NP-MRD: Showing NP-Card for 1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate (NP0255713)

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Record Information

Version

2.0

Created at

2022-09-07 20:17:44 UTC

Updated at

2022-09-07 20:17:44 UTC

NP-MRD ID

NP0255713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate

Description

1-[3-(Butan-2-yldisulfanyl)prop-2-en-1-yl] 3-tert-butyl propanedioate belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate is found in Ferula persica. 1-[3-(Butan-2-yldisulfanyl)prop-2-en-1-yl] 3-tert-butyl propanedioate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 43  0  0  0  0  0  0  0  0999 V2000
    7.2709    1.4934    0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5859    0.0358    0.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4347   -0.8605    0.1970 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8314   -2.2891    0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0440   -0.4849    1.3106 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809    1.4707    0.8217 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956    1.1497   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133    0.5407   -0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    0.1687   -0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4013    0.8399   -0.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725    0.5959   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055   -0.2453   -1.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198    1.2177   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136    0.2456   -0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977   -0.9686   -0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2615    0.6923    0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3704   -0.1631    0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7114   -0.9969   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5608    0.7923    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1031   -0.9566    1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1973    2.1072    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8776    1.9096    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5450    1.7008   -0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5099   -0.2459    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8281   -0.1666    1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1026   -0.6246   -0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564   -2.9701   -0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8929   -2.5596    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8267   -2.4438   -0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937    1.4864   -1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    0.2557    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    0.4816   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044   -0.9238   -0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8174    1.8115    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    1.9605   -1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0916   -0.6678   -1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4380   -2.0561   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7828   -0.9406   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4191    1.4150    1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6050    1.3678   -0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4576    0.1553    0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7064   -1.8650    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135   -1.1740    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3507   -0.2909    2.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 13 34  1  0
 13 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END


  Mrv1533004261505232D          

 20 19  0  0  0  0            999 V2000
   -4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.8414    0.0000 C   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)SSC=CCOC(=O)CC(=O)OC(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O4S2/c1-6-11(2)20-19-9-7-8-17-12(15)10-13(16)18-14(3,4)5/h7,9,11H,6,8,10H2,1-5H3

> <INCHI_KEY>
HPCAZZNSODRLCQ-UHFFFAOYSA-N

> <FORMULA>
C14H24O4S2

> <MOLECULAR_WEIGHT>
320.46

> <EXACT_MASS>
320.111601601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.899501877192684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[3-(butan-2-yldisulfanyl)prop-2-en-1-yl] 3-tert-butyl propanedioate

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
3.5840807029999997

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.293260483965467

> <JCHEM_PKA_STRONGEST_BASIC>
-6.860001434231768

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
86.00370000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -8.359   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.692  -0.206   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      -4.358   2.104   0.000  0.00  0.00           S+0
HETATM    6  S   UNK     0      -3.025   1.334   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.645   1.334   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.312   2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.208   3.437   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
1-[3-(Butan-2-yldisulfanyl)prop-2-en-1-yl] 3-tert-butyl propanedioic acid	Generator
1-[3-(Butan-2-yldisulphanyl)prop-2-en-1-yl] 3-tert-butyl propanedioate	Generator
1-[3-(Butan-2-yldisulphanyl)prop-2-en-1-yl] 3-tert-butyl propanedioic acid	Generator

Chemical Formula

C₁₄H₂₄O₄S₂

Average Mass

320.4600 Da

Monoisotopic Mass

320.11160 Da

IUPAC Name

1-[3-(butan-2-yldisulfanyl)prop-2-en-1-yl] 3-tert-butyl propanedioate

Traditional Name

1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate

CAS Registry Number

Not Available

SMILES

CCC(C)SSC=CCOC(=O)CC(=O)OC(C)(C)C

InChI Identifier

InChI=1S/C14H24O4S2/c1-6-11(2)20-19-9-7-8-17-12(15)10-13(16)18-14(3,4)5/h7,9,11H,6,8,10H2,1-5H3

InChI Key

HPCAZZNSODRLCQ-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
Ferula persica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Organic disulfide
Carboxylic acid ester
Sulfenyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	5.19	ALOGPS
logP	3.58	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-6.9	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	11	ChemAxon
Refractivity	86 m³·mol⁻¹	ChemAxon
Polarizability	33.9 Å³	ChemAxon
Number of Rings	0	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

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

73064917

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate (NP0255713)

MOL for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

3D MOL for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

3D SDF for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

3D-SDF for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

PDB for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

3D PDB for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

SMILES for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

INCHI for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

Structure for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)

3D Structure for NP0255713 (1-tert-butyl 3-[3-(sec-butyldisulfanyl)prop-2-en-1-yl] propanedioate)