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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:28 UTC
HMDB IDHMDB0015255
Secondary Accession Numbers
  • HMDB15255
Metabolite Identification
Common NameProflavine
DescriptionProflavine is only found in individuals that have used or taken this drug. It is a topical antiseptic used mainly in wound dressings. [PubChem]Proflavine acts by interchelating DNA (intercalation), thereby disrupting DNA synthesis and leading to high levels of mutation in the copied DNA strands. This prevents bacterial reproduction.
Structure
Data?1676999908
Synonyms
ValueSource
2,8-DiaminoacridineChEBI
3,6-AcridinediamineChEBI
ProflavinChEBI
ProflavinaChEBI
ProflavinumChEBI
3,6 Diamino acridineHMDB
Acridine, 3,6-diaminoHMDB
Hemisulfate, proflavineHMDB
Proflavine hemisulfateHMDB
3,6 DiaminoacridineHMDB
3,6-Diamino acridineHMDB
3,6-DiaminoacridineHMDB
ProflavineChEBI
Chemical FormulaC13H11N3
Average Molecular Weight209.2465
Monoisotopic Molecular Weight209.095297367
IUPAC Nameacridine-3,6-diamine
Traditional Nameproflavine
CAS Registry Number92-62-6
SMILES
NC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C1
InChI Identifier
InChI=1S/C13H11N3/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10/h1-7H,14-15H2
InChI KeyWDVSHHCDHLJJJR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Aminoquinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling Point410.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.1 g/LNot Available
LogP1.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.1ALOGPS
logP1.85ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.46 m³·mol⁻¹ChemAxon
Polarizability23.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+147.23731661259
DarkChem[M-H]-147.42231661259
DeepCCS[M+H]+152.93530932474
DeepCCS[M-H]-150.53930932474
DeepCCS[M-2H]-183.68530932474
DeepCCS[M+Na]+158.9530932474
AllCCS[M+H]+147.532859911
AllCCS[M+H-H2O]+143.232859911
AllCCS[M+NH4]+151.532859911
AllCCS[M+Na]+152.632859911
AllCCS[M-H]-150.432859911
AllCCS[M+Na-2H]-150.132859911
AllCCS[M+HCOO]-149.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProflavineNC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C13493.3Standard polar33892256
ProflavineNC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C12489.5Standard non polar33892256
ProflavineNC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C12870.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Proflavine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N)=CC3=NC2=C12649.3Semi standard non polar33892256
Proflavine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N)=CC3=NC2=C12569.4Standard non polar33892256
Proflavine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N)=CC3=NC2=C13388.3Standard polar33892256
Proflavine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N[Si](C)(C)C)=CC3=NC2=C12769.4Semi standard non polar33892256
Proflavine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N[Si](C)(C)C)=CC3=NC2=C12738.8Standard non polar33892256
Proflavine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N[Si](C)(C)C)=CC3=NC2=C13056.3Standard polar33892256
Proflavine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C2C=C3C=CC(N)=CC3=NC2=C1)[Si](C)(C)C2735.0Semi standard non polar33892256
Proflavine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C2C=C3C=CC(N)=CC3=NC2=C1)[Si](C)(C)C2616.6Standard non polar33892256
Proflavine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C2C=C3C=CC(N)=CC3=NC2=C1)[Si](C)(C)C3185.5Standard polar33892256
Proflavine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC3=NC2=C12709.5Semi standard non polar33892256
Proflavine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC3=NC2=C12737.8Standard non polar33892256
Proflavine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C2C=C3C=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC3=NC2=C12913.4Standard polar33892256
Proflavine,4TMS,isomer #1C[Si](C)(C)N(C1=CC2=NC3=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C3C=C2C=C1)[Si](C)(C)C2671.4Semi standard non polar33892256
Proflavine,4TMS,isomer #1C[Si](C)(C)N(C1=CC2=NC3=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C3C=C2C=C1)[Si](C)(C)C2723.0Standard non polar33892256
Proflavine,4TMS,isomer #1C[Si](C)(C)N(C1=CC2=NC3=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C3C=C2C=C1)[Si](C)(C)C2782.0Standard polar33892256
Proflavine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N)=CC3=NC2=C12903.9Semi standard non polar33892256
Proflavine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N)=CC3=NC2=C12729.0Standard non polar33892256
Proflavine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N)=CC3=NC2=C13431.2Standard polar33892256
Proflavine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N[Si](C)(C)C(C)(C)C)=CC3=NC2=C13222.8Semi standard non polar33892256
Proflavine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N[Si](C)(C)C(C)(C)C)=CC3=NC2=C13091.0Standard non polar33892256
Proflavine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N[Si](C)(C)C(C)(C)C)=CC3=NC2=C13200.3Standard polar33892256
Proflavine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C2C=C3C=CC(N)=CC3=NC2=C1)[Si](C)(C)C(C)(C)C3091.1Semi standard non polar33892256
Proflavine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C2C=C3C=CC(N)=CC3=NC2=C1)[Si](C)(C)C(C)(C)C3034.3Standard non polar33892256
Proflavine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C2C=C3C=CC(N)=CC3=NC2=C1)[Si](C)(C)C(C)(C)C3235.1Standard polar33892256
Proflavine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC3=NC2=C13338.9Semi standard non polar33892256
Proflavine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC3=NC2=C13337.7Standard non polar33892256
Proflavine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2C=C3C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC3=NC2=C13161.8Standard polar33892256
Proflavine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC2=NC3=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C3C=C2C=C1)[Si](C)(C)C(C)(C)C3532.2Semi standard non polar33892256
Proflavine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC2=NC3=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C3C=C2C=C1)[Si](C)(C)C(C)(C)C3514.0Standard non polar33892256
Proflavine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC2=NC3=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C3C=C2C=C1)[Si](C)(C)C(C)(C)C3118.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Proflavine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0690000000-03815a906da0db330dec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Proflavine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Proflavine 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 - Proflavine 10V, Negative-QTOFsplash10-0a4i-0090000000-2d2fcba70076532251192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 20V, Negative-QTOFsplash10-0a4i-0090000000-2d2fcba70076532251192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 40V, Negative-QTOFsplash10-0a4i-0690000000-8af136e71fc36f3624212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 10V, Negative-QTOFsplash10-0a4i-0090000000-fa5f60c40456eef88d832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 20V, Negative-QTOFsplash10-0a4i-0090000000-fa5f60c40456eef88d832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 40V, Negative-QTOFsplash10-0aor-0690000000-df47fd61f899d4a92e8c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 10V, Positive-QTOFsplash10-03di-0090000000-858dba584d4da0dcfd522016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 20V, Positive-QTOFsplash10-03di-0090000000-aad756b4fd7b4ae5edb82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 40V, Positive-QTOFsplash10-001i-0910000000-3ea8664c80d32002e6222016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 10V, Positive-QTOFsplash10-03di-0090000000-b9b527453679e6dc20b62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 20V, Positive-QTOFsplash10-03di-0090000000-b9b527453679e6dc20b62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proflavine 40V, Positive-QTOFsplash10-090r-0950000000-c2246d5413615c6a2a0d2021-10-11Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01123 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01123 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01123
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6832
KEGG Compound IDC11181
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProflavine
METLIN IDNot Available
PubChem Compound7099
PDB IDNot Available
ChEBI ID8452
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1098701
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available