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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:16 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0002871
Secondary Accession Numbers
  • HMDB0002936
  • HMDB02871
  • HMDB02936
Metabolite Identification
Common NamePhytofluene
DescriptionPhytofluene, also known as (15Z)-phytofluene, belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Based on a literature review a small amount of articles have been published on Phytofluene.
Structure
Data?1582752257
Synonyms
ValueSource
(12E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaeneChEBI
(15Z)-PhytoflueneHMDB
15-cis-7,7',8,8',11,12-Hexahydro-psi,psi-caroteneHMDB
15-cis-7,7',8,8',11,12-Hexahydro-ψ,ψ-caroteneHMDB
15-cis-7,7’,8,8’,11,12-hexahydro-ψ,ψ-caroteneHMDB
15-cis-PhytoflueneHMDB
7,7',8,8',11,12-Hexahydro-psi,psi-caroteneHMDB
7,7',8,8',11,12-Hexahydro-ψ,ψ-caroteneHMDB
7,7',8,8',11,12-HexahydrolycopeneHMDB
7,7’,8,8’,11,12-hexahydro-ψ,ψ-caroteneHMDB
7,7’,8,8’,11,12-hexahydrolycopeneHMDB
cis-PhytoflueneHMDB
PhytoflueneChEBI
Chemical FormulaC40H62
Average Molecular Weight542.9203
Monoisotopic Molecular Weight542.485151984
IUPAC Name(6E,10E,12E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene
Traditional Namephytofluene
CAS Registry Number27664-65-9
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=C/C=C(\C)/C=C/C=C(\C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C40H62/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15,19-22,25,27-30H,13-14,16-18,23-24,26,31-32H2,1-10H3/b12-11-,25-15+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
InChI KeyOVSVTCFNLSGAMM-DGFSHVNOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentCarotenes
Alternative Parents
Substituents
  • Carotene
  • 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
ProcessNot Available
RoleNot 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 Solubility0.00036 g/LALOGPS
logP9.56ALOGPS
logP13.02ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity194.46 m³·mol⁻¹ChemAxon
Polarizability73.38 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
DarkChem[M+H]+238.23931661259
DarkChem[M-H]-231.46331661259
DeepCCS[M+H]+246.96230932474
DeepCCS[M-H]-244.56730932474
DeepCCS[M-2H]-277.74930932474
DeepCCS[M+Na]+252.87530932474
AllCCS[M+H]+242.632859911
AllCCS[M+H-H2O]+241.132859911
AllCCS[M+NH4]+244.032859911
AllCCS[M+Na]+244.432859911
AllCCS[M-H]-233.832859911
AllCCS[M+Na-2H]-236.332859911
AllCCS[M+HCOO]-239.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhytoflueneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=C/C=C(\C)/C=C/C=C(\C)CC\C=C(/C)CCC=C(C)C4287.3Standard polar33892256
PhytoflueneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=C/C=C(\C)/C=C/C=C(\C)CC\C=C(/C)CCC=C(C)C4046.5Standard non polar33892256
PhytoflueneCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=C/C=C(\C)/C=C/C=C(\C)CC\C=C(/C)CCC=C(C)C3880.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phytofluene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adr-6737950000-5bc097f55616a51c69f92017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 10V, Positive-QTOFsplash10-0006-0232290000-40fbdad25d3a9f72f7c62017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 20V, Positive-QTOFsplash10-0k9f-1795610000-ee6f8f065adbed64eaf12017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 40V, Positive-QTOFsplash10-00ku-3598700000-4dc8949deb3be611e25b2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 10V, Negative-QTOFsplash10-0006-0000090000-df37ad38dbbff70a66212017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 20V, Negative-QTOFsplash10-0006-0000090000-2dfd6018e8fd64f574602017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 40V, Negative-QTOFsplash10-056r-1696680000-8973766effda26e10e0f2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 10V, Positive-QTOFsplash10-0006-2440790000-9fe59830abb813a3451f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 20V, Positive-QTOFsplash10-0f89-2111920000-97631f9f62b37a12abf52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 40V, Positive-QTOFsplash10-069a-1342900000-09728872dac5a380e48a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 10V, Negative-QTOFsplash10-0006-0000090000-3f653aa7784c4801973f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 20V, Negative-QTOFsplash10-0006-0140190000-50e2dd4ff360e6de7fc72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytofluene 40V, Negative-QTOFsplash10-0adi-1502910000-2740ef4a93a3f6efd3a82021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.085 +/- 0.057 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.302 +/- 0.024 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.23 +/- 0.10 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.37 +/- 0.17 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022937
KNApSAcK IDC00000913
Chemspider ID5256893
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhytofluene
METLIN IDNot Available
PubChem Compound6857557
PDB IDNot Available
ChEBI ID35165
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aust O, Stahl W, Sies H, Tronnier H, Heinrich U: Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema. Int J Vitam Nutr Res. 2005 Jan;75(1):54-60. [PubMed:15830922 ]
  2. Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. [PubMed:1416048 ]
  3. Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. [PubMed:15003396 ]