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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:18 UTC
Update Date2022-03-07 02:52:50 UTC
HMDB IDHMDB0031149
Secondary Accession Numbers
  • HMDB31149
Metabolite Identification
Common NamePhaeophorbide b
DescriptionPhaeophorbide b belongs to the class of organic compounds known as chlorins. These are large heterocyclic aromatic ring systems consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages. Phaeophorbide b is a very strong basic compound (based on its pKa). Outside of the human body, phaeophorbide b has been detected, but not quantified in, brassicas. This could make phaeophorbide b a potential biomarker for the consumption of these foods.
Structure
Data?1563862088
Synonyms
ValueSource
Phaeophorbid bHMDB
Phaeophorbid-bHMDB
Pheophorbide bHMDB
3-[16-Ethenyl-11-ethyl-12-formyl-3-(methoxycarbonyl)-17,21,26-trimethyl-4-oxo-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,5,8(26),9,11,13(25),14,16,18,20(23)-decaen-22-yl]propanoateGenerator
Chemical FormulaC35H34N4O6
Average Molecular Weight606.6677
Monoisotopic Molecular Weight606.24783484
IUPAC Name3-[16-ethenyl-11-ethyl-12-formyl-3-(methoxycarbonyl)-17,21,26-trimethyl-4-oxo-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,5,8(26),9,11,13(25),14,16,18,20(23)-decaen-22-yl]propanoic acid
Traditional Name3-[16-ethenyl-11-ethyl-12-formyl-3-(methoxycarbonyl)-17,21,26-trimethyl-4-oxo-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,5,8(26),9,11,13(25),14,16,18,20(23)-decaen-22-yl]propanoic acid
CAS Registry Number20239-99-0
SMILES
CCC1=C(C=O)C2=N\C\1=C/C1=C(C)C3=C(N1)\C(C(C(=O)OC)C3=O)=C1/N=C(/C=C3\N/C(=C\2)C(C=C)=C3C)C(C)C1CCC(O)=O
InChI Identifier
InChI=1S/C35H34N4O6/c1-7-18-15(3)22-11-23-16(4)20(9-10-28(41)42)32(38-23)30-31(35(44)45-6)34(43)29-17(5)24(39-33(29)30)12-26-19(8-2)21(14-40)27(37-26)13-25(18)36-22/h7,11-14,16,20,31,36,39H,1,8-10H2,2-6H3,(H,41,42)/b22-11-,23-11-,24-12-,25-13-,26-12-,27-13-,32-30-
InChI KeyPROPHBCDMQAJMH-DZJPEQLASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorins. These are large heterocyclic aromatic ring systems consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassChlorins
Direct ParentChlorins
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point220 - 223 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.66ALOGPS
logP4.12ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)6.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area155.1 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.01 m³·mol⁻¹ChemAxon
Polarizability68.05 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+250.53630932474
DeepCCS[M-H]-248.6430932474
DeepCCS[M-2H]-281.92330932474
DeepCCS[M+Na]+256.18630932474
AllCCS[M+H]+243.232859911
AllCCS[M+H-H2O]+241.832859911
AllCCS[M+NH4]+244.432859911
AllCCS[M+Na]+244.832859911
AllCCS[M-H]-240.832859911
AllCCS[M+Na-2H]-242.932859911
AllCCS[M+HCOO]-245.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phaeophorbide bCCC1=C(C=O)C2=N\C\1=C/C1=C(C)C3=C(N1)\C(C(C(=O)OC)C3=O)=C1/N=C(/C=C3\N/C(=C\2)C(C=C)=C3C)C(C)C1CCC(O)=O5829.2Standard polar33892256
Phaeophorbide bCCC1=C(C=O)C2=N\C\1=C/C1=C(C)C3=C(N1)\C(C(C(=O)OC)C3=O)=C1/N=C(/C=C3\N/C(=C\2)C(C=C)=C3C)C(C)C1CCC(O)=O3909.1Standard non polar33892256
Phaeophorbide bCCC1=C(C=O)C2=N\C\1=C/C1=C(C)C3=C(N1)\C(C(C(=O)OC)C3=O)=C1/N=C(/C=C3\N/C(=C\2)C(C=C)=C3C)C(C)C1CCC(O)=O5834.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phaeophorbide b,1TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)[NH]5)C(CCC(=O)O[Si](C)(C)C)C3C5425.5Semi standard non polar33892256
Phaeophorbide b,1TMS,isomer #2C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O)C3C5488.9Semi standard non polar33892256
Phaeophorbide b,1TMS,isomer #3C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)[NH]5)C(CCC(=O)O)C3C5518.4Semi standard non polar33892256
Phaeophorbide b,2TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)C3C5318.1Semi standard non polar33892256
Phaeophorbide b,2TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)C3C4529.9Standard non polar33892256
Phaeophorbide b,2TMS,isomer #2C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)[NH]5)C(CCC(=O)O[Si](C)(C)C)C3C5353.4Semi standard non polar33892256
Phaeophorbide b,2TMS,isomer #2C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)[NH]5)C(CCC(=O)O[Si](C)(C)C)C3C4594.7Standard non polar33892256
Phaeophorbide b,2TMS,isomer #3C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O)C3C5428.3Semi standard non polar33892256
Phaeophorbide b,2TMS,isomer #3C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O)C3C4568.6Standard non polar33892256
Phaeophorbide b,3TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)C3C5279.7Semi standard non polar33892256
Phaeophorbide b,3TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C)C(C=O)=C4CC)N5[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)C3C4549.6Standard non polar33892256
Phaeophorbide b,1TBDMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)[NH]5)C(CCC(=O)O[Si](C)(C)C(C)(C)C)C3C5627.9Semi standard non polar33892256
Phaeophorbide b,1TBDMS,isomer #2C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)C3C5636.8Semi standard non polar33892256
Phaeophorbide b,1TBDMS,isomer #3C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C(C)(C)C)C(C=O)=C4CC)[NH]5)C(CCC(=O)O)C3C5660.0Semi standard non polar33892256
Phaeophorbide b,2TBDMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)C3C5664.9Semi standard non polar33892256
Phaeophorbide b,2TBDMS,isomer #1C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1[NH]2)C(C=O)=C4CC)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)C3C4865.4Standard non polar33892256
Phaeophorbide b,2TBDMS,isomer #2C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C(C)(C)C)C(C=O)=C4CC)[NH]5)C(CCC(=O)O[Si](C)(C)C(C)(C)C)C3C5674.2Semi standard non polar33892256
Phaeophorbide b,2TBDMS,isomer #2C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C(C)(C)C)C(C=O)=C4CC)[NH]5)C(CCC(=O)O[Si](C)(C)C(C)(C)C)C3C4930.9Standard non polar33892256
Phaeophorbide b,2TBDMS,isomer #3C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C(C)(C)C)C(C=O)=C4CC)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)C3C5731.5Semi standard non polar33892256
Phaeophorbide b,2TBDMS,isomer #3C=CC1=C(C)C2=CC3=NC(=C4C5=C(C(=O)C4C(=O)OC)C(C)=C(C=C4N=C(C=C1N2[Si](C)(C)C(C)(C)C)C(C=O)=C4CC)N5[Si](C)(C)C(C)(C)C)C(CCC(=O)O)C3C4891.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-3000090000-4696a8d53f671e406b812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (1 TMS) - 70eV, Positivesplash10-03dr-9000077000-b5f7fb54e7549b7c60702017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaeophorbide b GC-MS ("Phaeophorbide b,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 10V, Positive-QTOFsplash10-000i-0000091000-ad4c9eb1d9f55351a4ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 20V, Positive-QTOFsplash10-06tr-0000090000-7c4e11d874992c1b2aba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 40V, Positive-QTOFsplash10-0f79-1000980000-023f9eda9ce5d7c7af0e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 10V, Negative-QTOFsplash10-0a4i-0000089000-2abd7858c138154838cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 20V, Negative-QTOFsplash10-0a6r-0000091000-a454c3d1d9baadd567992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 40V, Negative-QTOFsplash10-0aor-4000090000-40e1339bf31b282ea8ed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 10V, Positive-QTOFsplash10-0a4i-0000098000-f03665ebbef448cbc2222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 20V, Positive-QTOFsplash10-0a71-0000092000-102fb5a28e13a4487bda2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 40V, Positive-QTOFsplash10-014i-0000190000-aa31af6113f03c13aa152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 10V, Negative-QTOFsplash10-0a4i-0000097000-d323b1852aedc0b74a4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 20V, Negative-QTOFsplash10-0a59-0000090000-6207d407bcc5af75f1b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaeophorbide b 40V, Negative-QTOFsplash10-0kai-0000190000-65b27c7ea81257bdf9712021-09-22Wishart 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 IDFDB003161
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID38258
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.. .