NP-MRD: Showing NP-Card for 1-O-Acetylkhayanolide A (NP0080371)

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Record Information

Version

2.0

Created at

2022-04-29 01:23:59 UTC

Updated at

2022-04-29 01:24:00 UTC

NP-MRD ID

NP0080371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-O-Acetylkhayanolide A

Description

Methyl (2S)-2-[(1S,2R,5S,6R,10S,12R,13S,15S,16R,18S,19S)-18-(acetyloxy)-6-(furan-3-yl)-15-hydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]Nonadecan-19-yl]-2-hydroxyacetate belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. 1-O-Acetylkhayanolide A is found in Khaya ivorensis and Khaya senegalensis . Based on a literature review very few articles have been published on methyl (2S)-2-[(1S,2R,5S,6R,10S,12R,13S,15S,16R,18S,19S)-18-(acetyloxy)-6-(furan-3-yl)-15-hydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]Nonadecan-19-yl]-2-hydroxyacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203242D          

 40 46  0  0  1  0            999 V2000
    3.2677    2.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7454    2.2959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1864    1.5566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0729    1.5199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5304    2.2356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1098    2.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3880    2.1917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7839    1.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0962   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  5  7  1  0  0  0  0
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  7 12  1  6  0  0  0
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 31 36  1  1  0  0  0
 20 37  1  6  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

     RDKit          3D

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M  END


  Mrv1652304292203242D          

 40 46  0  0  1  0            999 V2000
    3.2677    2.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5987    2.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778    2.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638    3.3205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0126    3.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045    3.3653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5677    0.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -0.9318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  7 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
  5 17  1  6  0  0  0
  4 18  1  6  0  0  0
  3 18  1  1  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  1  0  0  0
 27 28  2  0  0  0  0
 26 29  1  1  0  0  0
 24 30  1  1  0  0  0
 23 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 36  1  1  0  0  0
 20 37  1  6  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>
NP0080371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](O)[C@H]1[C@@]2(C)C[C@]3(OC(C)=O)[C@H](C(=O)[C@H]2O)[C@@]24O[C@]22CC(=O)O[C@@H](C5=COC=C5)[C@]2(C)CC[C@@H]4[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O11/c1-13(30)39-27-12-24(2)19(18(33)23(35)36-5)26(27,4)15-6-8-25(3)22(14-7-9-37-11-14)38-16(31)10-28(25)29(15,40-28)20(27)17(32)21(24)34/h7,9,11,15,18-22,33-34H,6,8,10,12H2,1-5H3/t15-,18+,19+,20+,21-,22+,24-,25+,26-,27+,28+,29-/m1/s1

> <INCHI_KEY>
OQWXSIPGIIEHTO-QYTMJQFDSA-N

> <FORMULA>
C29H34O11

> <MOLECULAR_WEIGHT>
558.58

> <EXACT_MASS>
558.210111915

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.100   5.569   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.125   4.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.948   2.906   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.603   2.837   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.457   4.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.672   5.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.058   4.091   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.797   2.717   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.993   1.392   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.989   0.119   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.469   1.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.881   5.392   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.418   5.491   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.799   6.983   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.498   7.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.312   6.824   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.914   5.713   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.742   1.556   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.713   1.832   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.405   2.621   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.387   3.978   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.217   5.572   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.744   3.458   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.825   1.414   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.586   2.440   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.732   0.013   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.281   0.339   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.276  -1.027   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.596  -1.672   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.153   0.997   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.546   4.701   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.118   4.943   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.385   3.942   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.172   6.198   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.757   6.400   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.755   6.282   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.926   0.951   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.442  -0.213   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.757  -1.739   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.180  -0.183   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4   18   19                                             
CONECT    4    3    5   11   18                                             
CONECT    5    4    6    7   17                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    7   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    5                                                            
CONECT   18    4    3                                                       
CONECT   19    3   20   27                                                  
CONECT   20   19   21   25   37                                             
CONECT   21   20    2   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25   26   30                                             
CONECT   25   24   20                                                       
CONECT   26   24   27   29                                                  
CONECT   27   26   19   28                                                  
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30   24                                                            
CONECT   31   23   32   36                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   31                                                            
CONECT   37   20   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S)-2-[(1S,2R,5S,6R,10S,12R,13S,15S,16R,18S,19S)-18-(acetyloxy)-6-(furan-3-yl)-15-hydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0,.0,.0,.0,]nonadecan-19-yl]-2-hydroxyacetic acid	Generator

Chemical Formula

C₂₉H₃₄O₁₁

Average Mass

558.5800 Da

Monoisotopic Mass

558.21011 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](O)[C@H]1[C@@]2(C)C[C@]3(OC(C)=O)[C@H](C(=O)[C@H]2O)[C@@]24O[C@]22CC(=O)O[C@@H](C5=COC=C5)[C@]2(C)CC[C@@H]4[C@]13C

InChI Identifier

InChI=1S/C29H34O11/c1-13(30)39-27-12-24(2)19(18(33)23(35)36-5)26(27,4)15-6-8-25(3)22(14-7-9-37-11-14)38-16(31)10-28(25)29(15,40-28)20(27)17(32)21(24)34/h7,9,11,15,18-22,33-34H,6,8,10,12H2,1-5H3/t15-,18+,19+,20+,21-,22+,24-,25+,26-,27+,28+,29-/m1/s1

InChI Key

OQWXSIPGIIEHTO-QYTMJQFDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Khaya ivorensis	Plant	KNApSAcK
Khaya senegalensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Tricarboxylic acid or derivatives
Oxepane
Delta_valerolactone
Delta valerolactone
Oxane
Heteroaromatic compound
Methyl ester
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

162925848

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-O-Acetylkhayanolide A (NP0080371)

MOL for NP0080371 (1-O-Acetylkhayanolide A)

3D MOL for NP0080371 (1-O-Acetylkhayanolide A)

3D SDF for NP0080371 (1-O-Acetylkhayanolide A)

3D-SDF for NP0080371 (1-O-Acetylkhayanolide A)

PDB for NP0080371 (1-O-Acetylkhayanolide A)

3D PDB for NP0080371 (1-O-Acetylkhayanolide A)

SMILES for NP0080371 (1-O-Acetylkhayanolide A)

INCHI for NP0080371 (1-O-Acetylkhayanolide A)

Structure for NP0080371 (1-O-Acetylkhayanolide A)

3D Structure for NP0080371 (1-O-Acetylkhayanolide A)