NP-MRD: Showing NP-Card for (1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate (NP0146210)

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Record Information

Version

2.0

Created at

2022-09-02 01:33:58 UTC

Updated at

2022-09-02 01:33:58 UTC

NP-MRD ID

NP0146210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate

Description

(1R,2R,4R,6R,8S,9Z,11S)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradec-9-en-2-yl (2E)-2-({[(2S)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate is found in Ageratina saltillensis. Based on a literature review very few articles have been published on (1R,2R,4R,6R,8S,9Z,11S)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradec-9-en-2-yl (2E)-2-({[(2S)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203332D          

 34 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022203332D          

 34 36  0  0  1  0            999 V2000
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 27 28  2  0  0  0  0
 29 27  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 34  1  0  0  0  0
 34  2  1  1  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](CO)C(=O)OC\C(=C/C)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@H](O)\C(C)=C/[C@@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O9/c1-6-15(11-26)23(29)31-12-16(7-2)24(30)33-19-10-25(5)20(34-25)9-17(27)13(3)8-18-21(19)14(4)22(28)32-18/h7-8,15,17-21,26-27H,4,6,9-12H2,1-3,5H3/b13-8-,16-7+/t15-,17-,18-,19+,20+,21-,25+/m0/s1

> <INCHI_KEY>
UFMAFPOVVPBPPU-BYBALVMUSA-N

> <FORMULA>
C25H34O9

> <MOLECULAR_WEIGHT>
478.538

> <EXACT_MASS>
478.220282675

> <ALOGPS_LOGP>
1.57

> <ALOGPS_LOGS>
-3.58

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.250   8.844   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.570  10.350   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.977  10.977   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.311  10.207   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.816  12.508   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.310  12.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.540  14.162   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  14.162   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.770  15.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770  12.828   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.540  14.162   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.310  12.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  11.495   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.850  10.161   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.310  10.161   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.310   8.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770  10.161   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000  11.495   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.770  10.161   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.000   8.827   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.540   8.827   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.770   7.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.310   7.494   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.080   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.540   6.160   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.310   4.826   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.540   3.493   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.850   4.826   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.620   3.493   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.160   3.493   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.620   6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.160   6.160   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.540  11.495   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32                                                            
CONECT   34   18    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4R,6R,8S,9Z,11S)-8-Hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0,]tetradec-9-en-2-yl (2E)-2-({[(2S)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₄O₉

Average Mass

478.5380 Da

Monoisotopic Mass

478.22028 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@H](CO)C(=O)OC\C(=C/C)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@H](O)\C(C)=C/[C@@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C25H34O9/c1-6-15(11-26)23(29)31-12-16(7-2)24(30)33-19-10-25(5)20(34-25)9-17(27)13(3)8-18-21(19)14(4)22(28)32-18/h7-8,15,17-21,26-27H,4,6,9-12H2,1-3,5H3/b13-8-,16-7+/t15-,17-,18-,19+,20+,21-,25+/m0/s1

InChI Key

UFMAFPOVVPBPPU-BYBALVMUSA-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
Ageratina saltillensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Primary alcohol
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	1.57	ALOGPS
logS	-3.6	ALOGPS

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

162889587

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,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate (NP0146210)

MOL for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

3D MOL for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

3D SDF for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

3D-SDF for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

PDB for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

3D PDB for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

SMILES for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

INCHI for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

Structure for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)

3D Structure for NP0146210 ((1r,2r,4r,6r,8s,9z,11s)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2e)-2-({[(2s)-2-(hydroxymethyl)butanoyl]oxy}methyl)but-2-enoate)