NP-MRD: Showing NP-Card for Dothiepin sulfoxide (NP0045228)

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Record Information

Version

2.0

Created at

2022-03-10 19:01:38 UTC

Updated at

2022-03-10 22:20:34 UTC

NP-MRD ID

NP0045228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dothiepin sulfoxide

Description

Dothiepin 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

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    3.2845    1.8422    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.5134    0.5068 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539    0.2588    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8670   -0.5451   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832   -0.7188    0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4901    0.3233    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196    0.1144   -0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980   -1.2613   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522   -1.8078   -1.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -3.1265   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240   -3.8370   -1.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377   -3.2435   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639   -1.8887   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307   -1.5517    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    0.0266    1.2700 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2192   -0.0241    2.7077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119    1.2785    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    2.4834    0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851    3.5856   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665    3.5566   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9618    2.3758   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6291    1.3105   -0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556    2.4027   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467    2.3843    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346    1.9415   -0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6640    1.0275    0.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745   -0.7178    0.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4030    0.1249    1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411   -0.4013   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -1.4857    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7628   -0.5733    1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -1.7408    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603    1.3537    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665   -1.2379   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308   -3.5884   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -4.8867   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236   -3.8187   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426   -2.3279    1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784   -1.8715   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    2.5312    0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316    4.5383   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2232    4.4473   -1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    2.2341   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 15 14  1  6
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END


  Mrv1652303192001393D          

 22 24  0  0  0  0            999 V2000
    4.5436    0.4129    1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245   -0.2940   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -3.8563   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -3.2149   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    3.2929   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904    3.3362   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -0.1848   -0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -3.0946    0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2173   -1.8305   -1.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044    2.2727   -1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747    0.7103   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643    2.3515   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4783    0.5693    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -1.1919    1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.7182    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -1.1447   -0.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8435    0.2966   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9346    1.3170   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    1.3064    0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -0.1839    0.6443 N   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1652    0.8662    2.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    0.2027    1.3617 S   0  0  2  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  8 15  2  0  0  0  0
  9 16  2  0  0  0  0
 10 18  2  0  0  0  0
 11 17  2  0  0  0  0
 12 19  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045228

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
NBNPVRZHUPMVQS-JRVGGCGHSA-N

> <FORMULA>
C19H21NOS

> <MOLECULAR_WEIGHT>
311.44

> <EXACT_MASS>
311.134385474

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.33264505907384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
2.8832491963333338

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.47894869231717

> <JCHEM_PKA_STRONGEST_BASIC>
9.060738670054455

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
106.1154

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0       4.544   0.413   1.602  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.425  -0.294  -0.611  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.971  -3.856  -0.079  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.222  -3.215  -1.051  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516   3.293  -1.683  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.690   3.336  -0.927  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.529  -0.185  -0.584  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.738  -3.095   0.811  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.217  -1.831  -1.160  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.604   2.273  -1.536  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.375   0.710  -0.700  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.964   2.352  -0.010  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.478   0.569   0.433  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.649  -1.192   1.761  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.763  -1.718   0.742  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.987  -1.145  -0.258  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.844   0.297  -0.545  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.935   1.317  -0.601  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.066   1.306   0.166  0.00  0.00           C+0
HETATM   20  N   UNK     0       3.662  -0.184   0.644  0.00  0.00           N+0
HETATM   21  O   UNK     0      -4.165   0.866   2.620  0.00  0.00           O+0
HETATM   22  S   UNK     0      -3.632   0.203   1.362  0.00  0.00           S+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7   11   13                                                       
CONECT    8    3   15                                                       
CONECT    9    4   16                                                       
CONECT   10    5   18                                                       
CONECT   11    7   17                                                       
CONECT   12    6   19                                                       
CONECT   13    7   20                                                       
CONECT   14   15   22                                                       
CONECT   15    8   14   16                                                  
CONECT   16    9   15   17                                                  
CONECT   17   11   16   18                                                  
CONECT   18   10   17   19                                                  
CONECT   19   12   18   22                                                  
CONECT   20    1    2   13                                                  
CONECT   21   22                                                            
CONECT   22   14   19   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NOS

Average Mass

311.4400 Da

Monoisotopic Mass

311.13439 Da

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 Number

Not 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 Key

NBNPVRZHUPMVQS-JRVGGCGHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	NULL	Not Available

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiepins

Sub Class

Dibenzothiepins

Direct Parent

Dibenzothiepins

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.32	ALOGPS
logP	2.88	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.48	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.12 m³·mol⁻¹	ChemAxon
Polarizability	35.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92279071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dothiepin sulfoxide (NP0045228)

MOL for NP0045228 (Dothiepin sulfoxide)

3D MOL for NP0045228 (Dothiepin sulfoxide)

3D SDF for NP0045228 (Dothiepin sulfoxide)

3D-SDF for NP0045228 (Dothiepin sulfoxide)

PDB for NP0045228 (Dothiepin sulfoxide)

3D PDB for NP0045228 (Dothiepin sulfoxide)

SMILES for NP0045228 (Dothiepin sulfoxide)

INCHI for NP0045228 (Dothiepin sulfoxide)

Structure for NP0045228 (Dothiepin sulfoxide)

3D Structure for NP0045228 (Dothiepin sulfoxide)