NP-MRD: Showing NP-Card for 15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate (NP0317642)

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Record Information

Version

2.0

Created at

2022-09-11 17:38:43 UTC

Updated at

2022-09-11 17:38:43 UTC

NP-MRD ID

NP0317642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate

Description

15,17-Bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]Octadec-12-en-9-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate is found in Erythropodium caribaeorum. Based on a literature review very few articles have been published on 15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]Octadec-12-en-9-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112219382D          

 37 40  0  0  0  0            999 V2000
    2.1086    3.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3478    4.5103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7749    1.3685    0.0000 O   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


  Mrv1652309112219382D          

 37 40  0  0  0  0            999 V2000
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  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
  9 36  1  0  0  0  0
 25 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317642

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)OC2C(Cl)C(=C)CC(OC(C)=O)C3OC12C(OC(C)=O)C1C(C)(OC(C)=O)C(=O)C=CC31C

> <INCHI_IDENTIFIER>
InChI=1S/C26H31ClO10/c1-11-10-16(33-13(3)28)20-24(6)9-8-17(31)25(7,36-15(5)30)19(24)22(34-14(4)29)26(37-20)12(2)23(32)35-21(26)18(11)27/h8-9,12,16,18-22H,1,10H2,2-7H3

> <INCHI_KEY>
JAGUWWULEHHAIO-UHFFFAOYSA-N

> <FORMULA>
C26H31ClO10

> <MOLECULAR_WEIGHT>
538.97

> <EXACT_MASS>
538.1605749

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.2951377611546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0^{1,5}.0^{11,16}]octadec-12-en-9-yl acetate

> <JCHEM_LOGP>
2.1090301206666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244477680523606

> <JCHEM_POLAR_SURFACE_AREA>
131.5

> <JCHEM_REFRACTIVITY>
126.3009

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0^{1,5}.0^{11,16}]octadec-12-en-9-yl 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       3.936   6.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.906   5.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.406   5.799   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.764   5.002   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.979   5.948   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.767   7.473   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.340   8.053   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.983   8.419   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.211   3.464   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.046   2.555   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.068   1.542   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.337   0.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.102  -1.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.785   0.198   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.808  -0.992   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.396   1.687   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.713   2.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.172   3.986   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       2.636   4.095   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       7.336   0.447   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.949  -1.043   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.046  -2.124   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.530  -1.714   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.659  -3.614   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.906   0.773   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.018  -0.293   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.776  -1.203   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.699  -1.674   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.843  -2.954   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.523  -4.336   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.306  -2.853   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.497   0.137   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.609  -0.928   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.864   1.633   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.752   2.699   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.273   2.268   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.699   3.748   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17   20                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17    2   19                                                  
CONECT   19   18                                                            
CONECT   20   11   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   36                                                  
CONECT   26   25   27   28   32                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    9   25   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
15,17-Bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0,.0,]octadec-12-en-9-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₁ClO₁₀

Average Mass

538.9700 Da

Monoisotopic Mass

538.16057 Da

IUPAC Name

15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0^{1,5}.0^{11,16}]octadec-12-en-9-yl acetate

Traditional Name

15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0^{1,5}.0^{11,16}]octadec-12-en-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC1C(=O)OC2C(Cl)C(=C)CC(OC(C)=O)C3OC12C(OC(C)=O)C1C(C)(OC(C)=O)C(=O)C=CC31C

InChI Identifier

InChI=1S/C26H31ClO10/c1-11-10-16(33-13(3)28)20-24(6)9-8-17(31)25(7,36-15(5)30)19(24)22(34-14(4)29)26(37-20)12(2)23(32)35-21(26)18(11)27/h8-9,12,16,18-22H,1,10H2,2-7H3

InChI Key

JAGUWWULEHHAIO-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
Erythropodium caribaeorum	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

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tetracarboxylic acid or derivatives
Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
Oxane
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	2.11	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	6	ChemAxon
Refractivity	126.3 m³·mol⁻¹	ChemAxon
Polarizability	52.3 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

73805619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate (NP0317642)

MOL for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

3D MOL for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

3D SDF for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

3D-SDF for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

PDB for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

3D PDB for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

SMILES for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

INCHI for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

Structure for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)

3D Structure for NP0317642 (15,17-bis(acetyloxy)-6-chloro-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-9-yl acetate)