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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014603
Secondary Accession Numbers
  • HMDB14603
Metabolite Identification
Common NameVerteporfin
DescriptionVerteporfin, otherwise known as benzoporphyrin derivative (trade name Visudyne), is a medication used as a photosensitizer for photodynamic therapy to eliminate the abnormal blood vessels in the eye associated with conditions such as the wet form of macular degeneration. Verteporfin accumulates in these abnormal blood vessels and, when stimulated by nonthermal red light with a wavelength of 693 nm in the presence of oxygen, produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to the endothelium and blockage of the vessels.
Structure
Data?1582753198
Synonyms
ValueSource
3-[(23S,24R)-14-Ethenyl-5-(3-methoxy-3-oxopropyl)-22,23-bis(methoxycarbonyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahexacyclo[16.6.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶.0¹⁹,²⁴]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoateHMDB
Chemical FormulaC41H42N4O8
Average Molecular Weight718.7942
Monoisotopic Molecular Weight718.30026434
IUPAC Name3-[(23S,24R)-14-ethenyl-5-(3-methoxy-3-oxopropyl)-22,23-bis(methoxycarbonyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahexacyclo[16.6.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶.0¹⁹,²⁴]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid
Traditional NameVERT
CAS Registry Number129497-78-5
SMILES
COC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C2=CC=C([C@@H](C(=O)OC)[C@@]32C)C(=O)OC)=C1C
InChI Identifier
InChI=1S/C41H42N4O8/c1-9-23-20(2)29-17-34-27-13-10-26(39(49)52-7)38(40(50)53-8)41(27,5)35(45-34)19-30-22(4)25(12-15-37(48)51-6)33(44-30)18-32-24(11-14-36(46)47)21(3)28(43-32)16-31(23)42-29/h9-10,13,16-19,38,42,44H,1,11-12,14-15H2,2-8H3,(H,46,47)/b28-16-,29-17-,30-19-,31-16-,32-18-,33-18-,34-17-,35-19-/t38-,41+/m0/s1
InChI KeyYTZALCGQUPRCGW-MXVXOLGGSA-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 FrameworkNot Available
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP2.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP5.02ALOGPS
logP6.34ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)4.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.56 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity199.08 m³·mol⁻¹ChemAxon
Polarizability81.29 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
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-2H]-290.41930932474
DeepCCS[M+Na]+264.86330932474
AllCCS[M+H]+262.532859911
AllCCS[M+H-H2O]+261.532859911
AllCCS[M+NH4]+263.332859911
AllCCS[M+Na]+263.532859911
AllCCS[M-H]-260.932859911
AllCCS[M+Na-2H]-264.332859911
AllCCS[M+HCOO]-268.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VerteporfinCOC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C2=CC=C([C@@H](C(=O)OC)[C@@]32C)C(=O)OC)=C1C6867.9Standard polar33892256
VerteporfinCOC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C2=CC=C([C@@H](C(=O)OC)[C@@]32C)C(=O)OC)=C1C4811.6Standard non polar33892256
VerteporfinCOC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C2=CC=C([C@@H](C(=O)OC)[C@@]32C)C(=O)OC)=C1C6246.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Verteporfin,2TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1[NH]2)C(C)=C5CCC(=O)O[Si](C)(C)C)N4[Si](C)(C)C)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC5896.2Semi standard non polar33892256
Verteporfin,2TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1[NH]2)C(C)=C5CCC(=O)O[Si](C)(C)C)N4[Si](C)(C)C)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC4850.7Standard non polar33892256
Verteporfin,2TMS,isomer #1C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1[NH]2)C(C)=C5CCC(=O)O[Si](C)(C)C)N4[Si](C)(C)C)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC7410.1Standard polar33892256
Verteporfin,2TMS,isomer #2C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1N2[Si](C)(C)C)C(C)=C5CCC(=O)O[Si](C)(C)C)[NH]4)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC5924.3Semi standard non polar33892256
Verteporfin,2TMS,isomer #2C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1N2[Si](C)(C)C)C(C)=C5CCC(=O)O[Si](C)(C)C)[NH]4)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC4835.8Standard non polar33892256
Verteporfin,2TMS,isomer #2C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1N2[Si](C)(C)C)C(C)=C5CCC(=O)O[Si](C)(C)C)[NH]4)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC7326.4Standard polar33892256
Verteporfin,2TMS,isomer #3C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1N2[Si](C)(C)C)C(C)=C5CCC(=O)O)N4[Si](C)(C)C)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC5998.0Semi standard non polar33892256
Verteporfin,2TMS,isomer #3C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1N2[Si](C)(C)C)C(C)=C5CCC(=O)O)N4[Si](C)(C)C)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC4849.2Standard non polar33892256
Verteporfin,2TMS,isomer #3C=CC1=C(C)C2=CC3=NC(=CC4=C(C)C(CCC(=O)OC)=C(C=C5N=C(C=C1N2[Si](C)(C)C)C(C)=C5CCC(=O)O)N4[Si](C)(C)C)[C@@]1(C)C3=CC=C(C(=O)OC)[C@H]1C(=O)OC7290.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Verteporfin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verteporfin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verteporfin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verteporfin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verteporfin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verteporfin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 10V, Negative-QTOFsplash10-014r-0000009600-89a0501bc164118f18672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 20V, Negative-QTOFsplash10-0aor-1000009100-26eeadf6aaa77d9038592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 40V, Negative-QTOFsplash10-056u-4000009000-eff443ca0bb459d0673d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 10V, Negative-QTOFsplash10-00p0-0000009200-0cb74b4edd542c40054f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 20V, Negative-QTOFsplash10-00mo-0000009100-b6fc818410d9eab222c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 40V, Negative-QTOFsplash10-03xr-0000029100-6af80c39f2d17512bce72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 10V, Positive-QTOFsplash10-0uy0-0000009400-1d7c8f1fc2dc50cfe52f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 20V, Positive-QTOFsplash10-0m0m-0000029100-7684d9a7f67a3f18d6702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 40V, Positive-QTOFsplash10-0002-1000095000-628656af2025a7bd099e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 10V, Positive-QTOFsplash10-0fr6-0000009400-844d3115b3be7e5767a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 20V, Positive-QTOFsplash10-0597-0000029100-48abe90a5dc5b255b75a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Verteporfin 40V, Positive-QTOFsplash10-03xs-1000059200-cf96237b152a02e2917c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00460 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00460 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00460
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4515032
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVerteporfin
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. Nowak-Sliwinska P, Karocki A, Elas M, Pawlak A, Stochel G, Urbanska K: Verteporfin, photofrin II, and merocyanine 540 as PDT photosensitizers against melanoma cells. Biochem Biophys Res Commun. 2006 Oct 20;349(2):549-55. Epub 2006 Aug 22. [PubMed:16945338 ]
  2. Chan WM, Lim TH, Pece A, Silva R, Yoshimura N: Verteporfin PDT for non-standard indications--a review of current literature. Graefes Arch Clin Exp Ophthalmol. 2010 May;248(5):613-26. doi: 10.1007/s00417-010-1307-z. Epub 2010 Feb 17. [PubMed:20162298 ]