NP-MRD: Showing NP-Card for Ircinialactone A (NP0331313)

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Record Information

Version

2.0

Created at

2022-12-22 12:48:10 UTC

Updated at

2024-09-03 04:15:18 UTC

NP-MRD ID

NP0331313

Natural Product DOI

https://doi.org/10.57994/0222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ircinialactone A

Description

(5Z)-4-hydroxy-3-methyl-5-[(2S,6E,10E)-2,6,10-trimethyl-13-(2-oxo-2,5-dihydrofuran-3-yl)trideca-6,10-dien-1-ylidene]-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Ircinialactone A was first documented in 2018 (PMID: 28888966). Based on a literature review very few articles have been published on (5Z)-4-hydroxy-3-methyl-5-[(2S,6E,10E)-2,6,10-trimethyl-13-(2-oxo-2,5-dihydrofuran-3-yl)trideca-6,10-dien-1-ylidene]-2,5-dihydrofuran-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652312222213482D          

 30 31  0  0  1  0            999 V2000
   -3.6287   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -6.8020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0871   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -5.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341   -5.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690   -5.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -5.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990   -3.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3891   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -3.6275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7721   -8.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -8.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -9.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0778   -8.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5258   -7.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6973   -6.8969    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  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END


  Mrv1652312222213482D          

 30 31  0  0  1  0            999 V2000
   -3.6287   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -6.8020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0871   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -5.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341   -5.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690   -5.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -5.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990   -3.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3891   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -3.6275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7721   -8.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -8.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -9.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0778   -8.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5258   -7.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6973   -6.8969    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  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CCOC1=O)\C=C1/OC(=O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O5/c1-17(8-5-9-18(2)11-7-13-21-14-15-29-25(21)28)10-6-12-19(3)16-22-23(26)20(4)24(27)30-22/h8,11,14,16,19,26H,5-7,9-10,12-13,15H2,1-4H3/b17-8+,18-11+,22-16-/t19-/m0/s1

> <INCHI_KEY>
QTGCSCDBNJDFHL-YLEVQIKZSA-N

> <FORMULA>
C25H34O5

> <MOLECULAR_WEIGHT>
414.542

> <EXACT_MASS>
414.240624195

$$$$

HEADER    PROTEIN                                 22-DEC-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-DEC-22         0                                  
HETATM    1  C   UNK     0      -6.774 -14.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.774 -12.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.440 -11.927   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.106 -12.697   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.772 -11.927   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.439 -12.697   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.439 -14.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.105 -11.927   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.229 -12.697   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.562 -11.927   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896 -12.697   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.896 -14.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.230 -11.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.230 -10.387   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.984  -9.482   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.475  -9.482   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.940  -9.958   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.000  -8.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.905  -6.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.460  -8.017   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.554  -6.771   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.107 -11.927   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.441 -12.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.441 -14.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.775 -15.007   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.936 -16.539   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.442 -16.859   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -13.212 -15.525   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -12.181 -14.381   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -12.502 -12.874   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                                                  
CONECT   15   14   20                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   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   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₅

Average Mass

414.5420 Da

Monoisotopic Mass

414.24062 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=CCOC1=O)\C=C1/OC(=O)C(C)=C1O

InChI Identifier

InChI=1S/C25H34O5/c1-17(8-5-9-18(2)11-7-13-21-14-15-29-25(21)28)10-6-12-19(3)16-22-23(26)20(4)24(27)30-22/h8,11,14,16,19,26H,5-7,9-10,12-13,15H2,1-4H3/b17-8+,18-11+,22-16-/t19-/m0/s1

InChI Key

QTGCSCDBNJDFHL-YLEVQIKZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp. (CMB-01018)		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
Dicarboxylic acid or derivatives
2-furanone
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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

71048962

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163112783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ircinialactone A (NP0331313)

MOL for NP0331313 (Ircinialactone A)

3D MOL for NP0331313 (Ircinialactone A)

3D SDF for NP0331313 (Ircinialactone A)

3D-SDF for NP0331313 (Ircinialactone A)

PDB for NP0331313 (Ircinialactone A)

3D PDB for NP0331313 (Ircinialactone A)

SMILES for NP0331313 (Ircinialactone A)

INCHI for NP0331313 (Ircinialactone A)

Structure for NP0331313 (Ircinialactone A)

3D Structure for NP0331313 (Ircinialactone A)