NP-MRD: Showing NP-Card for 2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate (NP0144499)

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Record Information

Version

2.0

Created at

2022-09-01 23:29:14 UTC

Updated at

2022-09-01 23:29:14 UTC

NP-MRD ID

NP0144499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate

Description

7,9,10-Tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]Octadecan-2-yl acetate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate is found in Dichotella gemmacea, Junceella fragilis and Junceella juncea. 7,9,10-Tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]Octadecan-2-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520222D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171520222D          

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    4.9515    0.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2363    1.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    2.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050    2.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5294    2.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209    1.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    2.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645    2.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    3.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
 11 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)OC2C(Cl)C(=C)C3OC12C(OC(C)=O)C1C(=C)CCC(OC(C)=O)C1(C)C(OC(C)=O)C3OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H35ClO11/c1-11-9-10-18(35-14(4)30)27(8)19(11)23(37-16(6)32)28-13(3)26(34)39-24(28)20(29)12(2)21(40-28)22(36-15(5)31)25(27)38-17(7)33/h13,18-25H,1-2,9-10H2,3-8H3

> <INCHI_KEY>
PXWWTSQKNXBHTK-UHFFFAOYSA-N

> <FORMULA>
C28H35ClO11

> <MOLECULAR_WEIGHT>
583.03

> <EXACT_MASS>
582.1867896

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.56785899769452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,9,10-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-2-yl acetate

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
1.9178591456666667

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.276210785177488

> <JCHEM_POLAR_SURFACE_AREA>
140.73000000000002

> <JCHEM_REFRACTIVITY>
134.6601

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
junceellin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.260  -3.008   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.967  -1.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.443  -1.950   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.804  -3.352   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.687  -0.611   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.763   0.508   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.299   2.043   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       0.811   2.443   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       3.448   3.120   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.066   4.612   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.001   2.722   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.740   1.273   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.307  -0.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.770  -0.874   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.501  -2.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.053  -2.915   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.784  -4.432   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.746  -3.730   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.346  -0.629   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.007  -2.020   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.134  -3.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.542  -2.142   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.416  -0.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.755   0.517   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.629   1.785   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.164   1.662   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.038   2.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.825   0.271   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.220   0.639   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.243   1.791   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.908   2.198   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.176   3.072   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.053   4.607   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.663   5.268   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.322   5.480   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.572   3.039   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.851   4.553   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.678   5.552   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.227   5.035   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.956   7.066   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12    2    6   14                                             
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   29                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   19   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   11   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
7,9,10-Tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0,.0,]octadecan-2-yl acetic acid	Generator
7,9,10-Tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-2-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₅ClO₁₁

Average Mass

583.0300 Da

Monoisotopic Mass

582.18679 Da

IUPAC Name

7,9,10-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-2-yl acetate

Traditional Name

junceellin

CAS Registry Number

Not Available

SMILES

CC1C(=O)OC2C(Cl)C(=C)C3OC12C(OC(C)=O)C1C(=C)CCC(OC(C)=O)C1(C)C(OC(C)=O)C3OC(C)=O

InChI Identifier

InChI=1S/C28H35ClO11/c1-11-9-10-18(35-14(4)30)27(8)19(11)23(37-16(6)32)28-13(3)26(34)39-24(28)20(29)12(2)21(40-28)22(36-15(5)31)25(27)38-17(7)33/h13,18-25H,1-2,9-10H2,3-8H3

InChI Key

PXWWTSQKNXBHTK-UHFFFAOYSA-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
Dichotella gemmacea	LOTUS Database	35616633
Junceella fragilis	LOTUS Database	35616633
Junceella juncea	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Furopyran
Gamma butyrolactone
Pyran
Oxane
Furan
Tetrahydrofuran
Carboxylic acid ester
Lactone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alkyl halide
Hydrocarbon derivative
Organic oxide
Alkyl chloride
Organic oxygen compound
Carbonyl group
Organohalogen compound
Organochloride
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
logP	2.83	ALOGPS
logP	1.92	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	140.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.66 m³·mol⁻¹	ChemAxon
Polarizability	56.57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

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

14264083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate (NP0144499)

MOL for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

3D MOL for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

3D SDF for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

3D-SDF for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

PDB for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

3D PDB for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

SMILES for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

INCHI for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

Structure for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)

3D Structure for NP0144499 (2,7,9-tris(acetyloxy)-13-chloro-8,17-dimethyl-4,12-dimethylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan-10-yl acetate)