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Showing Compound Geranylgeraniol (FDB001528)

Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:34 UTC
Primary IDFDB001528
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGeranylgeraniol
DescriptionGeranylgeraniol, also known as tetraprenol or (2e,6e,10e)-geranylgeraniol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeraniol is considered to be an isoprenoid lipid molecule. Geranylgeraniol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Geranylgeraniol can be found in flaxseed, which makes geranylgeraniol a potential biomarker for the consumption of this food product. Geranylgeraniol is a diterpene alcohol which plays a role in several important biological processes. It is an intermediate in the biosynthesis of other diterpenes and of vitamins E and K. It also used in the post-translational modification known as geranylgeranylation. Geranylgeraniol is a pheromone for bumblebees and a variety of other insects .
CAS Number24034-73-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2E,6E,10E)-GeranylgeraniolChEBI
Geranylgeraniol, (e,e,e)-isomerMeSH
Geranylgeraniol, (Z,Z,Z)-isomerMeSH
TetraprenolMeSH
(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-olPhytoBank
(E,E,E)-GeranylgeraniolPhytoBank
(E,E,E)-Geranylgeranyl alcoholPhytoBank
All-trans-GeranylgeraniolPhytoBank
GeranylgeraniolPhytoBank
Geranylgeranyl alcoholPhytoBank
trans,trans,trans-GeranylgeraniolPhytoBank
trans-GeranylgeraniolPhytoBank
(e,e,e)-geranylgeraniolbiospider
2,6,10,14-hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-biospider
All-trans-geranylgeraniolbiospider
Gernaylgeraniolbiospider
Trans-geranylgeraniolbiospider
Trans,trans,trans-geranylgeraniolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP6.06ALOGPS
logP5.82ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity98.79 m³·mol⁻¹ChemAxon
Polarizability38.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O
IUPAC name(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol
InChI IdentifierInChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
InChI KeyOJISWRZIEWCUBN-QIRCYJPOSA-N
Isomeric SMILES[H]\C(CO)=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C
Average Molecular Weight290.4834
Monoisotopic Molecular Weight290.26096571
Classification
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Long chain fatty alcohol
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-9300000000-1ee3bddd85e9086b7517Spectrum
Predicted GC-MSGeranylgeraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-6590000000-d53875d1d1717d638752Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0290000000-406439b04dab8ae9f72aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-4970000000-f76480cde6f70f69904fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-9730000000-6885c45bb706a217604bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-ae922ee5b3568def3a2bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-bd08abbb2b7066c4796aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-3590000000-59768ae8b64336ff3df0Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09094
Pubchem Compound ID5281365
Pubchem Substance IDNot Available
ChEBI ID46762
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGERANYL-GERANIOL
BIGG IDNot Available
KNApSAcK IDC00003428
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti adenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti proliferantDUKE
apoptoticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
protisticideDUKE
schistosomicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.