NP-MRD: Showing NP-Card for (2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate (NP0217360)

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Record Information

Version

2.0

Created at

2022-09-05 17:41:13 UTC

Updated at

2022-09-05 17:41:13 UTC

NP-MRD ID

NP0217360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate

Description

(2R,3R,3aR,4S,7S,7aR)-4-{[(2Z)-3-[(R)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-methylbutanoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate is found in Petasites formosanus. Based on a literature review very few articles have been published on (2R,3R,3aR,4S,7S,7aR)-4-{[(2Z)-3-[(R)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219412D          

 32 34  0  0  1  0            999 V2000
    3.4998   -1.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4958    3.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  21   1  23  -1
M  END

     RDKit          3D

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 19 51  1  0
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M  CHG  2  21   1  23  -1
M  END


  Mrv1652309052219412D          

 32 34  0  0  1  0            999 V2000
    3.4998   -1.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6928   -1.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7507    3.0935    0.0000 S   0  3  1  0  0  0  0  0  0  0  0  0
    0.4958    3.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987    2.4804    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2184   -0.6580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  CHG  2  21   1  23  -1
M  END
> <DATABASE_ID>
NP0217360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@@H]1[C@H]2[C@H](CC[C@H](C)[C@@]2(C)C[C@@]11C(=C)COC1=O)OC(=O)\C=C/[S@@+](C)[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O7S/c1-14(2)11-19(26)31-21-20-17(30-18(25)9-10-32(6)28)8-7-15(3)23(20,5)13-24(21)16(4)12-29-22(24)27/h9-10,14-15,17,20-21H,4,7-8,11-13H2,1-3,5-6H3/b10-9-/t15-,17-,20+,21+,23+,24+,32+/m0/s1

> <INCHI_KEY>
UHYZSQIOUDNKRC-AZGMCFRUSA-N

> <FORMULA>
C24H34O7S

> <MOLECULAR_WEIGHT>
466.59

> <EXACT_MASS>
466.202524609

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.34819547905204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3aR,4S,7S,7aR)-7-{[(2Z)-3-[(R)-methanesulfinyl]prop-2-enoyl]oxy}-3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-1-yl 3-methylbutanoate

> <JCHEM_LOGP>
2.3794148356666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.392445224119682

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
120.6644

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,3aR,4S,7S,7aR)-4-{[(2Z)-3-[(R)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.533  -2.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.027  -3.066   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.797  -4.400   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.766  -5.544   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.359  -4.918   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.026  -5.688   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.520  -3.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.014  -3.706   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.244  -2.373   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.339  -3.619   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.262  -2.053   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.293  -3.197   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.738  -0.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.292   0.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.799   0.236   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.829   1.381   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.353   2.845   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.847   3.166   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.384   3.990   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.908   5.454   0.000  0.00  0.00           C+0
HETATM   21  S   UNK     0       1.401   5.775   0.000  0.00  0.00           S+1
HETATM   22  C   UNK     0       0.925   7.239   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.371   4.630   0.000  0.00  0.00           O-1
HETATM   24  C   UNK     0       2.274  -1.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.681  -1.855   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.015  -1.085   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.349  -1.855   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.254  -3.101   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.682  -1.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.016  -1.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.016  -3.395   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.350  -1.085   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8   25                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11   24                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   15    9   25                                                  
CONECT   25   24    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,3AR,4S,7S,7ar)-4-{[(2Z)-3-[(R)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-methylbutanoic acid	Generator
(2R,3R,3AR,4S,7S,7ar)-4-{[(2Z)-3-[(R)-methanesulphinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-methylbutanoate	Generator
(2R,3R,3AR,4S,7S,7ar)-4-{[(2Z)-3-[(R)-methanesulphinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₄H₃₄O₇S

Average Mass

466.5900 Da

Monoisotopic Mass

466.20252 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@@H]1[C@H]2[C@H](CC[C@H](C)[C@@]2(C)C[C@@]11C(=C)COC1=O)OC(=O)\C=C/[S@@+](C)[O-]

InChI Identifier

InChI=1S/C24H34O7S/c1-14(2)11-19(26)31-21-20-17(30-18(25)9-10-32(6)28)8-7-15(3)23(20,5)13-24(21)16(4)12-29-22(24)27/h9-10,14-15,17,20-21H,4,7-8,11-13H2,1-3,5-6H3/b10-9-/t15-,17-,20+,21+,23+,24+,32+/m0/s1

InChI Key

UHYZSQIOUDNKRC-AZGMCFRUSA-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
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
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Acrylic acid or derivatives
Oxolane
Sulfoxide
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Sulfinyl compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organosulfur compound
Organic oxide
Carbonyl group
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

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

9973102

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11798430

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate (NP0217360)

MOL for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

3D MOL for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

3D SDF for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

3D-SDF for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

PDB for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

3D PDB for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

SMILES for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

INCHI for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

Structure for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)

3D Structure for NP0217360 ((2r,3r,3ar,4s,7s,7ar)-4-{[(2z)-3-[(r)-methanesulfinyl]prop-2-enoyl]oxy}-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-3-yl 3-methylbutanoate)