NP-MRD: Showing NP-Card for Thienodolin (NP0050911)

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Record Information

Version

1.0

Created at

2022-04-27 22:22:50 UTC

Updated at

2022-04-27 22:22:50 UTC

NP-MRD ID

NP0050911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thienodolin

Description

Thienodolin belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Thienodolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Thienodolin is found in Apis cerana, Streptomyces alboflavus, Streptomyces albogriseolus and Trypanosoma brucei. It was first documented in 2012 (PMID: 22816309). An indole alkaloid that is a thienoindole ring with carboxamide group and chlorine substituents at positions 2 and 6 respectively.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251515332D          

 16 18  0  0  0  0            999 V2000
   -0.8294   -1.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2056   -1.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -0.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -1.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -1.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333   -1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1008   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436   -2.2020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959   -2.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -2.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -2.3868    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=CC2=C(NC3=CC(Cl)=CC=C23)S1

> <INCHI_IDENTIFIER>
InChI=1S/C11H7ClN2OS/c12-5-1-2-6-7-4-9(10(13)15)16-11(7)14-8(6)3-5/h1-4,14H,(H2,13,15)

> <INCHI_KEY>
LREDECYEGMWOAR-UHFFFAOYSA-N

> <FORMULA>
C11H7ClN2OS

> <MOLECULAR_WEIGHT>
250.7

> <EXACT_MASS>
249.9967617

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
24.925412965412477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-chloro-8H-thieno[2,3-b]indole-2-carboxamide

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.8137555486666668

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.155133697445777

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.600070913067052

> <JCHEM_PKA_STRONGEST_BASIC>
-1.629384702414435

> <JCHEM_POLAR_SURFACE_AREA>
58.88

> <JCHEM_REFRACTIVITY>
63.1698

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thienodolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  N   UNK     0      -1.548  -3.485   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.384  -2.477   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.674  -0.965   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.071  -2.982   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.335  -2.101   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.562  -3.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.102  -3.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.155  -1.937   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.655  -2.287   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.102  -3.761   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       9.601  -4.110   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       7.049  -4.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.549  -4.535   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.286  -5.415   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.058  -4.486   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       1.518  -4.455   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₇ClN₂OS

Average Mass

250.7000 Da

Monoisotopic Mass

249.99676 Da

IUPAC Name

6-chloro-8H-thieno[2,3-b]indole-2-carboxamide

Traditional Name

thienodolin

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CC2=C(NC3=CC(Cl)=CC=C23)S1

InChI Identifier

InChI=1S/C11H7ClN2OS/c12-5-1-2-6-7-4-9(10(13)15)16-11(7)14-8(6)3-5/h1-4,14H,(H2,13,15)

InChI Key

LREDECYEGMWOAR-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, 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
Apis cerana	LOTUS Database	35616633
Streptomyces alboflavus	LOTUS Database	35616633
Streptomyces albogriseolus	Bacteria	KNApSAcK
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
2-heteroaryl carboxamide
Thienopyrrole
Thiophene carboxamide
Thiophene carboxylic acid or derivatives
2,3,5-trisubstituted thiophene
Benzenoid
Aryl halide
Aryl chloride
Heteroaromatic compound
Thiophene
Azole
Pyrrole
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:9543 )
organic heterotricyclic compound (CHEBI:9543 )
organochlorine compound (CHEBI:9543 )
indole alkaloid (CHEBI:9543 )
aromatic amide (CHEBI:9543 )
organosulfur heterocyclic compound (CHEBI:9543 )

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	2.67	ALOGPS
logP	2.81	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.6	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.88 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.17 m³·mol⁻¹	ChemAxon
Polarizability	24.93 Å³	ChemAxon
Number of Rings	3	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

C00001775

Chemspider ID

Not Available

KEGG Compound ID

C09245

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442119

PDB ID

Not Available

ChEBI ID

9543

Good Scents ID

Not Available

References

General References

Park EJ, Pezzuto JM, Jang KH, Nam SJ, Bucarey SA, Fenical W: Suppression of nitric oxide synthase by thienodolin in lipopolysaccharide-stimulated RAW 264.7 murine macrophage cells. Nat Prod Commun. 2012 Jun;7(6):789-94. [PubMed:22816309 ]

Showing NP-Card for Thienodolin (NP0050911)

MOL for NP0050911 (Thienodolin)

3D MOL for NP0050911 (Thienodolin)

3D SDF for NP0050911 (Thienodolin)

3D-SDF for NP0050911 (Thienodolin)

PDB for NP0050911 (Thienodolin)

3D PDB for NP0050911 (Thienodolin)

SMILES for NP0050911 (Thienodolin)

INCHI for NP0050911 (Thienodolin)

Structure for NP0050911 (Thienodolin)

3D Structure for NP0050911 (Thienodolin)