NP-MRD: Showing NP-Card for 1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate (NP0223071)

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Record Information

Version

2.0

Created at

2022-09-06 01:03:59 UTC

Updated at

2022-09-06 01:03:59 UTC

NP-MRD ID

NP0223071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate

Description

5-(3,4-Diacetoxybut-1-ynyl)-2,2'-bithiophene 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. Thus, 5-(3,4-diacetoxybut-1-ynyl)-2,2'-bithiophene is considered to be an oxygenated hydrocarbon lipid molecule. 1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate is found in Echinops ritro. 5-(3,4-Diacetoxybut-1-ynyl)-2,2'-bithiophene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171520532D          

 22 23  0  0  0  0            999 V2000
    3.1702   -5.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5827   -4.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702   -4.1652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -4.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202   -4.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6452   -4.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -4.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8827   -4.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2952   -4.1652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2952   -5.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -3.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4702   -2.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8827   -2.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5471   -1.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8747   -1.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7032   -1.9356    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6284   -0.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7999    0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6204    0.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9560   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3429   -1.2055    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  1  0  0  0  0
  5  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
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  3  0  0  0  0
 12 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>
NP0223071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(OC(C)=O)C#CC1=CC=C(S1)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4S2/c1-11(17)19-10-13(20-12(2)18)5-6-14-7-8-16(22-14)15-4-3-9-21-15/h3-4,7-9,13H,10H2,1-2H3

> <INCHI_KEY>
RGIIXLVKXLFDLP-UHFFFAOYSA-N

> <FORMULA>
C16H14O4S2

> <MOLECULAR_WEIGHT>
334.4

> <EXACT_MASS>
334.033351279

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
35.36479280342871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(acetyloxy)-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-2-yl acetate

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.2656167833333325

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.11707387204823

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7199595333764135

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
81.4714

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(acetyloxy)-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.918 -10.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.688  -9.109   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.918  -7.775   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.228  -9.109   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.998  -7.775   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.538  -7.775   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.308  -9.109   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.848  -9.109   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.618  -7.775   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.618 -10.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.308  -6.441   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.078  -5.108   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.848  -3.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.221  -2.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.366  -1.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.699  -2.107   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0      14.379  -3.613   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0      16.106  -1.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.427   0.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.958   0.187   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.584  -1.220   0.000  0.00  0.00           C+0
HETATM   22  S   UNK     0      17.440  -2.250   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   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   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄S₂

Average Mass

334.4000 Da

Monoisotopic Mass

334.03335 Da

IUPAC Name

1-(acetyloxy)-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-2-yl acetate

Traditional Name

1-(acetyloxy)-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC(OC(C)=O)C#CC1=CC=C(S1)C1=CC=CS1

InChI Identifier

InChI=1S/C16H14O4S2/c1-11(17)19-10-13(20-12(2)18)5-6-14-7-8-16(22-14)15-4-3-9-21-15/h3-4,7-9,13H,10H2,1-2H3

InChI Key

RGIIXLVKXLFDLP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Echinops ritro	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
Dicarboxylic acid or derivatives
Heteroaromatic compound
Thiophene
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

acetate ester (CHEBI:16013 )
acetylenic compound (CHEBI:16013 )
2,2'-bithiophenes (CHEBI:16013 )
a small molecule (5-34-DIACETOXYBUT-1-YNYL-22-BITHIOP )

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	3.62	ALOGPS
logP	3.27	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	81.47 m³·mol⁻¹	ChemAxon
Polarizability	35.36 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

C00049955

Chemspider ID

Not Available

KEGG Compound ID

C04606

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440404

PDB ID

Not Available

ChEBI ID

16013

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate (NP0223071)

MOL for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

3D MOL for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

3D SDF for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

3D-SDF for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

PDB for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

3D PDB for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

SMILES for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

INCHI for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

Structure for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)

3D Structure for NP0223071 (1-(acetyloxy)-4-{[2,2'-bithiophen]-5-yl}but-3-yn-2-yl acetate)