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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:07:06 UTC
Update Date2022-03-07 02:55:07 UTC
HMDB IDHMDB0036930
Secondary Accession Numbers
  • HMDB36930
Metabolite Identification
Common NameGrandiflorolic acid
Descriptiondelta-Carotene-1,2-epoxide belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone. delta-Carotene-1,2-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862951
Synonyms
ValueSource
Δ-carotene-1,2-epoxideGenerator
1',2'-Epoxy-1',2'-dihydro-e,y-caroteneHMDB
1',2'-Epoxy-1',2'-dihydro-epsilon,psi-caroteneHMDB
D-Carotene-1,2-epoxideHMDB
Gradifloric acidHMDB
Grandifloric acidHMDB
15-Hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylateGenerator
GrandiflorolateGenerator
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name15-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
Traditional Name15-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
CAS Registry Number22338-69-8
SMILES
CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)
InChI KeyGVGJRXSJJHLPGZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point216 - 218 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.29ALOGPS
logP3.73ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.7ChemAxon
pKa (Strongest Basic)-0.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.73 m³·mol⁻¹ChemAxon
Polarizability36.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.29331661259
DarkChem[M-H]-171.45231661259
DeepCCS[M-2H]-212.68630932474
DeepCCS[M+Na]+188.25130932474
AllCCS[M+H]+180.132859911
AllCCS[M+H-H2O]+177.232859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.532859911
AllCCS[M-H]-183.632859911
AllCCS[M+Na-2H]-183.832859911
AllCCS[M+HCOO]-184.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Grandiflorolic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O3270.5Standard polar33892256
Grandiflorolic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O2471.8Standard non polar33892256
Grandiflorolic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O2641.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Grandiflorolic acid,1TMS,isomer #1C=C1C2CCC3C4(C)CCCC(C)(C(=O)O)C4CCC3(C2)C1O[Si](C)(C)C2663.6Semi standard non polar33892256
Grandiflorolic acid,1TMS,isomer #2C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C)C4CCC3(C2)C1O2569.7Semi standard non polar33892256
Grandiflorolic acid,2TMS,isomer #1C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C)C4CCC3(C2)C1O[Si](C)(C)C2538.0Semi standard non polar33892256
Grandiflorolic acid,1TBDMS,isomer #1C=C1C2CCC3C4(C)CCCC(C)(C(=O)O)C4CCC3(C2)C1O[Si](C)(C)C(C)(C)C2897.5Semi standard non polar33892256
Grandiflorolic acid,1TBDMS,isomer #2C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C4CCC3(C2)C1O2839.1Semi standard non polar33892256
Grandiflorolic acid,2TBDMS,isomer #1C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C4CCC3(C2)C1O[Si](C)(C)C(C)(C)C3033.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Grandiflorolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0293000000-6d81233578562a5d26aa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Grandiflorolic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0092-7057900000-207d915177a4f066ae382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Grandiflorolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Positive-QTOFsplash10-0uxr-0049000000-4b652304c7d71bce7fda2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Positive-QTOFsplash10-0zfr-0295000000-15eccd134beb9a35a29c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Positive-QTOFsplash10-0pvi-6891000000-4421f81b0af8e634e4432015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Negative-QTOFsplash10-014i-0069000000-718245f7e353ddb6470b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Negative-QTOFsplash10-0601-0093000000-1abaaf43e0d70f3166242015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Negative-QTOFsplash10-0ab9-0091000000-e4fe010c6ed57c8ce4f12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Negative-QTOFsplash10-014i-0009000000-4f15395cbd12cf9308a02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Negative-QTOFsplash10-014i-3059000000-ecaac400571ca670ba512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Positive-QTOFsplash10-00xr-0095000000-f5b39e03f542c252d9d42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Positive-QTOFsplash10-0ar3-0192000000-43f487add55056118e002021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Positive-QTOFsplash10-0670-2930000000-eb189dd440146f16ff222021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB015895
KNApSAcK IDC00022936
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752096
PDB IDNot Available
ChEBI IDNot Available
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.