NP-MRD: Showing NP-Card for hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate (NP0283050)

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Record Information

Version

2.0

Created at

2022-09-09 10:08:46 UTC

Updated at

2022-09-09 10:08:47 UTC

NP-MRD ID

NP0283050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate

Description

(Hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulfanyl)prop-2-enoate belongs to the class of organic compounds known as pyrrolizidines. hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate is found in Planchonella thyrsoidea. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom (hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulfanyl)prop-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    7.0238    0.3479    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8840    0.6249    1.4020 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3325   -0.2165    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    0.2585    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866   -0.3593    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8799   -1.3926    0.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    0.1242   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0249   -0.4217   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273   -0.4158    0.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0658    0.9607    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831    0.8108    1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265   -0.5533    1.0799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2519   -0.5510    0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3881    0.0835   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -0.0313   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394   -0.8904   -0.2210 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1973   -0.7377   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9509    0.9062    0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5919    0.7997   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -1.1043    1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202    1.1316   -0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822    0.1641   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -1.4722   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989   -1.0525    0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0818    1.7278   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2226    1.1884    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    1.4978    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    1.0520    2.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.5981    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160    0.0648    1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7206    1.1302   -0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1761   -0.4609   -1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -0.6103   -2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    0.9434   -1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211   -1.9486   -0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16  9  1  0
 16 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  1
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  6
M  END


  Mrv1533004171518462D          

 16 17  0  0  0  0            999 V2000
   -2.7653   -1.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -2.3931    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063   -2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC=CC(=O)OCC1CCN2CCCC12

> <INCHI_IDENTIFIER>
InChI=1S/C12H19NO2S/c1-16-8-5-12(14)15-9-10-4-7-13-6-2-3-11(10)13/h5,8,10-11H,2-4,6-7,9H2,1H3

> <INCHI_KEY>
CSBNFFCXWVMDOG-UHFFFAOYSA-N

> <FORMULA>
C12H19NO2S

> <MOLECULAR_WEIGHT>
241.35

> <EXACT_MASS>
241.11365003

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.952145910449268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulfanyl)prop-2-enoate

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.6955402853333335

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.23354971825914

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
67.6901

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexahydro-1H-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

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      -5.162  -3.323   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -4.131  -4.467   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -2.625  -4.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.595  -5.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.942  -6.116   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.834   0.294   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   12                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(Hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulfanyl)prop-2-enoic acid	Generator
(Hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulphanyl)prop-2-enoate	Generator
(Hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulphanyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₂H₁₉NO₂S

Average Mass

241.3500 Da

Monoisotopic Mass

241.11365 Da

IUPAC Name

(hexahydro-1H-pyrrolizin-1-yl)methyl 3-(methylsulfanyl)prop-2-enoate

Traditional Name

hexahydro-1H-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CSC=CC(=O)OCC1CCN2CCCC12

InChI Identifier

InChI=1S/C12H19NO2S/c1-16-8-5-12(14)15-9-10-4-7-13-6-2-3-11(10)13/h5,8,10-11H,2-4,6-7,9H2,1H3

InChI Key

CSBNFFCXWVMDOG-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
Planchonella thyrsoidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
N-alkylpyrrolidine
Vinylogous thioester
Pyrrolidine
Acrylic acid or derivatives
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Thioenolether
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Sulfenyl compound
Azacycle
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.8	ALOGPS
logP	1.7	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.69 m³·mol⁻¹	ChemAxon
Polarizability	26.95 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate (NP0283050)

MOL for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

3D MOL for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

3D SDF for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

3D-SDF for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

PDB for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

3D PDB for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

SMILES for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

INCHI for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

Structure for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)

3D Structure for NP0283050 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(methylsulfanyl)prop-2-enoate)