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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:11:54 UTC
Update Date2022-03-07 02:56:40 UTC
HMDB IDHMDB0040635
Secondary Accession Numbers
  • HMDB40635
Metabolite Identification
Common NamePiperochromenoic acid
DescriptionPiperochromenoic acid, also known as piperochromenoate, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a small amount of articles have been published on Piperochromenoic acid.
Structure
Data?1563863571
Synonyms
ValueSource
PiperochromenoateGenerator
2-(4,8-Dimethyl-3,7-nonadienyl)-2-methyl-2H-1-benzopyran-6-carboxylic acid, 9ciHMDB
2-[(3E)-4,8-Dimethylnona-3,7-dien-1-yl]-2-methyl-2H-chromene-6-carboxylateGenerator
Chemical FormulaC22H28O3
Average Molecular Weight340.4559
Monoisotopic Molecular Weight340.203844762
IUPAC Name2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-2H-chromene-6-carboxylic acid
Traditional Name2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methylchromene-6-carboxylic acid
CAS Registry Number110979-01-6
SMILES
CC(C)=CCC\C(C)=C\CCC1(C)OC2=CC=C(C=C2C=C1)C(O)=O
InChI Identifier
InChI=1S/C22H28O3/c1-16(2)7-5-8-17(3)9-6-13-22(4)14-12-18-15-19(21(23)24)10-11-20(18)25-22/h7,9-12,14-15H,5-6,8,13H2,1-4H3,(H,23,24)/b17-9+
InChI KeyMSDAWPKHHPLFBC-RQZCQDPDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Benzopyran
  • Bicyclic monoterpenoid
  • 1-benzopyran
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.0008 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP6.27ALOGPS
logP5.93ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.24 m³·mol⁻¹ChemAxon
Polarizability39.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.17831661259
DarkChem[M-H]-183.12631661259
DeepCCS[M+H]+184.74730932474
DeepCCS[M-H]-182.38130932474
DeepCCS[M-2H]-215.94930932474
DeepCCS[M+Na]+191.58730932474
AllCCS[M+H]+189.232859911
AllCCS[M+H-H2O]+186.232859911
AllCCS[M+NH4]+192.032859911
AllCCS[M+Na]+192.832859911
AllCCS[M-H]-187.132859911
AllCCS[M+Na-2H]-187.432859911
AllCCS[M+HCOO]-188.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Piperochromenoic acidCC(C)=CCC\C(C)=C\CCC1(C)OC2=CC=C(C=C2C=C1)C(O)=O3769.9Standard polar33892256
Piperochromenoic acidCC(C)=CCC\C(C)=C\CCC1(C)OC2=CC=C(C=C2C=C1)C(O)=O2590.4Standard non polar33892256
Piperochromenoic acidCC(C)=CCC\C(C)=C\CCC1(C)OC2=CC=C(C=C2C=C1)C(O)=O2700.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Piperochromenoic acid,1TMS,isomer #1CC(C)=CCC/C(C)=C/CCC1(C)C=CC2=CC(C(=O)O[Si](C)(C)C)=CC=C2O12681.6Semi standard non polar33892256
Piperochromenoic acid,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CCC1(C)C=CC2=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C2O12950.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Piperochromenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-5924000000-f1813348228a5dc931b12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piperochromenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-02ft-7659000000-af62c1491bb30b44c4642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piperochromenoic acid 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 - Piperochromenoic acid 10V, Positive-QTOFsplash10-006y-0449000000-a9357e4604a23c5e6b1e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 20V, Positive-QTOFsplash10-0pis-2911000000-1477a98b8b68ee1146a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 40V, Positive-QTOFsplash10-0aor-8920000000-241ad46f7a38884be4c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 10V, Negative-QTOFsplash10-000i-0039000000-cfc8a48f55d09a7a14482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 20V, Negative-QTOFsplash10-000b-0297000000-6e6e6acf0f535f322cf62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 40V, Negative-QTOFsplash10-00n3-2972000000-7a93953dd8388f0ba9052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 10V, Negative-QTOFsplash10-000i-0009000000-0b542547fa4ff7747c312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 20V, Negative-QTOFsplash10-000i-0329000000-39536949665b73f6f34b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 40V, Negative-QTOFsplash10-00n1-1932000000-693c43f9094464d5f78b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 10V, Positive-QTOFsplash10-052f-1194000000-9ec05ce5c76206a43af22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 20V, Positive-QTOFsplash10-0f9t-6390000000-0d7014b40032459841302021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperochromenoic acid 40V, Positive-QTOFsplash10-05rc-5900000000-ea62a4075c503bb301e32021-09-25Wishart 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 IDFDB020426
KNApSAcK IDC00056454
Chemspider ID35014987
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13845938
PDB IDNot Available
ChEBI ID174592
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1884941
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.