NP-MRD: Showing NP-Card for (5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate (NP0248021)

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Record Information

Version

2.0

Created at

2022-09-07 10:05:55 UTC

Updated at

2022-09-07 10:05:55 UTC

NP-MRD ID

NP0248021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate

Description

[5'-(Thiophen-2-yl)-[2,2'-bithiophene]-5-yl]methyl 2-methylpropanoate belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms. (5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate is found in Eclipta alba. [5'-(Thiophen-2-yl)-[2,2'-bithiophene]-5-yl]methyl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -6.3937   -0.5790    1.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091    0.2177    1.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4951    1.6794    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -0.0608    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823    0.8763   -0.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095   -1.3146   -0.0994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331   -1.6649   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.9801   -1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3726    0.1501   -1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    0.5716   -1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7437   -0.1603   -1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822    0.0893   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9584    1.1062   -1.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    1.1268   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    0.1289   -0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0254   -0.0399    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4649   -1.0278    1.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7496   -0.9908    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5193    0.0317    1.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4161    0.9087    0.1944 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2597   -0.8042    0.1297 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526   -1.4125   -0.5202 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1745   -1.5395    0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1706   -0.0665    0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8103   -0.7790    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028   -0.0004    2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9927    1.9864    2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5984    2.3454    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333    1.8922    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.5017   -2.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827   -2.7840   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    0.6659   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398    1.4876   -2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    1.8783   -2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548    1.9167   -1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579   -1.8151    1.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2134   -1.7456    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5911    0.2076    1.3615 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 22  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 21  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 22  8  1  0
 21 12  1  0
 20 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END


  Mrv1533004181500582D          

 22 24  0  0  0  0            999 V2000
    4.3947   -3.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1092   -3.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1092   -2.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8237   -3.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8237   -4.5564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   -3.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2526   -3.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9671   -3.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0533   -2.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8603   -2.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2728   -3.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7208   -3.6545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0933   -3.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6453   -2.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3990   -2.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3127   -3.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5058   -3.8421    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9258   -4.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7328   -4.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1453   -4.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5933   -5.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8396   -5.0430    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OCC1=CC=C(S1)C1=CC=C(S1)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O2S3/c1-11(2)17(18)19-10-12-5-6-15(21-12)16-8-7-14(22-16)13-4-3-9-20-13/h3-9,11H,10H2,1-2H3

> <INCHI_KEY>
SMZQYMVRMWFMGB-UHFFFAOYSA-N

> <FORMULA>
C17H16O2S3

> <MOLECULAR_WEIGHT>
348.49

> <EXACT_MASS>
348.031243277

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
38.36796681663919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{5-[5-(thiophen-2-yl)thiophen-2-yl]thiophen-2-yl}methyl 2-methylpropanoate

> <ALOGPS_LOGP>
5.85

> <JCHEM_LOGP>
5.645583933999999

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.079209014464197

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
91.73710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-[5-(thiophen-2-yl)thiophen-2-yl]thiophen-2-yl}methyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       8.203  -6.965   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.537  -6.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.537  -4.655   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.871  -6.965   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.871  -8.505   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.205  -6.195   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.538  -6.965   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.872  -6.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.033  -4.664   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.539  -4.344   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.309  -5.677   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      16.279  -6.822   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      18.841  -5.838   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.871  -4.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.278  -5.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.117  -6.852   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0      19.611  -7.172   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0      22.262  -7.882   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.768  -7.562   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.538  -8.896   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.507 -10.040   0.000  0.00  0.00           C+0
HETATM   22  S   UNK     0      22.101  -9.414   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    8                                                       
CONECT   13   11   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   13                                                       
CONECT   18   16   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
[5'-(Thiophen-2-yl)-[2,2'-bithiophene]-5-yl]methyl 2-methylpropanoic acid	Generator
Isobutyrate (2,2':5',2''-terthiophen-5-yl)methyl ester	Generator

Chemical Formula

C₁₇H₁₆O₂S₃

Average Mass

348.4900 Da

Monoisotopic Mass

348.03124 Da

IUPAC Name

{5-[5-(thiophen-2-yl)thiophen-2-yl]thiophen-2-yl}methyl 2-methylpropanoate

Traditional Name

{5-[5-(thiophen-2-yl)thiophen-2-yl]thiophen-2-yl}methyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OCC1=CC=C(S1)C1=CC=C(S1)C1=CC=CS1

InChI Identifier

InChI=1S/C17H16O2S3/c1-11(2)17(18)19-10-12-5-6-15(21-12)16-8-7-14(22-16)13-4-3-9-20-13/h3-9,11H,10H2,1-2H3

InChI Key

SMZQYMVRMWFMGB-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
Eclipta alba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Bi- and oligothiophenes

Sub Class

Not Available

Direct Parent

Bi- and oligothiophenes

Alternative Parents

Substituents

Bithiophene
2,5-disubstituted thiophene
Heteroaromatic compound
Thiophene
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.85	ALOGPS
logP	5.65	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.74 m³·mol⁻¹	ChemAxon
Polarizability	38.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

85772268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate (NP0248021)

MOL for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

3D MOL for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

3D SDF for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

3D-SDF for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

PDB for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

3D PDB for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

SMILES for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

INCHI for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

Structure for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)

3D Structure for NP0248021 ((5-{[2,2'-bithiophen]-5-yl}thiophen-2-yl)methyl 2-methylpropanoate)