NP-MRD: Showing NP-Card for (1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate (NP0215515)

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Record Information

Version

2.0

Created at

2022-09-05 15:09:38 UTC

Updated at

2022-09-05 15:09:39 UTC

NP-MRD ID

NP0215515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate

Description

Excavatolide G belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate is found in Briareum excavatum. Based on a literature review very few articles have been published on Excavatolide G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217092D          

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M  END

     RDKit          2D

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M  END


  Mrv1652309052217092D          

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    2.0530    1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856    0.9503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4805    1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429    2.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.6638    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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 29 28  1  1  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 12 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0215515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](C[C@H](OC(C)=O)[C@@]2(C)[C@H]1[C@@H](OC(C)=O)[C@@]13O[C@@]1(C)C(=O)O[C@H]3\C=C(C)/CC[C@H]2OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O11/c1-13-9-10-20(35-16(4)30)26(7)21(36-17(5)31)12-19(34-15(3)29)14(2)23(26)24(37-18(6)32)28-22(11-13)38-25(33)27(28,8)39-28/h11,14,19-24H,9-10,12H2,1-8H3/b13-11-/t14-,19-,20+,21-,22-,23+,24+,26-,27-,28+/m0/s1

> <INCHI_KEY>
WRYYYJGXEFMEDX-JJARENSVSA-N

> <FORMULA>
C28H38O11

> <MOLECULAR_WEIGHT>
550.601

> <EXACT_MASS>
550.241412044

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
45.35794705348102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4R,5S,7S,8S,9R,12Z,14S,17R)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-12-en-2-yl acetate

> <JCHEM_LOGP>
1.7148451353333316

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.360153768398971

> <JCHEM_POLAR_SURFACE_AREA>
144.03

> <JCHEM_REFRACTIVITY>
131.99949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4R,5S,7S,8S,9R,12Z,14S,17R)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-12-en-2-yl 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       6.918  -6.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.848  -5.088   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.145  -4.258   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.481  -4.380   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.410  -2.841   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.708  -2.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.637  -0.473   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.935   0.357   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.302  -0.351   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.599   0.479   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.372  -1.890   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.270   0.236   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.567   1.066   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.973  -0.594   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.043  -2.133   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.746  -2.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.605   0.114   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.147  -1.327   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.170  -2.518   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.712  -3.959   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.504  -2.427   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.308  -0.716   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.498  -1.693   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.057  -2.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.445  -3.726   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.466  -2.466   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.174  -3.833   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.156  -1.089   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.059  -0.008   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.129   1.531   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.168   2.361   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.098   3.899   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.535   1.652   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.832   2.482   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.200   1.774   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.497   2.604   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.427   4.142   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.059   4.851   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.724   4.972   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   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14   35                                             
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24   29                                             
CONECT   23   22   24                                                       
CONECT   24   23   22   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   12   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₁₁

Average Mass

550.6010 Da

Monoisotopic Mass

550.24141 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](C[C@H](OC(C)=O)[C@@]2(C)[C@H]1[C@@H](OC(C)=O)[C@@]13O[C@@]1(C)C(=O)O[C@H]3\C=C(C)/CC[C@H]2OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C28H38O11/c1-13-9-10-20(35-16(4)30)26(7)21(36-17(5)31)12-19(34-15(3)29)14(2)23(26)24(37-18(6)32)28-22(11-13)38-25(33)27(28,8)39-28/h11,14,19-24H,9-10,12H2,1-8H3/b13-11-/t14-,19-,20+,21-,22-,23+,24+,26-,27-,28+/m0/s1

InChI Key

WRYYYJGXEFMEDX-JJARENSVSA-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
Briareum excavatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Briarane diterpenoid
Diterpenoid
Diterpene lactone
Pentacarboxylic acid or derivatives
Gamma butyrolactone
Para-dioxane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049373

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

100967685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate (NP0215515)

MOL for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

3D MOL for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

3D SDF for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

3D-SDF for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

PDB for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

3D PDB for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

SMILES for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

INCHI for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

Structure for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)

3D Structure for NP0215515 ((1r,2r,3s,4r,5s,7s,8s,9r,12z,14s,17r)-5,7,9-tris(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-2-yl acetate)