NP-MRD: Showing NP-Card for {5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate (NP0158863)

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Record Information

Version

2.0

Created at

2022-09-02 16:31:34 UTC

Updated at

2022-09-02 16:31:34 UTC

NP-MRD ID

NP0158863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate

Description

{5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate is found in Santolina chamaecyparissus and Santolina rosmarinifolia.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -7.1435    1.0325    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8639   -0.4100   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9129   -1.3198    0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4751   -0.7790    0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4798    0.0515   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    0.9053   -1.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1329   -0.0676   -0.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662    0.7093   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    0.3078   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269   -0.6386    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719   -0.8381    0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -0.0797    0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1448   -0.1042    0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.1079    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7709   -0.1093    0.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5850    0.3711   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0354    0.3836   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9354    0.8709   -0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2073    0.6935   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9950    0.1040    0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6895   -0.0673    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.8859   -0.7392 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9996    1.1571    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4466    1.5558   -0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2330    1.5026    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8836   -0.5798   -1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5112   -2.3609    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8036   -1.2812   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1549   -1.0711    1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3433   -1.8726    0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3551   -0.6727    1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400    0.4709   -1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766    1.7663   -0.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3563   -1.2101    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -1.5845    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361   -0.5035    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244    0.7642   -1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7313    1.3176   -1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1558    0.9690   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8109   -0.1608    1.5043 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 22  1  0
 12 13  1  0
 13 14  3  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 22  9  1  0
 21 17  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
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END


  Mrv1652309022218312D          

 22 23  0  0  0  0            999 V2000
    4.5113   -7.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2258   -7.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2258   -8.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9403   -7.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6548   -7.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6548   -8.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3692   -7.3281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0837   -7.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7982   -7.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8844   -6.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6914   -6.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1039   -7.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9244   -7.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7448   -7.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5653   -7.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0502   -6.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8707   -6.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4228   -6.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1764   -6.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0902   -7.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2832   -7.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5518   -7.6637    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  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
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 12 22  1  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OCC1=CC=C(S1)C#C\C=C\C1=CC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O3S/c1-14(2)12-18(19)21-13-17-10-9-16(22-17)8-4-3-6-15-7-5-11-20-15/h3,5-7,9-11,14H,12-13H2,1-2H3/b6-3+

> <INCHI_KEY>
OPCASUWOGKPNAT-ZZXKWVIFSA-N

> <FORMULA>
C18H18O3S

> <MOLECULAR_WEIGHT>
314.4

> <EXACT_MASS>
314.097665614

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
35.556599963624656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-[(3E)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
4.915697534333333

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8700844937590357

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
85.9535

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-[(3E)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.421 -13.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.755 -14.449   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.755 -15.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.089 -13.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.422 -14.449   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.422 -15.989   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.756 -13.679   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.090 -14.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.423 -13.679   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.584 -12.148   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.091 -11.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.861 -13.161   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.392 -13.322   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.924 -13.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.455 -13.644   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.360 -12.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.892 -12.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.922 -11.415   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.329 -12.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.168 -13.573   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      26.662 -13.893   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0      17.830 -14.306   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
CONECT   22   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₃S

Average Mass

314.4000 Da

Monoisotopic Mass

314.09767 Da

IUPAC Name

{5-[(3E)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate

Traditional Name

{5-[(3E)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OCC1=CC=C(S1)C#C\C=C\C1=CC=CO1

InChI Identifier

InChI=1S/C18H18O3S/c1-14(2)12-18(19)21-13-17-10-9-16(22-17)8-4-3-6-15-7-5-11-20-15/h3,5-7,9-11,14H,12-13H2,1-2H3/b6-3+

InChI Key

OPCASUWOGKPNAT-ZZXKWVIFSA-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
Santolina chamaecyparissus	LOTUS Database	35616633
Santolina rosmarinifolia	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	5.28	ALOGPS
logP	4.92	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.95 m³·mol⁻¹	ChemAxon
Polarizability	35.56 Å³	ChemAxon
Number of Rings	2	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate (NP0158863)

MOL for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

3D MOL for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

3D SDF for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

3D-SDF for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

PDB for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

3D PDB for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

SMILES for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

INCHI for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

Structure for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)

3D Structure for NP0158863 ({5-[(3e)-4-(furan-2-yl)but-3-en-1-yn-1-yl]thiophen-2-yl}methyl 3-methylbutanoate)