NP-MRD: Showing NP-Card for 9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol (NP0213123)

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Record Information

Version

2.0

Created at

2022-09-05 12:00:33 UTC

Updated at

2022-09-05 12:00:33 UTC

NP-MRD ID

NP0213123

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol

Description

Lissoclinotoxin A belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. 9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol is found in Lissoclinum perforatum. Based on a literature review very few articles have been published on Lissoclinotoxin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -4.0356   -0.1689   -0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4298   -0.1438    0.3391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298   -0.2592    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371   -1.4964    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2114   -2.6473    0.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -1.5608    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.4149    0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -0.5687    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103   -0.4139   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3423   -0.5818   -0.3456 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    0.7955    0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    0.9207    0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    2.3177    0.2490 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466    4.1343    0.9459 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    4.9183   -0.5975 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1109    3.3668   -1.1675 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    2.0935    0.5460 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655    0.7330   -1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -0.1281   -1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -1.0418   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -3.5337    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4309   -2.5050    0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.1646    1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4525   -1.5682    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5841   -1.1931   -1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600    0.6062   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.2554   -1.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5653   -1.5693   -0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12  3  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
M  END


  Mrv1652309052214002D          

 17 18  0  0  0  0            999 V2000
    0.5915    1.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    0.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -2.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -2.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -3.7033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.1111    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -0.0725    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -0.8158    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -1.5591    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365   -1.7427    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213123

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(CCN)C2=C1SSSSS2

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO2S5/c1-12-7-6(11)4-5(2-3-10)8-9(7)14-16-17-15-13-8/h4,11H,2-3,10H2,1H3

> <INCHI_KEY>
WQAHCFFHBFQTRE-UHFFFAOYSA-N

> <FORMULA>
C9H11NO2S5

> <MOLECULAR_WEIGHT>
325.49

> <EXACT_MASS>
324.939334468

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
30.929411207569434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol

> <JCHEM_LOGP>
2.692142536241793

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.325079858937897

> <JCHEM_PKA_STRONGEST_BASIC>
9.978077687476244

> <JCHEM_POLAR_SURFACE_AREA>
55.480000000000004

> <JCHEM_REFRACTIVITY>
75.3421

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.104   2.327   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.230   1.557   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.230   0.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.563  -0.753   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.897   0.017   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.563  -2.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.230  -3.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.230  -4.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.563  -5.373   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.563  -6.913   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.104  -2.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.104  -0.753   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0       2.308   0.207   0.000  0.00  0.00           S+0
HETATM   14  S   UNK     0       3.810  -0.135   0.000  0.00  0.00           S+0
HETATM   15  S   UNK     0       4.478  -1.523   0.000  0.00  0.00           S+0
HETATM   16  S   UNK     0       3.810  -2.910   0.000  0.00  0.00           S+0
HETATM   17  S   UNK     0       2.308  -3.253   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   17                                                  
CONECT   12   11    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₁NO₂S₅

Average Mass

325.4900 Da

Monoisotopic Mass

324.93933 Da

IUPAC Name

9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol

Traditional Name

9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(CCN)C2=C1SSSSS2

InChI Identifier

InChI=1S/C9H11NO2S5/c1-12-7-6(11)4-5(2-3-10)8-9(7)14-16-17-15-13-8/h4,11H,2-3,10H2,1H3

InChI Key

WQAHCFFHBFQTRE-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Lissoclinum perforatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
Anisole
Phenol ether
2-arylethylamine
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Ether
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
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	2.69	ChemAxon
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	9.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.34 m³·mol⁻¹	ChemAxon
Polarizability	30.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

8646993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10471582

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol (NP0213123)

MOL for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

3D MOL for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

3D SDF for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

3D-SDF for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

PDB for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

3D PDB for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

SMILES for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

INCHI for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

Structure for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)

3D Structure for NP0213123 (9-(2-aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol)