NP-MRD: Showing NP-Card for (1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate (NP0301319)

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Record Information

Version

2.0

Created at

2022-09-10 14:11:30 UTC

Updated at

2022-09-10 14:11:31 UTC

NP-MRD ID

NP0301319

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate

Description

Erythrolide F belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate is found in Erythropodium caribaeorum. Based on a literature review very few articles have been published on Erythrolide F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102216112D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102216112D          

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 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 26 17  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
  6 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0301319

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)C[C@@H](O)[C@H]3O[C@]12[C@H](OC(=O)COC(C)=O)[C@@H]1[C@]3(C)C=CC(=O)[C@@]1(C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31ClO11/c1-11-9-15(30)20-24(5)8-7-16(31)25(6,37-14(4)29)19(24)22(35-17(32)10-34-13(3)28)26(38-20)12(2)23(33)36-21(26)18(11)27/h7-8,12,15,18-22,30H,1,9-10H2,2-6H3/t12-,15+,18-,19+,20+,21-,22+,24-,25+,26+/m0/s1

> <INCHI_KEY>
SRNKBZPZPHQSTQ-SCAWABMISA-N

> <FORMULA>
C26H31ClO11

> <MOLECULAR_WEIGHT>
554.97

> <EXACT_MASS>
554.1554895

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.03108913896106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,6S,9R,10S,11S,15S,16S,17R)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0^{1,5}.0^{11,16}]octadec-12-en-17-yl 2-(acetyloxy)acetate

> <JCHEM_LOGP>
1.2917820746666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.100108743272344

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1924124356926757

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
128.00310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6S,9R,10S,11S,15S,16S,17R)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0^{1,5}.0^{11,16}]octadec-12-en-17-yl (acetyloxy)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      -3.111   3.511   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.699   4.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.714   5.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.584   6.784   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.172   8.207   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.018   6.805   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.584   5.441   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.300   4.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.492   3.141   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.984   3.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.988   1.670   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.874   0.411   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.449   1.691   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.031   3.173   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.561   3.052   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -1.075   1.600   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       3.693   5.159   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.026   4.389   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.360   5.159   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.360   6.699   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.694   4.389   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.027   5.159   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.361   4.389   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.695   5.159   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.361   2.849   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.797   6.759   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.120   7.547   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.667   6.107   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.633   7.835   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.639   6.669   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.152   6.957   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.132   5.215   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.099   9.087   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.422   9.875   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.755   9.839   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.432   9.051   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.453   7.511   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.140   8.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14   17                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17    8   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17   27   37                                                  
CONECT   27   26   28   29   33                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    6   26   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁ClO₁₁

Average Mass

554.9700 Da

Monoisotopic Mass

554.15549 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)C[C@@H](O)[C@H]3O[C@]12[C@H](OC(=O)COC(C)=O)[C@@H]1[C@]3(C)C=CC(=O)[C@@]1(C)OC(C)=O

InChI Identifier

InChI=1S/C26H31ClO11/c1-11-9-15(30)20-24(5)8-7-16(31)25(6,37-14(4)29)19(24)22(35-17(32)10-34-13(3)28)26(38-20)12(2)23(33)36-21(26)18(11)27/h7-8,12,15,18-22,30H,1,9-10H2,2-6H3/t12-,15+,18-,19+,20+,21-,22+,24-,25+,26+/m0/s1

InChI Key

SRNKBZPZPHQSTQ-SCAWABMISA-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
Cyclic ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Alkyl halide
Carbonyl group
Organooxygen compound
Organohalogen compound
Organochloride
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	1.29	ChemAxon
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128 m³·mol⁻¹	ChemAxon
Polarizability	53.03 Å³	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045304

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

101603384

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate (NP0301319)

MOL for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

3D MOL for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

3D SDF for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

3D-SDF for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

PDB for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

3D PDB for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

SMILES for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

INCHI for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

Structure for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)

3D Structure for NP0301319 ((1s,2r,5r,6s,9r,10s,11s,15s,16s,17r)-15-(acetyloxy)-6-chloro-9-hydroxy-2,11,15-trimethyl-7-methylidene-3,14-dioxo-4,18-dioxatetracyclo[8.7.1.0¹,⁵.0¹¹,¹⁶]octadec-12-en-17-yl 2-(acetyloxy)acetate)