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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:54 UTC
HMDB IDHMDB0015245
Secondary Accession Numbers
  • HMDB15245
Metabolite Identification
Common NamePapaverine
DescriptionPapaverine is an alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels. [PubChem].
Structure
Data?1582753274
Synonyms
ValueSource
MesotinaKegg
Chlorhydrate de papaverineHMDB
Papavarine chlorhydrateHMDB
PapaverinHMDB
Papaverine chlorohydrateHMDB
Papaverine monohydrochlorideHMDB
Papaverinium chlorideHMDB
CerespanMeSH, HMDB
Hydrochloride, papaverineMeSH, HMDB
PavatymMeSH, HMDB
PavabidMeSH, HMDB
Papaverine hydrochlorideMeSH, HMDB
Chemical FormulaC20H21NO4
Average Molecular Weight339.385
Monoisotopic Molecular Weight339.147058165
IUPAC Name1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
Traditional Namepapaverine
CAS Registry Number61-25-6
SMILES
COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
InChI Identifier
InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3
InChI KeyXQYZDYMELSJDRZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Ether
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM185.330932474
[M+H]+Not Available185.843http://allccs.zhulab.cn/database/detail?ID=AllCCS00000948
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.19ALOGPS
logP3.08ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)6.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.81 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.52 m³·mol⁻¹ChemAxon
Polarizability36.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.14731661259
DarkChem[M-H]-185.84831661259
DeepCCS[M-2H]-218.62730932474
DeepCCS[M+Na]+194.78130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PapaverineCOC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C13773.9Standard polar33892256
PapaverineCOC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C12878.8Standard non polar33892256
PapaverineCOC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C12790.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Papaverine EI-B (Non-derivatized)splash10-0079-4569000000-42d74df972bf1280fb292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Papaverine EI-B (Non-derivatized)splash10-0079-4569000000-42d74df972bf1280fb292018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Papaverine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fs-0279000000-6a8c8886127d693c85672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Papaverine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine LC-ESI-QTOF , positive-QTOFsplash10-0006-0009000000-376bdab66f9ada8143f22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine LC-ESI-QTOF , positive-QTOFsplash10-0f6x-0049000000-fbf8945b1b40a8e629ff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine LC-ESI-QTOF , positive-QTOFsplash10-00di-0779000000-37837168aff5cb2db6db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine , positive-QTOFsplash10-0006-0019000000-175d5d7601656bade9be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine , positive-QTOFsplash10-00dl-0569000000-1f7e7c97dcea64bf274a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 10V, Positive-QTOFsplash10-0006-0029000000-453bc4f2053e78c8ce452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 6V, Positive-QTOFsplash10-0ac0-0941000000-5b8b44adc1288a93aee52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 50V, Positive-QTOFsplash10-0ac0-0951000000-bb231dbbbd59dcf69c8f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 6V, Positive-QTOFsplash10-0006-0029000000-8bc67120d4b4d28737dc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 6V, Positive-QTOFsplash10-0fk9-0279000000-6ce87da6708962b5e9392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 30V, Positive-QTOFsplash10-0fk9-0279000000-c73bc5d2d851aa9cafe72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 10V, Positive-QTOFsplash10-0006-0009000000-f4615816604a967ae7862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 50V, Positive-QTOFsplash10-0ab9-0951000000-c9eb047b22f9537966202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 20V, Positive-QTOFsplash10-0f6x-0049000000-fbf8945b1b40a8e629ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 10V, Positive-QTOFsplash10-0006-0009000000-a69cf627410b83b67bd32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 40V, Positive-QTOFsplash10-00di-0779000000-37837168aff5cb2db6db2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 35V, Positive-QTOFsplash10-0fdo-0249000000-cee8c55509567c9c6d6c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 10V, Positive-QTOFsplash10-0006-0029000000-70b62b3d039f4e99bf222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Papaverine 30V, Positive-QTOFsplash10-0fk9-0379000000-7a3c6f8ee88d8001e5be2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Papaverine 10V, Positive-QTOFsplash10-0006-0009000000-5adf8eed4c99ef024ca82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Papaverine 20V, Positive-QTOFsplash10-0006-0009000000-90f688022df6ca82e68d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Papaverine 40V, Positive-QTOFsplash10-0f6x-0092000000-d2012c62f8a18f28d8e02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Papaverine 10V, Negative-QTOFsplash10-000i-0009000000-14a648b12b81f2d898df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Papaverine 20V, Negative-QTOFsplash10-000i-0019000000-3f207d6944b0d0c476ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Papaverine 40V, Negative-QTOFsplash10-0gbc-0090000000-218cfc775f1db8beaf692016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01113 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01113 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01113
Phenol Explorer Compound IDNot Available
FooDB IDFDB000447
KNApSAcK IDC00001899
Chemspider ID4518
KEGG Compound IDC06533
BioCyc IDCPD-15742
BiGG IDNot Available
Wikipedia LinkPapaverine
METLIN IDNot Available
PubChem Compound4680
PDB IDNot Available
ChEBI ID28241
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. Tang Y, Luan J, Zhang X: Accelerating tissue expansion by application of topical papaverine cream. Plast Reconstr Surg. 2004 Oct;114(5):1166-9. [PubMed:15457029 ]
  2. Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J: Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting. Eur J Cardiothorac Surg. 2004 Nov;26(5):956-9. [PubMed:15519189 ]
  3. Liu JK, Couldwell WT: Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. Neurocrit Care. 2005;2(2):124-32. [PubMed:16159054 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
Gene Name:
PDE10A
Uniprot ID:
Q9Y233
Molecular weight:
89388.7
References
  1. Weber M, Breier M, Ko D, Thangaraj N, Marzan DE, Swerdlow NR: Evaluating the antipsychotic profile of the preferential PDE10A inhibitor, papaverine. Psychopharmacology (Berl). 2009 May;203(4):723-35. doi: 10.1007/s00213-008-1419-x. Epub 2008 Dec 9. [PubMed:19066855 ]
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:
PDE4B
Uniprot ID:
Q07343
Molecular weight:
64351.765
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Xin ZC, Kim EK, Lin CS, Liu WJ, Tian L, Yuan YM, Fu J: Effects of icariin on cGMP-specific PDE5 and cAMP-specific PDE4 activities. Asian J Androl. 2003 Mar;5(1):15-8. [PubMed:12646997 ]
  4. Zhu S, Gan Z, Li Z, Liu Y, Yang X, Deng P, Xie Y, Yu M, Liao H, Zhao Y, Zhao L, Liao F: The measurement of cyclic nucleotide phosphodiesterase 4 activities via the quantification of inorganic phosphate with malachite green. Anal Chim Acta. 2009 Mar 16;636(1):105-10. doi: 10.1016/j.aca.2009.01.035. Epub 2009 Jan 22. [PubMed:19231363 ]