NP-MRD: Showing NP-Card for S-Japonin (NP0048330)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:44 UTC

Updated at

2022-03-17 20:54:44 UTC

NP-MRD ID

NP0048330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

S-Japonin

Description

S-Japonin belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. S-Japonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, S-Japonin has been detected, but not quantified in, giant butterburs and green vegetables. This could make S-japonin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308432D          

 23 24  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18  6  1  0  0  0  0
 19  4  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23  5  1  0  0  0  0
 23  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS\C=C\C(=O)OC1CC(C)C2(C)CC(=C(C)C)C(=O)CC2C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3S/c1-12(2)16-11-19(4)13(3)8-15(9-14(19)10-17(16)20)22-18(21)6-7-23-5/h6-7,13-15H,8-11H2,1-5H3/b7-6+

> <INCHI_KEY>
HDHDUJDLKYTRAS-VOTSOKGWSA-N

> <FORMULA>
C19H28O3S

> <MOLECULAR_WEIGHT>
336.489

> <EXACT_MASS>
336.175915452

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.1476784877848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4a-dimethyl-7-oxo-6-(propan-2-ylidene)-decahydronaphthalen-2-yl (2E)-3-(methylsulfanyl)prop-2-enoate

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
4.433453369333334

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.480897859462252

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
96.41929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4a-dimethyl-7-oxo-6-(propan-2-ylidene)-hexahydro-1H-naphthalen-2-yl (2E)-3-(methylsulfanyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0      -2.667   4.620   0.000  0.00  0.00           S+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   19                                                            
CONECT    5   23                                                            
CONECT    6    7   18                                                       
CONECT    7    6   23                                                       
CONECT    8   13   15                                                       
CONECT    9   14   15                                                       
CONECT   10   14   17                                                       
CONECT   11   16   19                                                       
CONECT   12    1    2   16                                                  
CONECT   13    3    8   19                                                  
CONECT   14    9   10   19                                                  
CONECT   15    8    9   22                                                  
CONECT   16   11   12   17                                                  
CONECT   17   10   16   20                                                  
CONECT   18    6   21   22                                                  
CONECT   19    4   11   13   14                                             
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   15   18                                                       
CONECT   23    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
4,4a-Dimethyl-7-oxo-6-(propan-2-ylidene)-decahydronaphthalen-2-yl (2E)-3-(methylsulfanyl)prop-2-enoic acid	Generator
4,4a-Dimethyl-7-oxo-6-(propan-2-ylidene)-decahydronaphthalen-2-yl (2E)-3-(methylsulphanyl)prop-2-enoate	Generator
4,4a-Dimethyl-7-oxo-6-(propan-2-ylidene)-decahydronaphthalen-2-yl (2E)-3-(methylsulphanyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₈O₃S

Average Mass

336.4890 Da

Monoisotopic Mass

336.17592 Da

IUPAC Name

4,4a-dimethyl-7-oxo-6-(propan-2-ylidene)-decahydronaphthalen-2-yl (2E)-3-(methylsulfanyl)prop-2-enoate

Traditional Name

4,4a-dimethyl-7-oxo-6-(propan-2-ylidene)-hexahydro-1H-naphthalen-2-yl (2E)-3-(methylsulfanyl)prop-2-enoate

CAS Registry Number

36031-35-3

SMILES

CS\C=C\C(=O)OC1CC(C)C2(C)CC(=C(C)C)C(=O)CC2C1

InChI Identifier

InChI=1S/C19H28O3S/c1-12(2)16-11-19(4)13(3)8-15(9-14(19)10-17(16)20)22-18(21)6-7-23-5/h6-7,13-15H,8-11H2,1-5H3/b7-6+

InChI Key

HDHDUJDLKYTRAS-VOTSOKGWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petasites japonicus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Vinylogous thioester
Enoate ester
Acrylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Thioenolether
Cyclic ketone
Sulfenyl compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organosulfur compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.02	ALOGPS
logP	4.43	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.42 m³·mol⁻¹	ChemAxon
Polarizability	38.15 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

HMDB0035802

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014554

KNApSAcK ID

C00017015

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

131751866

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for S-Japonin (NP0048330)

MOL for NP0048330 (S-Japonin)

3D MOL for NP0048330 (S-Japonin)

3D SDF for NP0048330 (S-Japonin)

3D-SDF for NP0048330 (S-Japonin)

PDB for NP0048330 (S-Japonin)

3D PDB for NP0048330 (S-Japonin)

SMILES for NP0048330 (S-Japonin)

INCHI for NP0048330 (S-Japonin)

Structure for NP0048330 (S-Japonin)

3D Structure for NP0048330 (S-Japonin)