NP-MRD: Showing NP-Card for 4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate (NP0217709)

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Record Information

Version

2.0

Created at

2022-09-05 18:08:40 UTC

Updated at

2022-09-05 18:08:40 UTC

NP-MRD ID

NP0217709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate

Description

4-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate is found in Petasites formosanus. 4-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171504372D          

 28 30  0  0  0  0            999 V2000
    5.1973    1.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452    1.3779    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9002    0.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3481   -0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412    0.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862    0.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891   -0.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -1.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576   -2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -2.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -3.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425   -3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -2.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7592   -1.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -2.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -3.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -1.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -1.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -0.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -0.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1721   -0.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.9740    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
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END


  Mrv1533004171504372D          

 28 30  0  0  0  0            999 V2000
    5.1973    1.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452    1.3779    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9002    0.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3481   -0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412    0.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862    0.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891   -0.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -1.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576   -2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -2.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -3.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425   -3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -2.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7592   -1.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -2.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -3.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -1.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -1.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -0.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432   -0.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1721   -0.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.9740    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
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC=CC(=O)OC1C2C(CCC(C)C2(C)CC11C(=C)COC1=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O6S/c1-12-6-7-15(26-14(3)22)17-18(27-16(23)8-9-28-5)21(11-20(12,17)4)13(2)10-25-19(21)24/h8-9,12,15,17-18H,2,6-7,10-11H2,1,3-5H3

> <INCHI_KEY>
VWLQTJPASTUQRU-UHFFFAOYSA-N

> <FORMULA>
C21H28O6S

> <MOLECULAR_WEIGHT>
408.51

> <EXACT_MASS>
408.160659796

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.581007406942334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoate

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.9630240479999994

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.513639994597131

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
105.28519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoate

> <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       9.702   3.716   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       8.671   2.572   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       9.147   1.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.117  -0.037   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.610   0.283   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.134   1.748   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.580  -0.861   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.056  -2.326   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.520  -2.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.854  -2.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.188  -2.802   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.188  -4.342   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.854  -5.112   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.854  -6.652   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.520  -4.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.359  -5.873   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.056  -4.818   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.150  -3.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.245  -4.818   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.721  -6.282   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.781  -4.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.781  -2.802   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.245  -2.326   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.721  -0.861   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.854  -0.492   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.188   0.278   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.521  -0.492   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.188   1.818   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   18                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    8   19   23                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   10   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
4-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoic acid	Generator
4-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulphanyl)prop-2-enoate	Generator
4-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulphanyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₁H₂₈O₆S

Average Mass

408.5100 Da

Monoisotopic Mass

408.16066 Da

IUPAC Name

4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoate

Traditional Name

4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl 3-(methylsulfanyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CSC=CC(=O)OC1C2C(CCC(C)C2(C)CC11C(=C)COC1=O)OC(C)=O

InChI Identifier

InChI=1S/C21H28O6S/c1-12-6-7-15(26-14(3)22)17-18(27-16(23)8-9-28-5)21(11-20(12,17)4)13(2)10-25-19(21)24/h8-9,12,15,17-18H,2,6-7,10-11H2,1,3-5H3

InChI Key

VWLQTJPASTUQRU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petasites formosanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Vinylogous thioester
Acrylic acid or derivatives
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Thioenolether
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Sulfenyl compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
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	3.17	ALOGPS
logP	2.96	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.29 m³·mol⁻¹	ChemAxon
Polarizability	42.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

85243045

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate (NP0217709)

MOL for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

3D MOL for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

3D SDF for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

3D-SDF for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

PDB for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

3D PDB for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

SMILES for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

INCHI for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

Structure for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)

3D Structure for NP0217709 (4-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-(methylsulfanyl)prop-2-enoate)