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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:27 UTC
Update Date2021-09-14 15:41:46 UTC
HMDB IDHMDB0003023
Secondary Accession Numbers
  • HMDB03023
Metabolite Identification
Common NamePrephytoene diphosphate
DescriptionPhytoene is a precursor to carotenoids. Prephytoene comes from geranyl geranyl diphosphate (GGPP). Carotenoids are essential for life. Prephytoene diphosphate is involved in the following two reactions: 1) Prephytoene diphosphate + H+ + NADPH <=> Pyrophosphate + cis-Phytoene + NADP+ and 2) Geranylgeranyl diphosphate <=> Pyrophosphate + Prephytoene diphosphate + H+.
Structure
Data?1592863006
Synonyms
ValueSource
Prephytoene diphosphoric acidGenerator
Prelycopersene pyrophosphateMeSH, HMDB
Prephytoene pyrophosphateMeSH, HMDB
Chemical FormulaC40H68O7P2
Average Molecular Weight722.9112
Monoisotopic Molecular Weight722.444027554
IUPAC Name{[hydroxy({[(1R,2R,3R)-2-methyl-3-[(1E,5E,9E)-2,6,10,14-tetramethylpentadeca-1,5,9,13-tetraen-1-yl]-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclopropyl]methoxy})phosphoryl]oxy}phosphonic acid
Traditional Nameprephytoene diphosphate
CAS Registry Number38005-61-7
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)[C@]1(C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C40H68O7P2/c1-31(2)17-11-19-33(5)21-13-23-35(7)25-15-26-37(9)29-38-39(30-46-49(44,45)47-48(41,42)43)40(38,10)28-16-27-36(8)24-14-22-34(6)20-12-18-32(3)4/h17-18,21-22,25,27,29,38-39H,11-16,19-20,23-24,26,28,30H2,1-10H3,(H,44,45)(H2,41,42,43)/b33-21+,34-22+,35-25+,36-27+,37-29+/t38-,39-,40-/m1/s1
InChI KeyRVCNKTPCHZNAAO-UZDKSQMHSA-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
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP7.02ALOGPS
logP11.32ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity212.94 m³·mol⁻¹ChemAxon
Polarizability84.57 ųChemAxon
Number of Rings1ChemAxon
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]+253.8830932474
DeepCCS[M-H]-252.21430932474
DeepCCS[M-2H]-286.24930932474
DeepCCS[M+Na]+260.02430932474
AllCCS[M+H]+275.432859911
AllCCS[M+H-H2O]+274.332859911
AllCCS[M+NH4]+276.332859911
AllCCS[M+Na]+276.632859911
AllCCS[M-H]-261.932859911
AllCCS[M+Na-2H]-267.432859911
AllCCS[M+HCOO]-273.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prephytoene diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)[C@]1(C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C5036.8Standard polar33892256
Prephytoene diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)[C@]1(C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C4024.1Standard non polar33892256
Prephytoene diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)[C@]1(C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C4654.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prephytoene diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4568.1Semi standard non polar33892256
Prephytoene diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C3852.3Standard non polar33892256
Prephytoene diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C5643.1Standard polar33892256
Prephytoene diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4579.2Semi standard non polar33892256
Prephytoene diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C3863.5Standard non polar33892256
Prephytoene diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C5686.6Standard polar33892256
Prephytoene diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4509.1Semi standard non polar33892256
Prephytoene diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C3883.0Standard non polar33892256
Prephytoene diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C5116.5Standard polar33892256
Prephytoene diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4501.9Semi standard non polar33892256
Prephytoene diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C3868.9Standard non polar33892256
Prephytoene diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C5120.1Standard polar33892256
Prephytoene diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4755.3Semi standard non polar33892256
Prephytoene diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C3995.9Standard non polar33892256
Prephytoene diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C5672.9Standard polar33892256
Prephytoene diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4748.1Semi standard non polar33892256
Prephytoene diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C4012.0Standard non polar33892256
Prephytoene diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@]1(C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C5712.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prephytoene diphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbi-3310095300-57d54a56347e62d17d242017-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 10V, Positive-QTOFsplash10-0095-1110098500-2c32df8783f51fa23d492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 20V, Positive-QTOFsplash10-0002-2121290000-cc1961830b6d15c325132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 40V, Positive-QTOFsplash10-052e-2222492000-c5a5555cf9eeb4e186a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 10V, Negative-QTOFsplash10-00fr-0500000900-452dd811e6d127aa1c462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 20V, Negative-QTOFsplash10-01t9-9200010000-61664436d6a72f8754282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-82412cff79d2ea55320d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 10V, Positive-QTOFsplash10-023a-3020859600-8b4618e11e8d9550bd542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 20V, Positive-QTOFsplash10-0gx9-2200059000-6fa5c0f2652df16dae502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 40V, Positive-QTOFsplash10-05nr-3312493000-38ff2bcb3b9a44b6c0ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 10V, Negative-QTOFsplash10-00di-0000000900-93a30b275a9dd5f87f832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 20V, Negative-QTOFsplash10-00di-1400011900-eae8906b61c363457dab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephytoene diphosphate 40V, Negative-QTOFsplash10-0a6r-5900000000-912bad49cc42f7aa92742021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023095
KNApSAcK IDNot Available
Chemspider ID21864822
KEGG Compound IDC03427
BioCyc IDCPD-464
BiGG IDNot Available
Wikipedia LinkPrephytoene diphosphate
METLIN ID3592
PubChem Compound24883415
PDB IDNot Available
ChEBI ID17090
Food Biomarker OntologyNot Available
VMH IDPPHTD
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGregonis, Donald E.; Rilling, Hans C. Stereochemistry of trans-phytoene synthesis. Lycopersene as a carotene precursor and a mechanism for the synthesis of cis- and trans-phytoene. Biochemistry (1974), 13(7), 1538-42.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Muller H, Bub A, Watzl B, Rechkemmer G: Plasma concentrations of carotenoids in healthy volunteers after intervention with carotenoid-rich foods. Eur J Nutr. 1999 Feb;38(1):35-44. [PubMed:10338686 ]
  2. Zhu YH, Jiang JG, Yan Y, Chen XW: Isolation and characterization of phytoene desaturase cDNA involved in the beta-carotene biosynthetic pathway in Dunaliella salina. J Agric Food Chem. 2005 Jul 13;53(14):5593-7. [PubMed:15998120 ]