NP-MRD: Showing NP-Card for 2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate (NP0205168)

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Record Information

Version

2.0

Created at

2022-09-05 01:01:16 UTC

Updated at

2022-09-05 01:01:16 UTC

NP-MRD ID

NP0205168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate

Description

CHEMBL3608482 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate is found in Leonurus macranthus. Based on a literature review very few articles have been published on CHEMBL3608482.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203012D          

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M  END

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M  END


  Mrv1652309052203012D          

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    8.3599   -0.9424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4461   -1.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7787   -2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8649   -3.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -1.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6062   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5200    0.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1874    0.6986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3669    0.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 22 17  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 22 37  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0205168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)[C@@H](OC(C)=O)[C@H]2[C@@](C)(COC(C)=O)[C@@H](CC[C@]2(C)[C@@]11CC[C@@](C)(CCOC(C)=O)O1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O10/c1-16-22(33)23(37-20(5)32)24-26(7,15-35-18(3)30)21(36-19(4)31)9-10-27(24,8)28(16)12-11-25(6,38-28)13-14-34-17(2)29/h16,21,23-24H,9-15H2,1-8H3/t16-,21-,23-,24+,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
WJSWULVNRNZNEC-CKSXMQKCSA-N

> <FORMULA>
C28H42O10

> <MOLECULAR_WEIGHT>
538.634

> <EXACT_MASS>
538.277797552

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.90413596124935

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-yl]ethyl acetate

> <JCHEM_LOGP>
1.9855412686666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.195383202747582

> <JCHEM_PKA_STRONGEST_BASIC>
-4.214469994761072

> <JCHEM_POLAR_SURFACE_AREA>
131.50000000000003

> <JCHEM_REFRACTIVITY>
133.13850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolane]-5'-yl]ethyl acetate

> <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       5.976   3.866   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.309   3.096   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.309   1.556   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.643   3.866   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.977   3.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.310   3.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.644   3.096   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.739   1.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.270   4.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.802   4.342   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.122   2.836   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.789   2.066   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.368   3.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.207   5.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.775   3.114   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      19.021   4.020   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.936   1.583   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.343   0.956   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      20.589   1.862   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.428   3.393   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      21.996   1.235   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.690   0.678   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.851  -0.854   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.331  -0.429   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.526  -2.238   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      19.062  -2.345   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      19.737  -3.730   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.274  -3.837   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.876  -5.006   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.605  -1.759   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.766  -3.291   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.520  -4.196   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.681  -5.727   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.113  -3.569   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.198  -1.133   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.037   0.399   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.283   1.304   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.752   1.465   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   37                                             
CONECT   12   11    7                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   37                                                  
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   22   11   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₁₀

Average Mass

538.6340 Da

Monoisotopic Mass

538.27780 Da

IUPAC Name

2-[(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-yl]ethyl acetate

Traditional Name

2-[(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolane]-5'-yl]ethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)[C@@H](OC(C)=O)[C@H]2[C@@](C)(COC(C)=O)[C@@H](CC[C@]2(C)[C@@]11CC[C@@](C)(CCOC(C)=O)O1)OC(C)=O

InChI Identifier

InChI=1S/C28H42O10/c1-16-22(33)23(37-20(5)32)24-26(7,15-35-18(3)30)21(36-19(4)31)9-10-27(24,8)28(16)12-11-25(6,38-28)13-14-34-17(2)29/h16,21,23-24H,9-15H2,1-8H3/t16-,21-,23-,24+,25+,26+,27+,28-/m1/s1

InChI Key

WJSWULVNRNZNEC-CKSXMQKCSA-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
Leonurus macranthus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Grindelane diterpenoid
Tetracarboxylic acid or derivatives
Alpha-acyloxy ketone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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
logP	1.99	ChemAxon
pKa (Strongest Acidic)	16.2	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	133.14 m³·mol⁻¹	ChemAxon
Polarizability	56.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

59002215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122186909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate (NP0205168)

MOL for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

3D MOL for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

3D SDF for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

3D-SDF for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

PDB for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

3D PDB for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

SMILES for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

INCHI for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

Structure for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)

3D Structure for NP0205168 (2-[(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5'-yl]ethyl acetate)