NP-MRD: Showing NP-Card for [(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate (NP0297994)

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Record Information

Version

2.0

Created at

2022-09-10 08:50:57 UTC

Updated at

2022-09-10 08:50:58 UTC

NP-MRD ID

NP0297994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate

Description

[(1R,2S,5S,6R,9S,13R)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-14-en-14-yl]methyl acetate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review very few articles have been published on [(1R,2S,5S,6R,9S,13R)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-14-en-14-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210512D          

 36 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102210512D          

 36 39  0  0  1  0            999 V2000
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    0.6941   -2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057   -2.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601   -3.2889    0.0000 O   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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  1  0  0  0
  6 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
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  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
 14 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0297994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C[C@]23C[C@H]1CCC2[C@]1(C)CC[C@@H](OC(C)=O)[C@](C)(COC(C)=O)C1C[C@@H]3OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O8/c1-16(29)33-14-21-13-28-12-20(21)7-8-22(28)26(5)10-9-24(35-18(3)31)27(6,15-34-17(2)30)23(26)11-25(28)36-19(4)32/h13,20,22-25H,7-12,14-15H2,1-6H3/t20-,22?,23?,24-,25+,26+,27-,28-/m1/s1

> <INCHI_KEY>
VNZPVJZZRDTVIU-YYOMRFRBSA-N

> <FORMULA>
C28H40O8

> <MOLECULAR_WEIGHT>
504.62

> <EXACT_MASS>
504.272318248

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.2740391572774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,5S,6R,9S,13R)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-14-en-14-yl]methyl acetate

> <JCHEM_LOGP>
2.2995416890000007

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.400110432299108

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
129.9053

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,5S,6R,9S,13R)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-14-en-14-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.468   1.405   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.485   0.220   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.021  -1.224   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.967   0.478   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.366  -1.027   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.408   0.107   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.946   1.576   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.911  -0.228   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.166  -4.471   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.693  -4.272   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.284  -2.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.629  -5.495   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.778  -3.515   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.296  -4.965   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.811  -5.242   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.299  -6.139   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   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13   32                                             
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   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   14   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31    8   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2S,5S,6R,9S,13R)-2,6-Bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0,.0,]hexadec-14-en-14-yl]methyl acetic acid	Generator

Chemical Formula

C₂₈H₄₀O₈

Average Mass

504.6200 Da

Monoisotopic Mass

504.27232 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C[C@]23C[C@H]1CCC2[C@]1(C)CC[C@@H](OC(C)=O)[C@](C)(COC(C)=O)C1C[C@@H]3OC(C)=O

InChI Identifier

InChI=1S/C28H40O8/c1-16(29)33-14-21-13-28-12-20(21)7-8-22(28)26(5)10-9-24(35-18(3)31)27(6,15-34-17(2)30)23(26)11-25(28)36-19(4)32/h13,20,22-25H,7-12,14-15H2,1-6H3/t20-,22?,23?,24-,25+,26+,27-,28-/m1/s1

InChI Key

VNZPVJZZRDTVIU-YYOMRFRBSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Steroid
Tetracarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

163076600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate (NP0297994)

MOL for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

3D MOL for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

3D SDF for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

3D-SDF for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

PDB for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

3D PDB for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

SMILES for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

INCHI for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

Structure for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)

3D Structure for NP0297994 ([(1r,2s,5s,6r,9s,13r)-2,6-bis(acetyloxy)-5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-14-yl]methyl acetate)