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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:53:16 UTC
Update Date2022-03-07 02:54:17 UTC
HMDB IDHMDB0034953
Secondary Accession Numbers
  • HMDB34953
Metabolite Identification
Common NameApo-12'-violaxanthal
DescriptionApo-12'-violaxanthal belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a small amount of articles have been published on Apo-12'-violaxanthal.
Structure
Data?1563862641
Synonyms
ValueSource
5,6-Epoxy-5,6-dihydro-3b-hydroxy-12'-apo-b-caroten-12'-alHMDB
Chemical FormulaC25H34O3
Average Molecular Weight382.5357
Monoisotopic Molecular Weight382.250794954
IUPAC Name(2Z,4E,6E,8E,10Z,12E)-13-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal
Traditional Name(2Z,4E,6E,8E,10Z,12E)-13-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal
CAS Registry NumberNot Available
SMILES
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/C25H34O3/c1-19(10-7-8-11-21(3)18-26)12-9-13-20(2)14-15-25-23(4,5)16-22(27)17-24(25,6)28-25/h7-15,18,22,27H,16-17H2,1-6H3/b8-7+,12-9+,15-14+,19-10+,20-13-,21-11-
InChI KeyCAXVJDRXJFKYQP-RXCALXPUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Oxepane
  • Alpha,beta-unsaturated aldehyde
  • Cyclic alcohol
  • Enal
  • Secondary alcohol
  • Dialkyl ether
  • Oxacycle
  • Oxirane
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aldehyde
  • Organic oxygen compound
  • Organooxygen 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP5.84ALOGPS
logP4.37ChemAxon
logS-5ALOGPS
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 Count7ChemAxon
Refractivity122.22 m³·mol⁻¹ChemAxon
Polarizability46.14 ųChemAxon
Number of Rings2ChemAxon
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]+196.51131661259
DarkChem[M-H]-197.50131661259
DeepCCS[M-2H]-231.78430932474
DeepCCS[M+Na]+207.08330932474
AllCCS[M+H]+201.932859911
AllCCS[M+H-H2O]+199.432859911
AllCCS[M+NH4]+204.332859911
AllCCS[M+Na]+205.032859911
AllCCS[M-H]-200.432859911
AllCCS[M+Na-2H]-201.732859911
AllCCS[M+HCOO]-203.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Apo-12'-violaxanthalC\C(C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C4354.7Standard polar33892256
Apo-12'-violaxanthalC\C(C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C3066.0Standard non polar33892256
Apo-12'-violaxanthalC\C(C=O)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C3147.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Apo-12'-violaxanthal,1TMS,isomer #1C/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)C3221.2Semi standard non polar33892256
Apo-12'-violaxanthal,1TBDMS,isomer #1C/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)C3447.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Apo-12'-violaxanthal GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-5019000000-859646253189c493ea3f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apo-12'-violaxanthal GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9723800000-ae5c58f3bf540052cb742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apo-12'-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-12'-violaxanthal 10V, Positive-QTOFsplash10-0159-1239000000-e8b8b333ae0c5b0acd972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 20V, Positive-QTOFsplash10-0292-1975000000-0f548ce3175265edf6422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 40V, Positive-QTOFsplash10-0aor-9710000000-554899cbb25bbbb2f6da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 10V, Negative-QTOFsplash10-001i-0009000000-1319620aeda5472d1bf62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 20V, Negative-QTOFsplash10-01q9-0009000000-6904a5981f74e09257922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 40V, Negative-QTOFsplash10-0pca-8965000000-301294cb2f70e9d240292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 10V, Positive-QTOFsplash10-016r-0129000000-2cf095b56f4d41d41ebe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 20V, Positive-QTOFsplash10-0159-1769000000-bdc8fec26ecee587b9472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 40V, Positive-QTOFsplash10-014i-4901000000-de9a78be90f77437144f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 10V, Negative-QTOFsplash10-0f89-0209000000-f0a239a1dd8ae4de77892021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 20V, Negative-QTOFsplash10-0udi-0109000000-984c640e5b99df56359c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apo-12'-violaxanthal 40V, Negative-QTOFsplash10-0k9b-0649000000-4842e9b6e5868a43393d2021-09-25Wishart 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 IDFDB013546
KNApSAcK IDNot Available
Chemspider ID35013802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751642
PDB IDNot Available
ChEBI ID171885
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.