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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 16:54:39 UTC
Update Date2021-10-01 22:50:14 UTC
HMDB IDHMDB0256449
Secondary Accession NumbersNone
Metabolite Identification
Common NamePheophorbide a
DescriptionBased on a literature review very few articles have been published on 3-[16-ethenyl-11-ethyl-4-hydroxy-3-(methoxycarbonyl)-12,17,21,26-tetramethyl-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pheophorbide a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pheophorbide a is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
3-[16-Ethenyl-11-ethyl-4-hydroxy-3-(methoxycarbonyl)-12,17,21,26-tetramethyl-7,23,24,25-tetraazahexacyclo[18.2.1.1,.1,.1,.0,]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoateGenerator
Chemical FormulaC35H36N4O5
Average Molecular Weight592.696
Monoisotopic Molecular Weight592.268570275
IUPAC Name3-[16-ethenyl-11-ethyl-4-hydroxy-3-(methoxycarbonyl)-12,17,21,26-tetramethyl-7,23,24,25-tetraazahexacyclo[18.2.1.1^{5,8}.1^{10,13}.1^{15,18}.0^{2,6}]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid
Traditional Name3-[16-ethenyl-11-ethyl-4-hydroxy-3-(methoxycarbonyl)-12,17,21,26-tetramethyl-7,23,24,25-tetraazahexacyclo[18.2.1.1^{5,8}.1^{10,13}.1^{15,18}.0^{2,6}]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
CCC1=C(C)C2=NC1=CC1=C(C)C3=C(O)C(C(=O)OC)\C(=C4\NC(=CC5=NC(=C2)C(C=C)=C5C)C(C)C4CCC(O)=O)C3=N1
InChI Identifier
InChI=1S/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,38,42H,1,9-11H2,2-7H3,(H,40,41)/b24-12?,26-13?,27-14?,32-30-
InChI KeyRKEBXTALJSALNU-BHQAOJCSSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(4.45) g/LALOGPS
logP10(-1.5) g/LChemAxon
logS10(-4.2) g/LALOGPS
pKa (Strongest Acidic)-6.1ChemAxon
pKa (Strongest Basic)15.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area132.94 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity177.19 m³·mol⁻¹ChemAxon
Polarizability68.38 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pheophorbide aCCC1=C(C)C2=NC1=CC1=C(C)C3=C(O)C(C(=O)OC)\C(=C4\NC(=CC5=NC(=C2)C(C=C)=C5C)C(C)C4CCC(O)=O)C3=N17172.8Standard polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Pheophorbide aCCC1=C(C)C2=NC1=CC1=C(C)C3=C(O)C(C(=O)OC)\C(=C4\NC(=CC5=NC(=C2)C(C=C)=C5C)C(C)C4CCC(O)=O)C3=N14312.0Standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Pheophorbide aCCC1=C(C)C2=NC1=CC1=C(C)C3=C(O)C(C(=O)OC)\C(=C4\NC(=CC5=NC(=C2)C(C=C)=C5C)C(C)C4CCC(O)=O)C3=N15425.5Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
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 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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Binds heme and porphyrins and functions in their ATP- dependent uptake into the mitochondria. Plays a crucial role in heme synthesis
Gene Name:
ABCB6
Uniprot ID:
Q9NP58
Molecular weight:
93884.7
General function:
Not Available
Specific function:
Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:10485464, PubMed:12477054, PubMed:12429862, PubMed:17145775, PubMed:30042379). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:12429862, PubMed:15044468). Also mediates the efflux of sphingosine-1-P from cells (By similarity). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (By similarity). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (PubMed:30042379). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (By similarity). Mediates the secretion of the riboflavin and biotin vitamins into milk (PubMed:17145775). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (PubMed:12429862). Plays an important role in the exclusion of xenobiotics from the brain (PubMed:10485464). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:12477054). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (PubMed:12429862). May play a role in early stem cell self-renewal by blocking differentiation (Probable).
Gene Name:
ABCG2
Uniprot ID:
Q7TMS5
Molecular weight:
72977.13

Transporters

General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5