NP-MRD: Showing NP-Card for (1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate (NP0319464)

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Record Information

Version

2.0

Created at

2022-09-11 20:30:14 UTC

Updated at

2022-09-11 20:30:14 UTC

NP-MRD ID

NP0319464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate

Description

[(1'S,2R,2'R,7'S,9'S,11'R,12'S)-11'-(acetyloxy)-1'-[(E)-2-[(5S)-5-(acetyloxy)-2-oxo-2,5-dihydrofuran-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]Dodecane]-7'-yl]methyl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate is found in Teucrium asiaticum. Based on a literature review very few articles have been published on [(1'S,2R,2'R,7'S,9'S,11'R,12'S)-11'-(acetyloxy)-1'-[(E)-2-[(5S)-5-(acetyloxy)-2-oxo-2,5-dihydrofuran-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]Dodecane]-7'-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222302D          

 37 41  0  0  1  0            999 V2000
   -1.2541   -2.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112222302D          

 37 41  0  0  1  0            999 V2000
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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  2  0  0  0  0
 16 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  6  0  0  0
 16 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0319464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2O[C@H](OC(C)=O)[C@@]1(\C=C\C1=C[C@@H](OC(C)=O)OC1=O)[C@H]1CCC[C@]3(CO3)[C@]1(COC(C)=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O11/c1-13-20-21(30)26(12-32-14(2)27)18(6-5-8-24(26)11-33-24)25(13,23(37-20)35-16(4)29)9-7-17-10-19(34-15(3)28)36-22(17)31/h7,9-10,13,18-20,23H,5-6,8,11-12H2,1-4H3/b9-7+/t13-,18-,19+,20+,23+,24+,25-,26+/m1/s1

> <INCHI_KEY>
RCPRWFKGQUABHY-KEKAEEHYSA-N

> <FORMULA>
C26H30O11

> <MOLECULAR_WEIGHT>
518.515

> <EXACT_MASS>
518.178811786

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.554879938617546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1'S,2R,2'R,7'S,9'S,11'R,12'S)-11'-(acetyloxy)-1'-[(E)-2-[(5S)-5-(acetyloxy)-2-oxo-2,5-dihydrofuran-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0^{2,7}]dodecane]-7'-yl]methyl acetate

> <JCHEM_LOGP>
1.8467658229999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.06760312106417

> <JCHEM_PKA_STRONGEST_BASIC>
-3.993902956579945

> <JCHEM_POLAR_SURFACE_AREA>
144.03000000000003

> <JCHEM_REFRACTIVITY>
122.91859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,7'S,9'S,11'R,12'S)-11'-(acetyloxy)-1'-[(E)-2-[(5S)-5-(acetyloxy)-2-oxo-5H-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0^{2,7}]dodecane]-7'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.341  -5.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.944  -4.846   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.316  -5.732   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.806  -3.313   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.591  -2.665   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.728  -1.131   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.116  -2.621   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.058  -3.617   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.523  -3.247   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.890  -2.537   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.187  -1.026   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.678  -0.638   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.759  -1.735   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.249  -1.347   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.349  -3.220   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.191   0.148   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.817   1.555   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.349   1.717   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.974   3.124   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.204   4.457   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.234   5.602   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.913   7.108   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.058   8.139   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.737   9.645   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.522   7.664   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.641   4.976   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.481   3.444   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.625   2.414   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.282  -1.633   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.793  -1.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.652   0.102   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.046   1.517   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.483   1.701   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.406   0.468   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.801  -0.948   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.984  -2.477   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.216  -1.553   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31   35                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   29   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27                                                            
CONECT   29   16    9   30                                                  
CONECT   30   29                                                            
CONECT   31   16    6   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    6   36   37                                             
CONECT   36   35   37                                                       
CONECT   37   36   35                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
[(1's,2R,2'r,7's,9's,11'r,12's)-11'-(Acetyloxy)-1'-[(e)-2-[(5S)-5-(acetyloxy)-2-oxo-2,5-dihydrofuran-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0,]dodecane]-7'-yl]methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₀O₁₁

Average Mass

518.5150 Da

Monoisotopic Mass

518.17881 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2O[C@H](OC(C)=O)[C@@]1(\C=C\C1=C[C@@H](OC(C)=O)OC1=O)[C@H]1CCC[C@]3(CO3)[C@]1(COC(C)=O)C2=O

InChI Identifier

InChI=1S/C26H30O11/c1-13-20-21(30)26(12-32-14(2)27)18(6-5-8-24(26)11-33-24)25(13,23(37-20)35-16(4)29)9-7-17-10-19(34-15(3)28)36-22(17)31/h7,9-10,13,18-20,23H,5-6,8,11-12H2,1-4H3/b9-7+/t13-,18-,19+,20+,23+,24+,25-,26+/m1/s1

InChI Key

RCPRWFKGQUABHY-KEKAEEHYSA-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
Teucrium asiaticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Acylal
Oxepane
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Acetal
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen 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

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

163051047

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate (NP0319464)

MOL for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

3D MOL for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

3D SDF for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

3D-SDF for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

PDB for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

3D PDB for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

SMILES for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

INCHI for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

Structure for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)

3D Structure for NP0319464 ((1's,2r,2'r,7's,9's,11'r,12's)-11'-(acetyloxy)-1'-[(1e)-2-[(5s)-5-(acetyloxy)-2-oxo-5h-furan-3-yl]ethenyl]-12'-methyl-8'-oxo-10'-oxaspiro[oxirane-2,6'-tricyclo[7.2.1.0²,⁷]dodecan]-7'-ylmethyl acetate)