Showing Compound Card for Dothiepin sulfoxide (CDB000787)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (5) Show 13 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:56:58 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000787
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDothiepin sulfoxide
DescriptionDothiepin sulfoxide or 1-Propanamine, 3-dibenzo [b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-, S-oxide belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.  Dothiepin sulfoxide is a tricyclic compound and possesses three rings fused together with a side chain attached in its chemical structure. Dothiepin sulfoxide is a very strong basic compound (based on its pKa). Dothiepin sulfoxide is a drug and an oxidation product of Dosulepin. Dosulepin is a drug used in the treatment of depression. It is not FDA-approved due to low therpeutic index and significant toxicity in overdose. Dosulepin inhibits the reuptake of biogenic amines, increasing available neurotransmitter levels at the synaptic cleft. Dosulepin exhibits anticholinergic, antihistamine and central sedative properties (Drugbank).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC19H21NOS
Average Molecular Weight311.44
Monoisotopic Molecular Weight311.1344
IUPAC Name(2E,9R)-2-[3-(dimethylamino)propylidene]-9lambda4-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-9-one
Traditional Name(2E,9R)-2-[3-(dimethylamino)propylidene]-9lambda4-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-9-one
CAS Registry NumberNot Available
SMILES
CN(C)CC\C=C1/C2=CC=CC=C2C[S@@](=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C19H21NOS/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-22(21)19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+/t22-/m1/s1
InChI KeyNBNPVRZHUPMVQS-JRVGGCGHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiepins
Sub ClassDibenzothiepins
Direct ParentDibenzothiepins
Alternative Parents
Substituents
  • Dibenzothiepin
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Sulfoxide
  • Sulfinyl compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.32ALOGPS
logP2.88ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)19.48ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.12 m³·mol⁻¹ChemAxon
Polarizability35.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-2B adrenergic receptorADRA2B2p13-q13P18089 details
TransthyretinTTR18q12.1P02766 details
5-hydroxytryptamine receptor 1AHTR1A5q11.2-q13P08908 details
Histamine H1 receptorHRH13p25P35367 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
Cytochrome P450 2D6CYP2D622q13.1P10635 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-2B adrenergic receptorADRA2B2p13-q13P18089 details
5-hydroxytryptamine receptor 1AHTR1A5q11.2-q13P08908 details
5-hydroxytryptamine receptor 2AHTR2A13q14-q21P28223 details
Histamine H1 receptorHRH13p25P35367 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 Compound92279071
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details
1. Alpha-2A adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
Enzyme Details
2. Alpha-2B adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
Enzyme Details
3. Transthyretin
General function:
Involved in hormone activity
Specific function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain
Gene Name:
TTR
Uniprot ID:
P02766
Molecular weight:
15886.9
Enzyme Details
4. 5-hydroxytryptamine receptor 1A
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
Enzyme Details
5. Histamine H1 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6

Only showing the first 10 proteins. There are 13 proteins in total.

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