enzyme 2 Gene Name DKFZp686B0215
Enzyme 2 Protein Sequence >Putative uncharacterized protein DKFZp686B0215 
MWTFLGIATFTYFYKKFGDFITLANREVLLCVLVFLSLGLVLSYRCRHRNGGLLGRQQSG
SQFALFSDILSGLPFIGFFWAKSPPESENKEQLEARRRRKGTNISETSLIGTAACTSTSS
QNDPEVIIVGAGVLGSALAAVLSRDGRKVTVIERDLKEPDRIVGEFLQPGGYHVLKDLGL
GDTVEGLDAQVVNGYMIHDQESKSEVQIPYPLSENNQVQSGRAFHHGRFIMSLRKAAMAE
PNAKFIEGVVLQLLEEDDVVMGVQYKDKETGDIKELHAPLTVVADGLFSKFRKSLVSNKV
SVSSHFVGFLMKNAPQFKANHAELILANPGPVLIYQISSSETRVLVDIRGEMPRNLREYM
VEKIYPQIPDHLKEPFLEATDNSHLRSMPASFLPPSSVKKRGVLLLGDAYNMRHPLTGGG
MTVAFKDIKLWRKLLKGIPDLYDDAAIFEAKKSFYWARKTSHSFVVNILAQALYELFSAT
DDSLHQLGKACFLYFKLGGECVAGPVGLLSVLSPNPLVLIGHFFAVAIYAVYFCFKSEPW
ITKPRALLSSGAVLYKACSVIFPLIYSEMKYMVH
Enzyme 2 Number of Residues 574
Enzyme 2 Molecular Weight 63795
Enzyme 2 Theoretical pI 8.73
Enzyme 2 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 2 General Function Coenzyme transport and metabolism
Enzyme 2 Specific Function Not Available
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 57997512 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q5HYI4 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name Q5HYI4_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID BX647605 Link Image
Enzyme 2 GeneCard ID Q5HYI4 Link Image
Enzyme 2 GenAtlas ID DKFZp686B0215 Link Image
Enzyme 2 HGNC ID HGNC:11279 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available