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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:49 UTC
Update Date2022-03-07 02:53:47 UTC
HMDB IDHMDB0033600
Secondary Accession Numbers
  • HMDB33600
Metabolite Identification
Common NameSagerinic acid
DescriptionSagerinic acid, also known as sagerinate, belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms. Sagerinic acid has been detected, but not quantified in, several different foods, such as herbs and spices, green tea, teas (Camellia sinensis), black tea, and herbal tea. This could make sagerinic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sagerinic acid.
Structure
Data?1563862431
Synonyms
ValueSource
SagerinateGenerator
(+)-Sagerinic acidHMDB
2-(2-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3,4-bis(3,4-dihydroxyphenyl)cyclobutanecarbonyloxy)-3-(3,4-dihydroxyphenyl)propanoateGenerator
Chemical FormulaC36H32O16
Average Molecular Weight720.6297
Monoisotopic Molecular Weight720.169034976
IUPAC Name2-(2-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3,4-bis(3,4-dihydroxyphenyl)cyclobutanecarbonyloxy)-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Name2-(2-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3,4-bis(3,4-dihydroxyphenyl)cyclobutanecarbonyloxy)-3-(3,4-dihydroxyphenyl)propanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)C1C(C(C1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC=C(O)C(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C36H32O16/c37-19-5-1-15(9-23(19)41)11-27(33(45)46)51-35(49)31-29(17-3-7-21(39)25(43)13-17)30(18-4-8-22(40)26(44)14-18)32(31)36(50)52-28(34(47)48)12-16-2-6-20(38)24(42)10-16/h1-10,13-14,27-32,37-44H,11-12H2,(H,45,46)(H,47,48)
InChI KeySUYLTDFWHNXGDX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassCyclobutane lignans
Sub ClassNot Available
Direct ParentCyclobutane lignans
Alternative Parents
Substituents
  • Cyclobutane lignan skeleton
  • Dibenzylbutane lignan skeleton
  • Stilbene
  • Tetracarboxylic acid or derivatives
  • 3-phenylpropanoic-acid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility0.12 g/LALOGPS
logP3.91ALOGPS
logP4.33ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.81ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area289.04 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity175.95 m³·mol⁻¹ChemAxon
Polarizability67.42 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+259.27831661259
DarkChem[M-H]-248.12131661259
DeepCCS[M+H]+252.7430932474
DeepCCS[M-H]-250.84530932474
DeepCCS[M-2H]-284.65430932474
DeepCCS[M+Na]+258.56830932474
AllCCS[M+H]+253.732859911
AllCCS[M+H-H2O]+253.232859911
AllCCS[M+NH4]+254.132859911
AllCCS[M+Na]+254.332859911
AllCCS[M-H]-247.432859911
AllCCS[M+Na-2H]-250.132859911
AllCCS[M+HCOO]-253.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sagerinic acidOC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)C1C(C(C1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC=C(O)C(O)=C1)C(O)=O9355.2Standard polar33892256
Sagerinic acidOC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)C1C(C(C1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC=C(O)C(O)=C1)C(O)=O4882.3Standard non polar33892256
Sagerinic acidOC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)C1C(C(C1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC=C(O)C(O)=C1)C(O)=O6580.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-1921520000-d96a4aca6c241e953a062017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_18) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_19) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sagerinic acid , negative-QTOFsplash10-03di-0902000000-1a1faddf80089d58bfe82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sagerinic acid , positive-QTOFsplash10-03di-0900000000-bb8ee6e45c31480087a62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 10V, Positive-QTOFsplash10-00di-0900041800-d8de10ee4e2aa08890f52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 20V, Positive-QTOFsplash10-00e9-0900122200-0106e5e32e7922dc081a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 40V, Positive-QTOFsplash10-00rb-0953101000-2db845aeb3f2c82454752016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 10V, Negative-QTOFsplash10-016r-0810261900-a79cd72c8538561fe8732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 20V, Negative-QTOFsplash10-002r-0903452100-8b58476e06783bba06d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 40V, Negative-QTOFsplash10-0a4i-0309410000-8447f34ee8e58a1b0e6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 10V, Negative-QTOFsplash10-00os-0100938300-7f97188d37f68411f7012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 20V, Negative-QTOFsplash10-00n1-0700689200-ebb7b001701a40c7bff62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 40V, Negative-QTOFsplash10-000e-0500839100-eb409f0d85ca4bfbf8b82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 10V, Positive-QTOFsplash10-0w90-0213546900-4a9855a0bb05002942c02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 20V, Positive-QTOFsplash10-000i-0319770000-2b0d4d4fdcfd32431da72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sagerinic acid 40V, Positive-QTOFsplash10-0a4i-1902203000-7af6d10f702a823fe3652021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB011686
KNApSAcK IDC00037767
Chemspider ID23551155
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23760102
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .