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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:22:14 UTC
Update Date2022-03-07 02:56:02 UTC
HMDB IDHMDB0039018
Secondary Accession Numbers
  • HMDB39018
Metabolite Identification
Common NameApo-10'-violaxanthal
DescriptionApo-10'-violaxanthal belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Based on a literature review a small amount of articles have been published on Apo-10'-violaxanthal.
Structure
Data?1563863298
Synonyms
ValueSource
(3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-10'-apo-beta,psi-carotenalHMDB
10'-ApoviolaxanthalHMDB
5,6-Epoxy-3-hydroxy-5,6-dihydro-10'-apo-b-caroten-10'-alHMDB
5,6-Epoxy-5,6-dihydro-3-hydroxy-10'-apo-b,y-carotenal, 9ciHMDB
ApoviolaxanthinalHMDB
Chemical FormulaC27H36O3
Average Molecular Weight408.5729
Monoisotopic Molecular Weight408.266445018
IUPAC Name(2Z,4Z,6E,8E,10E,12Z,14E)-15-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenal
Traditional Name(2Z,4Z,6E,8E,10E,12Z,14E)-15-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenal
CAS Registry Number17237-68-2
SMILES
C\C(\C=C/C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C
InChI Identifier
InChI=1S/C27H36O3/c1-21(11-7-8-12-22(2)15-10-18-28)13-9-14-23(3)16-17-27-25(4,5)19-24(29)20-26(27,6)30-27/h7-18,24,29H,19-20H2,1-6H3/b8-7+,13-9+,15-10-,17-16+,21-11+,22-12-,23-14-
InChI KeyQZOYIQGWDBXSHB-AFMCRXATSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Oxepane
  • Alpha,beta-unsaturated aldehyde
  • Cyclic alcohol
  • Enal
  • Secondary alcohol
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aldehyde
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.004 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP6.28ALOGPS
logP4.75ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity132.46 m³·mol⁻¹ChemAxon
Polarizability48.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.82731661259
DarkChem[M-H]-204.81931661259
DeepCCS[M-2H]-239.57630932474
DeepCCS[M+Na]+215.030932474
AllCCS[M+H]+210.132859911
AllCCS[M+H-H2O]+207.732859911
AllCCS[M+NH4]+212.332859911
AllCCS[M+Na]+212.932859911
AllCCS[M-H]-204.832859911
AllCCS[M+Na-2H]-206.532859911
AllCCS[M+HCOO]-208.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Apo-10'-violaxanthalC\C(\C=C/C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C4801.6Standard polar33892256
Apo-10'-violaxanthalC\C(\C=C/C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C3321.1Standard non polar33892256
Apo-10'-violaxanthalC\C(\C=C/C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C3388.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Apo-10'-violaxanthal,1TMS,isomer #1CC(/C=C\C=O)=C/C=C/C=C(C)/C=C/C=C(C)\C=C\C12OC1(C)CC(O[Si](C)(C)C)CC2(C)C3426.4Semi standard non polar33892256
Apo-10'-violaxanthal,1TBDMS,isomer #1CC(/C=C\C=O)=C/C=C/C=C(C)/C=C/C=C(C)\C=C\C12OC1(C)CC(O[Si](C)(C)C(C)(C)C)CC2(C)C3647.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Apo-10'-violaxanthal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4009000000-788de8b2947c429a25f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apo-10'-violaxanthal GC-MS (1 TMS) - 70eV, Positivesplash10-014i-8623900000-b01066478e54c9126b6f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apo-10'-violaxanthal 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 - Apo-10'-violaxanthal 10V, Positive-QTOFsplash10-052f-1249300000-1a3b988a510e2aef6d112016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 20V, Positive-QTOFsplash10-007c-3963000000-b09f075dbaafcae0d3f52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 40V, Positive-QTOFsplash10-0a5j-9720000000-2e0cba0e08b61a17690e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 10V, Negative-QTOFsplash10-0a4i-0003900000-2c843a27ed5e156b5dc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 20V, Negative-QTOFsplash10-0a4r-1109700000-5acba32f13abcb4cf0052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 40V, Negative-QTOFsplash10-052f-7709000000-0dca8c35aa37d1a9f0fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 10V, Positive-QTOFsplash10-0006-0209100000-ec8e90b551dc114ebc562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 20V, Positive-QTOFsplash10-05tf-2449200000-083d698dd4879847f5262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 40V, Positive-QTOFsplash10-014l-3910000000-a2d8f58a39d43d19c9542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 10V, Negative-QTOFsplash10-014i-0109200000-fe4f3635ae2bf125e3852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 20V, Negative-QTOFsplash10-0a4i-1309500000-d3aa2bbc8a68cebded1a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-10'-violaxanthal 40V, Negative-QTOFsplash10-0002-0219000000-80410fe67edae88c6cbf2021-09-22Wishart 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 IDFDB018513
KNApSAcK IDC00023126
Chemspider ID35014717
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752515
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1873561
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.