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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:22:10 UTC
Update Date2022-03-07 02:56:02 UTC
HMDB IDHMDB0039017
Secondary Accession Numbers
  • HMDB39017
Metabolite Identification
Common NameSemi-beta-carotenone
DescriptionSemi-beta-carotenone belongs to the class of organic compounds known as sesquaterpenoids. These are terpenoids with at least 7 consecutive isoprene units. Based on a literature review a small amount of articles have been published on Semi-beta-carotenone.
Structure
Data?1563863297
Synonyms
ValueSource
Semi-b-carotenoneGenerator
Semi-β-carotenoneGenerator
Chemical FormulaC40H56O2
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
IUPAC Name(8E,10E,12E,14E,16E,18E,20Z,22Z,24E)-6,6,10,14,19,23-hexamethyl-25-(2,6,6-trimethylcyclohex-1-en-1-yl)pentacosa-8,10,12,14,16,18,20,22,24-nonaene-2,7-dione
Traditional Name(8E,10E,12E,14E,16E,18E,20Z,22Z,24E)-6,6,10,14,19,23-hexamethyl-25-(2,6,6-trimethylcyclohex-1-en-1-yl)pentacosa-8,10,12,14,16,18,20,22,24-nonaene-2,7-dione
CAS Registry Number20126-73-2
SMILES
CC(=O)CCCC(C)(C)C(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C40H56O2/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38(42)40(9,10)30-16-24-36(6)41/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13-,20-14+,27-25+,28-26+,31-17+,32-18+,33-21-,34-22+
InChI KeyPDBIWYOLPQXSTF-LXAKRSFRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquaterpenoids. These are terpenoids with at least 7 consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquaterpenoids
Direct ParentSesquaterpenoids
Alternative Parents
Substituents
  • Sesquaterpenoid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point118 - 119 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.7e-10 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00041 g/LALOGPS
logP9.14ALOGPS
logP10.61ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity194.22 m³·mol⁻¹ChemAxon
Polarizability73.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+256.17430932474
DeepCCS[M-H]-254.34930932474
DeepCCS[M-2H]-287.59130932474
DeepCCS[M+Na]+261.7830932474
AllCCS[M+H]+256.732859911
AllCCS[M+H-H2O]+255.132859911
AllCCS[M+NH4]+258.232859911
AllCCS[M+Na]+258.632859911
AllCCS[M-H]-229.632859911
AllCCS[M+Na-2H]-234.032859911
AllCCS[M+HCOO]-239.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Semi-beta-carotenoneCC(=O)CCCC(C)(C)C(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C5630.0Standard polar33892256
Semi-beta-carotenoneCC(=O)CCCC(C)(C)C(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C4666.2Standard non polar33892256
Semi-beta-carotenoneCC(=O)CCCC(C)(C)C(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C4383.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Semi-beta-carotenone,1TMS,isomer #1CC(=CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C4715.4Semi standard non polar33892256
Semi-beta-carotenone,1TMS,isomer #1CC(=CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C4587.1Standard non polar33892256
Semi-beta-carotenone,1TMS,isomer #2C=C(CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C4670.6Semi standard non polar33892256
Semi-beta-carotenone,1TMS,isomer #2C=C(CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C4503.3Standard non polar33892256
Semi-beta-carotenone,1TBDMS,isomer #1CC(=CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C4919.7Semi standard non polar33892256
Semi-beta-carotenone,1TBDMS,isomer #1CC(=CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C4810.2Standard non polar33892256
Semi-beta-carotenone,1TBDMS,isomer #2C=C(CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C4865.9Semi standard non polar33892256
Semi-beta-carotenone,1TBDMS,isomer #2C=C(CCCC(C)(C)C(=O)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C\C=C(C)/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C4710.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Semi-beta-carotenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-6100490000-c7c72f4bbdcfc19ed8a52017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 10V, Positive-QTOFsplash10-0uxr-0212290000-617ea944194c145b6eae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 20V, Positive-QTOFsplash10-03ds-1749730000-cb6a0de7c896dba598692016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 40V, Positive-QTOFsplash10-0hkj-5937610000-95d00a2f54607f98efbf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 10V, Negative-QTOFsplash10-014i-0100090000-5dd1fc290746b9df1c5d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 20V, Negative-QTOFsplash10-014i-2300490000-961b8a11fd02d9983c3c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 40V, Negative-QTOFsplash10-0pvr-9302740000-af77bf23070ab27355a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 10V, Negative-QTOFsplash10-014i-0000190000-ac6ad7a8dd6003b266fc2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 20V, Negative-QTOFsplash10-066r-3512290000-0e3215a79293b4d3f29a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 40V, Negative-QTOFsplash10-0bt9-8405930000-5ed0b7d07e91cf082f352021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 10V, Positive-QTOFsplash10-0frt-0105290000-1a89d36ca594d5fc72092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 20V, Positive-QTOFsplash10-0il9-3305910000-bc048fa85c5e60798dd72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Semi-beta-carotenone 40V, Positive-QTOFsplash10-02ai-6626900000-c1798de43389fa3a9af52021-09-25Wishart 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 IDFDB018512
KNApSAcK IDC00023168
Chemspider ID30777313
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752514
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1873551
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.