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Record Information
Version2.0
Created at2024-09-10 19:35:34 UTC
Updated at2024-09-10 19:35:34 UTC
NP-MRD IDNP0334702
Secondary Accession NumbersNone
Natural Product Identification
Common Nameall-trans-phytoene
DescriptionPhytoene, also known as (all-e)-phytoene or trans-phytoene, 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. Thus, phytoene is considered to be an isoprenoid lipid molecule. The all-trans-isomer of phytoene. Phytoene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Phytoene exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Phytoene has been detected, but not quantified in, several different foods, such as sweet bay, jicama, highbush blueberries, butternut squash, and capers. all-trans-phytoene was first documented in 2005 (PMID: 15705230). This could make phytoene a potential biomarker for the consumption of these foods (PMID: 23144136).
Structure
Thumb
Synonyms
ValueSource
(6E,10E,14E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaeneChEBI
7,7',8,8',11,11',12,12'-Octahydro-psi,psi-caroteneChEBI
(all-e)-PhytoeneHMDB
all-trans-7,7',8,8',11,11',12,12'-Octahydro-lycopeneHMDB
all-trans-PhytoeneHMDB
trans-PhytoeneHMDB
(all-e) PhytoeneHMDB
7,7',8,8',11,11',12,12'-Octahydro-ψ,ψ-caroteneHMDB
7,7’,8,8’,11,11’,12,12’-octahydro-ψ,ψ-caroteneHMDB
Chemical FormulaC40H64
Average Mass544.9362 Da
Monoisotopic Mass544.50080 Da
IUPAC Name(6E,10E,14E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
Traditional Namephytoene
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C40H64/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/h11-12,19-22,27-30H,13-18,23-26,31-32H2,1-10H3/b12-11+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
InChI KeyYVLPJIGOMTXXLP-KEKOKYSKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.6ALOGPS
logP13.38ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity193.34 m³·mol⁻¹ChemAxon
Polarizability74.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002181
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030667
KNApSAcK IDC00000905
Chemspider ID4444344
KEGG Compound IDC05413
BioCyc IDPHYTOENE
BiGG IDNot Available
Wikipedia LinkPhytoene
METLIN IDNot Available
PubChem Compound5280784
PDB IDNot Available
ChEBI ID8191
Good Scents IDNot Available
References
General References
  1. Porrini M, Riso P, Brusamolino A, Berti C, Guarnieri S, Visioli F: Daily intake of a formulated tomato drink affects carotenoid plasma and lymphocyte concentrations and improves cellular antioxidant protection. Br J Nutr. 2005 Jan;93(1):93-9. doi: 10.1079/bjn20041315. [PubMed:15705230 ]
  2. Song GH, Kim SH, Choi BH, Han SJ, Lee PC: Heterologous carotenoid-biosynthetic enzymes: functional complementation and effects on carotenoid profiles in Escherichia coli. Appl Environ Microbiol. 2013 Jan;79(2):610-8. doi: 10.1128/AEM.02556-12. Epub 2012 Nov 9. [PubMed:23144136 ]