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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:51:33 UTC
Update Date2022-03-07 02:57:14 UTC
HMDB IDHMDB0041984
Secondary Accession Numbers
  • HMDB41984
Metabolite Identification
Common NamePholcodine
DescriptionPholcodine, also known as folcodina or ethnine, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Based on a literature review a significant number of articles have been published on Pholcodine.
Structure
Data?1563863719
Synonyms
ValueSource
3-(2-(4-Morpholinyl)ethyl)morphineChEBI
3-(2-Morpholinoethyl)morphineChEBI
3-MorpholinoethylmorphineChEBI
3-MorpholylaethylmorphinChEBI
7,8-Didehydro-4,5-alpha-epoxy-17-methyl-3-(2-morpholinoethoxy)morphinan-6-alpha-olChEBI
beta-MorpholinoethylmorphineChEBI
FolcodinaChEBI
MorpholinylethylmorphineChEBI
PholcodinumChEBI
Tetrahydro-1,4-oxazinylmethylcodeineChEBI
Pholcodine linctusKegg
7,8-Didehydro-4,5-a-epoxy-17-methyl-3-(2-morpholinoethoxy)morphinan-6-a-olGenerator
7,8-Didehydro-4,5-α-epoxy-17-methyl-3-(2-morpholinoethoxy)morphinan-6-α-olGenerator
b-MorpholinoethylmorphineGenerator
Β-morpholinoethylmorphineGenerator
(5alpha,6alpha)-17-Methyl-3-[2-(morpholin-4-yl)ethoxy]-7,8-didehydro-4,5-epoxymorphinan-6-olHMDB
03-(2-Morpholinoethyl)-morphineHMDB
3-MorpholylathylmorphinHMDB
3-O-(2-Morpholinoethyl)-morphineHMDB
beta-MorpholinylethylmorphineHMDB
CodylinHMDB
Dia-tussHMDB
EthnineHMDB
Ethnine simplexHMDB
FolcodineHMDB
FolkodinHMDB
GalenpholHMDB
GalpholHMDB
GlycodineHMDB
HibernylHMDB
HomocodeineHMDB
MemineHMDB
NeocodinHMDB
NeocodineHMDB
O3-(2-Morpholinoethyl)morphineHMDB
PectolinHMDB
PholcodinHMDB
PholtexHMDB
ProdromineHMDB
TussokonHMDB
WeifacodineHMDB
7,8-Didehydro-4,5 alpha-epoxy-17-methyl-3-(2-morpholinoethoxymorphinan-6 alpha-ol)HMDB
Chemical FormulaC23H30N2O4
Average Molecular Weight398.4953
Monoisotopic Molecular Weight398.220557458
IUPAC Name(1S,5R,13R,14S,17R)-4-methyl-10-[2-(morpholin-4-yl)ethoxy]-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-ol
Traditional Namememine
CAS Registry Number509-67-1
SMILES
[H][C@@]12OC3=C(OCCN4CCOCC4)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
InChI Identifier
InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3/t16-,17+,18-,22-,23-/m0/s1
InChI KeyGPFAJKDEDBRFOS-FKQDBXSBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • Aralkylamine
  • Morpholine
  • Oxazinane
  • Piperidine
  • Benzenoid
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Tertiary amine
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point91 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility20 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.49 g/LALOGPS
logP1.09ALOGPS
logP1.14ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.7 m³·mol⁻¹ChemAxon
Polarizability43.76 ųChemAxon
Number of Rings6ChemAxon
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]+192.80931661259
DarkChem[M-H]-187.10331661259
DeepCCS[M-2H]-227.78230932474
DeepCCS[M+Na]+204.13430932474
AllCCS[M+H]+197.532859911
AllCCS[M+H-H2O]+195.232859911
AllCCS[M+NH4]+199.732859911
AllCCS[M+Na]+200.332859911
AllCCS[M-H]-195.032859911
AllCCS[M+Na-2H]-195.332859911
AllCCS[M+HCOO]-195.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pholcodine[H][C@@]12OC3=C(OCCN4CCOCC4)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O3584.9Standard polar33892256
Pholcodine[H][C@@]12OC3=C(OCCN4CCOCC4)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O3103.9Standard non polar33892256
Pholcodine[H][C@@]12OC3=C(OCCN4CCOCC4)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O3182.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pholcodine,1TMS,isomer #1CN1CC[C@]23C4=C5C=CC(OCCN6CCOCC6)=C4O[C@H]2[C@@H](O[Si](C)(C)C)C=C[C@H]3[C@H]1C53108.7Semi standard non polar33892256
Pholcodine,1TBDMS,isomer #1CN1CC[C@]23C4=C5C=CC(OCCN6CCOCC6)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@H]3[C@H]1C53341.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pholcodine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4129000000-92c59129a2ae675805842017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pholcodine GC-MS (1 TMS) - 70eV, Positivesplash10-05dl-9105600000-da684da1fc185f1b46b12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pholcodine 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 - Pholcodine 10V, Positive-QTOFsplash10-0002-0109000000-6c9c5385ecb1bff25d8c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 20V, Positive-QTOFsplash10-03di-1914000000-10e6b649471cc94922132017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 40V, Positive-QTOFsplash10-06ri-9350000000-df114e727b126242ea4d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 10V, Negative-QTOFsplash10-0002-0029000000-55b574978391dfd6ae2f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 20V, Negative-QTOFsplash10-001j-1195000000-e176743a3b642da058042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 40V, Negative-QTOFsplash10-0040-5190000000-9b2b400b2a85cd5df3982017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 10V, Negative-QTOFsplash10-0002-0009000000-183bcb6ac115bb17c68a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 20V, Negative-QTOFsplash10-0002-0029000000-953276fefcb5eae036042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 40V, Negative-QTOFsplash10-001i-1091000000-d3b1b7f45c09dd40ab042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 10V, Positive-QTOFsplash10-0002-0009000000-0c36e5a0f1ec6d49ad1b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 20V, Positive-QTOFsplash10-0002-0209000000-098009a65eecf498b3e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pholcodine 40V, Positive-QTOFsplash10-03k9-7339000000-8afda55c39a1cf7ae4202021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB09209
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470854
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPholcodine
METLIN IDNot Available
PubChem Compound5311356
PDB IDNot Available
ChEBI ID53579
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 ReferencesNot Available