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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:45:31 UTC
Update Date2022-03-07 02:54:37 UTC
HMDB IDHMDB0035742
Secondary Accession Numbers
  • HMDB35742
Metabolite Identification
Common NameAbsinthin
DescriptionAbsinthin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Absinthin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862764
Synonyms
ValueSource
(+)-AbsinthinHMDB
AbsynthinHMDB
Chemical FormulaC30H40O6
Average Molecular Weight496.635
Monoisotopic Molecular Weight496.282489012
IUPAC Name(1R,2R,5R,8S,9S,12S,13R,14S,15S,16R,17S,20S,21S,24S)-12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacosa-3,25-diene-7,22-dione
Traditional Name(1R,2R,5R,8S,9S,12S,13R,14S,15S,16R,17S,20S,21S,24S)-12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacosa-3,25-diene-7,22-dione
CAS Registry Number1362-42-1
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]3([H])C(=C(C)[C@@]4([H])[C@]3([H])[C@H]3C=C(C)[C@@]44[C@@]5([H])OC(=O)[C@@H](C)[C@]5([H])CC[C@](C)(O)[C@]34[H])[C@]1([H])OC(=O)[C@H]2C
InChI Identifier
InChI=1S/C30H40O6/c1-12-11-18-20-21(30(12)24(18)29(6,34)10-8-17-14(3)27(32)36-25(17)30)15(4)19-22(20)28(5,33)9-7-16-13(2)26(31)35-23(16)19/h11,13-14,16-18,20-25,33-34H,7-10H2,1-6H3/t13-,14-,16-,17-,18+,20-,21-,22-,23+,24-,25-,28-,29-,30+/m0/s1
InChI KeyPZHWYURJZAPXAN-NTGBWREQSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.38ALOGPS
logP2.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity133.98 m³·mol⁻¹ChemAxon
Polarizability54.99 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-235.61930932474
DeepCCS[M+Na]+209.42830932474
AllCCS[M+H]+215.532859911
AllCCS[M+H-H2O]+213.932859911
AllCCS[M+NH4]+216.932859911
AllCCS[M+Na]+217.332859911
AllCCS[M-H]-216.532859911
AllCCS[M+Na-2H]-218.132859911
AllCCS[M+HCOO]-219.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Absinthin[H][C@@]12CC[C@](C)(O)[C@@]3([H])C(=C(C)[C@@]4([H])[C@]3([H])[C@H]3C=C(C)[C@@]44[C@@]5([H])OC(=O)[C@@H](C)[C@]5([H])CC[C@](C)(O)[C@]34[H])[C@]1([H])OC(=O)[C@H]2C4544.7Standard polar33892256
Absinthin[H][C@@]12CC[C@](C)(O)[C@@]3([H])C(=C(C)[C@@]4([H])[C@]3([H])[C@H]3C=C(C)[C@@]44[C@@]5([H])OC(=O)[C@@H](C)[C@]5([H])CC[C@](C)(O)[C@]34[H])[C@]1([H])OC(=O)[C@H]2C3795.5Standard non polar33892256
Absinthin[H][C@@]12CC[C@](C)(O)[C@@]3([H])C(=C(C)[C@@]4([H])[C@]3([H])[C@H]3C=C(C)[C@@]44[C@@]5([H])OC(=O)[C@@H](C)[C@]5([H])CC[C@](C)(O)[C@]34[H])[C@]1([H])OC(=O)[C@H]2C4374.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Absinthin,1TMS,isomer #1CC1=C[C@@H]2[C@@H]3[C@@H]4C(=C(C)[C@@H]3[C@]13[C@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@](C)(O)[C@H]23)[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@]4(C)O[Si](C)(C)C3720.3Semi standard non polar33892256
Absinthin,1TMS,isomer #2CC1=C[C@@H]2[C@@H]3[C@@H]4C(=C(C)[C@@H]3[C@]13[C@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@](C)(O[Si](C)(C)C)[C@H]23)[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@]4(C)O3692.0Semi standard non polar33892256
Absinthin,2TMS,isomer #1CC1=C[C@@H]2[C@@H]3[C@@H]4C(=C(C)[C@@H]3[C@]13[C@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@](C)(O[Si](C)(C)C)[C@H]23)[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@]4(C)O[Si](C)(C)C3731.8Semi standard non polar33892256
Absinthin,1TBDMS,isomer #1CC1=C[C@@H]2[C@@H]3[C@@H]4C(=C(C)[C@@H]3[C@]13[C@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@](C)(O)[C@H]23)[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@]4(C)O[Si](C)(C)C(C)(C)C3923.9Semi standard non polar33892256
Absinthin,1TBDMS,isomer #2CC1=C[C@@H]2[C@@H]3[C@@H]4C(=C(C)[C@@H]3[C@]13[C@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]23)[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@]4(C)O3903.1Semi standard non polar33892256
Absinthin,2TBDMS,isomer #1CC1=C[C@@H]2[C@@H]3[C@@H]4C(=C(C)[C@@H]3[C@]13[C@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]23)[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC[C@]4(C)O[Si](C)(C)C(C)(C)C4157.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Absinthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fi0-0006900000-e8c767aaef1b6397d2982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Absinthin GC-MS (2 TMS) - 70eV, Positivesplash10-004j-1002094000-21f7527ebee54735b5932017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Absinthin 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 - Absinthin 10V, Positive-QTOFsplash10-004j-0000900000-2909fbf81fb602ac30402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 20V, Positive-QTOFsplash10-0a4i-0000900000-d21c9a562619077b56742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 40V, Positive-QTOFsplash10-0pdi-0113900000-fbf7600ee6a63175538b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 10V, Negative-QTOFsplash10-0f6t-0000900000-2f932edb370d1947b2622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 20V, Negative-QTOFsplash10-0fba-0000900000-e3a2c3e35015199b32762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 40V, Negative-QTOFsplash10-0a4j-1005900000-f8c6020ac55c939ae28f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 10V, Negative-QTOFsplash10-0002-0000900000-3ce13dc0a54418d1eaa72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 20V, Negative-QTOFsplash10-0002-0000900000-675e4b5de9ee622e186e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 40V, Negative-QTOFsplash10-004l-0000900000-7afc047653039e36577c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 10V, Positive-QTOFsplash10-002b-0000900000-4dfba645c32b3bfbcfd82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 20V, Positive-QTOFsplash10-004i-0000900000-61a54a50ded6571463052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Absinthin 40V, Positive-QTOFsplash10-00fr-0148900000-dabe332aee66d1b286d82021-09-24Wishart 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 IDFDB015295
KNApSAcK IDC00020965
Chemspider ID308995
KEGG Compound IDC09286
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAbsinthin
METLIN IDNot Available
PubChem Compound131751859
PDB IDNot Available
ChEBI ID2366
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. Zhang W, Luo S, Fang F, Chen Q, Hu H, Jia X, Zhai H: Total synthesis of absinthin. J Am Chem Soc. 2005 Jan 12;127(1):18-9. [PubMed:15631427 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.