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Human Metabolome Database Version 2.5

 

Showing metabocard for Presqualene diphosphate (HMDB01278)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2010-05-07 09:22:33
Accession Number HMDB01278
Secondary Accession Numbers Not Available
Common Name Presqualene diphosphate
Description Presqualene diphosphate is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Farnesyl-diphosphate farnesyltransferase.
Synonyms
  1. (1alpha,2beta(E),3beta(1E,5E))-Diphosphoric acid mono((2-(4,8-dimethyl-3,7-nonadienyl)-2-methyl-3-(2,6,10-trimethyl-1,5,9-undecatrienyl)cyclopropyl)methyl) ester
  2. Presqualene diphosphate
  3. Presqualene diphosphic acid
  4. Presqualene pyrophosphate
Chemical IUPAC Name [[2-(4,8-dimethylnona-3,7-dienyl)-2-methyl-3-(2,6,10-trimethylundeca-1,5,9-trienyl)cyclopropyl]methoxy-hydroxy-phosphoryl]oxyphosphonic acid
Chemical Formula C30H52O7P2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellaneous
Class
  • Acyl Phosphates
Sub Class
  • Long chain acyl phosphates
Family
  • Mammalian Metabolite
Species
  • phosphoric acid ester
  • alkene
Biofunction
  • Component of Terpenoid biosynthesis
Application
—
Source
  • Endogenous
Average Molecular Weight 586.677
Monoisotopic Molecular Weight 586.318848
Isomeric SMILES CC(C)=CCCC(C)=CCCC(C)=C[C@H]1[C@H](COP(O)(=O)OP(O)(O)=O)[C@@]1(C)CCC=C(/C)CCC=C(C)C
Canonical SMILES CC(C)=CCCC(C)=CCCC(C)=CC1C(COP(O)(=O)OP(O)(O)=O)C1(C)CCC=C(C)CCC=C(C)C
KEGG Compound ID C03428 Link Image
BioCyc ID CPD-465 Link Image
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01278 Link Image
Metagene Link HMDB01278 Link Image
METLIN ID 6132 Link Image
PubChem Compound 6449797 Link Image
PubChem Substance 11971994 Link Image
ChEBI ID 15442 Link Image
CAS Registry Number 29849-75-0
InChI Identifier InChI=1/C30H52O7P2/c1-23(2)13-9-15-25(5)17-11-18-27(7)21-28-29(22-36-39(34,35)37-38(31,32)33)30(28,8)20-12-19-26(6)16-10-14-24(3)4/h13-14,17,19,21,28-29H,9-12,15-16,18,20,22H2,1-8H3,(H,34,35)(H2,31,32,33)/b25-17+,26-19+,27-21+/t28-,29-,30-/m0/s1
Synthesis Reference Rogers, Daniel H.; Yi, Eugene C.; Poulter, C. Dale. Enantioselective Synthesis of (+)-Presqualene Diphosphate. Journal of Organic Chemistry (1995), 60(4), 941-5.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.14e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -3
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.31 [Predicted by ALOGPS]; 4.838 [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
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
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. Squalene synthetase
Enzyme 1 [top]
Enzyme 1 ID 5492
Enzyme 1 Name Squalene synthetase
Enzyme 1 Synonyms
  1. SQS
  2. SS
  3. Farnesyl-diphosphate farnesyltransferase
  4. FPP:FPP farnesyltransferase
Enzyme 1 Gene Name FDFT1
Enzyme 1 Protein Sequence >Squalene synthetase 
MEFVKCLGHPEEFYNLVRFRIGGKRKVMPKMDQDSLSSSLKTCYKYLNQTSRSFAAVIQA
LDGEMRNAVCIFYLVLRALDTLEDDMTISVEKKVPLLHNFHSFLYQPDWRFMESKEKDRQ
VLEDFPTISLEFRNLAEKYQTVIADICRRMGIGMAEFLDKHVTSEQEWDKYCHYVAGLVG
IGLSRLFSASEFEDPLVGEDTERANSMGLFLQKTNIIRDYLEDQQGGREFWPQEVWSRYV
KKLGDFAKPENIDLAVQCLNELITNALHHIPDVITYLSRLRNQSVFNFCAIPQVMAIATL
AACYNNQQVFKGAVKIRKGQAVTLMMDATNMPAVKAIIYQYMEEIYHRIPDSDPSSSKTR
QIISTIRTQNLPNCQLISRSHYSPIYLSFVMLLAALSWQYLTTLSQVTEDYVQTGEH
Enzyme 1 Number of Residues 417
Enzyme 1 Molecular Weight 48116
Enzyme 1 Theoretical pI 6.51
Enzyme 1 GO Classification
Function
  • catalytic activity
  • farnesyl-diphosphate farnesyltransferase activity
  • farnesyltranstransferase activity
  • prenyltransferase activity
  • transferase activity
  • transferase activity, transferring alkyl or aryl (other than methyl) groups
Process
  • biosynthesis
  • lipid biosynthesis
  • metabolism
  • physiological process
Component
  • cell
  • integral to membrane
  • intrinsic to membrane
  • membrane
Enzyme 1 General Function Lipid transport and metabolism
Enzyme 1 Specific Function 2 farnesyl diphosphate = diphosphate + presqualene diphosphate
Enzyme 1 Pathways
Enzyme 1 Reactions
  • 2 farnesyl diphosphate = diphosphate + presqualene diphosphate
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • 284-304 384-404
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 292510 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P37268 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name FDFT_HUMAN Link Image
Enzyme 1 PDB ID 1EZF Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1254 bp 
ATGGAGTTCGTGAAATGCCTTGGCCACCCCGAAGAGTTCTACAACCTGGTGCGCTTCCGG
ATCGGGGGCAAGCGGAAGGTGATGCCCAAGATGGACCAGGACTCGCTCAGCAGCAGCCTG
AAAACTTGCTACAAGTATCTCAATCAGACCAGTCGCAGTTTCGCAGCTGTTATCCAGGCG
CTGGATGGGGAAATGCGCAACGCAGTGTGCATATTTTATCTGGTTCTCCGAGCTCTGGAC
ACACTGGAAGATGACATGACCATCAGTGTGGAAAAGAAGGTCCCGCTGTTACACAACTTT
CACTCTTTCCTTTACCAACCAGACTGGCGGTTCATGGAGAGCAAGGAGAAGGATCGCCAG
GTGCTGGAGGACTTCCCAACGATCTCCCTTGAGTTTAGAAATCTGGCTGAGAAATACCAA
ACAGTGATTGCCGACATTTGCCGGAGAATGGGCATTGGGATGGCAGAGTTTTTGGATAAG
CATGTGACCTCTGAACAGGAGTGGGACAAGTACTGCCACTATGTTGCTGGGCTGGTCGGA
ATTGGCCTTTCCCGTCTTTTCTCAGCCTCAGAGTTTGAAGACCCCTTAGTTGGTGAAGAT
ACAGAACGTGCCAACTCTATGGGCCTGTTTCTGCAGAAAACAAACATCATCCGTGACTAT
CTGGAAGACCAGCAAGGAGGAAGAGAGTTCTGGCCTCAAGAGGTTTGGAGCAGGTATGTT
AAGAAGTTAGGGGATTTTGCTAAGCCGGAGAATATTGACTTGGCCGTGCAGTGCCTGAAT
GAACTTATAACCAATGCACTGCACCACATCCCAGATGTCATCACCTACCTTTCGAGACTC
AGAAACCAGAGTGTGTTTAACTTCTGCGCTATTCCACAGGTGATGGCCATTGCCACTTTG
GCTGCCTGTTATAATAACCAGCAGGTGTTCAAAGGGGCAGTGAAGATTCGGAAAGGGCAA
GCAGTGACCCTGATGATGGATGCCACCAATATGCCAGCTGTCAAAGCCATCATATATCAG
TATATGGAAGAGATTTATCATAGAATCCCCGACTCAGACCCATCTTCTAGCAAAACAAGG
CAGATCATCTCCACCATCCGGACGCAGAATCTTCCCAACTGTCAGCTGATTTCCCGAAGC
CACTACTCCCCCATCTACCTGTCGTTTGTCATGCTTTTGGCTGCCCTGAGCTGGCAGTAC
CTGACCACTCTCTCCCAGGTAACAGAAGACTATGTTCAGACTGGAGAACACTGA
Enzyme 1 GenBank Gene ID L06070 Link Image
Enzyme 1 GeneCard ID FDFT1 Link Image
Enzyme 1 GenAtlas ID FDFT1 Link Image
Enzyme 1 HGNC ID HGNC:3629 Link Image
Enzyme 1 Chromosome Location 8
Enzyme 1 Locus 8p23.1-p22
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Robinson GW, Tsay YH, Kienzle BK, Smith-Monroy CA, Bishop RW: Conservation between human and fungal squalene synthetases: similarities in structure, function, and regulation. Mol Cell Biol. 1993 May;13(5):2706-17. [PubMed Link Image]
  2. Jiang G, McKenzie TL, Conrad DG, Shechter I: Transcriptional regulation by lovastatin and 25-hydroxycholesterol in HepG2 cells and molecular cloning and expression of the cDNA for the human hepatic squalene synthase. J Biol Chem. 1993 Jun 15;268(17):12818-24. [PubMed Link Image]
  3. Summers C, Karst F, Charles AD: Cloning, expression and characterisation of the cDNA encoding human hepatic squalene synthase, and its relationship to phytoene synthase. Gene. 1993 Dec 22;136(1-2Che):185-92. [PubMed Link Image]
  4. Soltis DA, McMahon G, Caplan SL, Dudas DA, Chamberlin HA, Vattay A, Dottavio D, Rucker ML, Engstrom RG, Cornell-Kennon SA, et al.: Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems. Arch Biochem Biophys. 1995 Feb 1;316(2):713-23. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available