NP-MRD: Showing NP-Card for Cacolide H (NP0331166)

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Record Information

Version

1.0

Created at

2022-11-21 17:58:00 UTC

Updated at

2024-04-19 09:31:51 UTC

NP-MRD ID

NP0331166

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cacolide H

Description

2-{4-[(3E,7E,12R)-12-[(2-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)methyl]-4,8-dimethyltrideca-3,7-dien-1-yl]-2-oxo-2,5-dihydro-1H-pyrrol-1-yl}acetic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on 2-{4-[(3E,7E,12R)-12-[(2-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)methyl]-4,8-dimethyltrideca-3,7-dien-1-yl]-2-oxo-2,5-dihydro-1H-pyrrol-1-yl}acetic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311212218582D          

 34 35  0  0  1  0            999 V2000
   -3.7212   -7.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8633   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8633   -7.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -7.0429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9946   -7.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7091   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -7.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -6.2893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -7.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235   -8.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -9.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8756   -8.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8646   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5791   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -7.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4723   -8.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8848   -7.3205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7052   -7.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0408   -6.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8613   -6.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5559   -5.8131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3327   -6.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8078   -8.7886    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 22  2  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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 25 33  1  0  0  0  0
 27 34  2  0  0  0  0
M  END


  Mrv1652311212218582D          

 34 35  0  0  1  0            999 V2000
   -3.7212   -7.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8633   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8633   -7.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -7.0429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9946   -7.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7091   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -7.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -6.2893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -7.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235   -8.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -9.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8756   -8.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8646   -6.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5791   -7.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -7.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4723   -8.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8848   -7.3205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7052   -7.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0408   -6.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8613   -6.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5559   -5.8131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3327   -6.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8078   -8.7886    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 22  2  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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 25 33  1  0  0  0  0
 27 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331166

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CC(=O)N(CC(O)=O)C1)CC1(O)OC(=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO6/c1-19(10-6-12-21(3)15-27(33)16-22(4)26(32)34-27)8-5-9-20(2)11-7-13-23-14-24(29)28(17-23)18-25(30)31/h8,11,14,16,21,33H,5-7,9-10,12-13,15,17-18H2,1-4H3,(H,30,31)/b19-8+,20-11+/t21-,27?/m1/s1

> <INCHI_KEY>
TWNIZAVLGTZDSY-KNUZUNNPSA-N

> <FORMULA>
C27H39NO6

> <MOLECULAR_WEIGHT>
473.61

> <EXACT_MASS>
473.27773798

$$$$

HEADER    PROTEIN                                 21-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-22         0                                  
HETATM    1  C   UNK     0      -6.946 -14.687   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.946 -13.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.613 -12.377   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.279 -13.147   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.945 -12.377   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.611 -13.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.611 -14.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.278 -12.377   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.056 -13.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.390 -12.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.723 -13.147   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.723 -14.687   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.057 -12.377   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.391 -13.147   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.855 -13.623   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.017 -11.740   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.485 -14.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.391 -15.639   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.915 -17.103   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.855 -15.163   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.101 -16.068   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.280 -12.377   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.614 -13.147   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.947 -12.377   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.281 -13.147   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.442 -14.678   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.948 -14.999   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0     -14.718 -13.665   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0     -16.250 -13.504   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.876 -12.097   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -18.408 -11.936   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -15.971 -10.851   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -13.688 -12.520   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -14.575 -16.405   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14   20                                                       
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   15   21                                                  
CONECT   21   20                                                            
CONECT   22    2   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   25                                                       
CONECT   34   27                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-{4-[(3E,7E,12R)-12-[(2-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)methyl]-4,8-dimethyltrideca-3,7-dien-1-yl]-2-oxo-2,5-dihydro-1H-pyrrol-1-yl}acetate	Generator

Chemical Formula

C₂₇H₃₉NO₆

Average Mass

473.6100 Da

Monoisotopic Mass

473.27774 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CC(=O)N(CC(O)=O)C1)CC1(O)OC(=O)C(C)=C1

InChI Identifier

InChI=1S/C27H39NO6/c1-19(10-6-12-21(3)15-27(33)16-22(4)26(32)34-27)8-5-9-20(2)11-7-13-23-14-24(29)28(17-23)18-25(30)31/h8,11,14,16,21,33H,5-7,9-10,12-13,15,17-18H2,1-4H3,(H,30,31)/b19-8+,20-11+/t21-,27?/m1/s1

InChI Key

TWNIZAVLGTZDSY-KNUZUNNPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Diterpenoid
Diterpene lactone
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Pyrroline
Dihydrofuran
Lactone
Lactam
Hemiacetal
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

70999835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163113790

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cacolide H (NP0331166)

MOL for NP0331166 (Cacolide H)

3D MOL for NP0331166 (Cacolide H)

3D SDF for NP0331166 (Cacolide H)

3D-SDF for NP0331166 (Cacolide H)

PDB for NP0331166 (Cacolide H)

3D PDB for NP0331166 (Cacolide H)

SMILES for NP0331166 (Cacolide H)

INCHI for NP0331166 (Cacolide H)

Structure for NP0331166 (Cacolide H)

3D Structure for NP0331166 (Cacolide H)