NP-MRD: Showing NP-Card for Ircinialactam H (NP0331306)

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Record Information

Version

1.0

Created at

2022-12-22 12:27:32 UTC

Updated at

2024-04-19 09:36:22 UTC

NP-MRD ID

NP0331306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ircinialactam H

Description

(3S,7E,11E)-3,7,11-trimethyl-14-[2-oxo-1-(2-phenylethyl)-2,5-dihydro-1H-pyrrol-3-yl]tetradeca-7,11-dienoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. It was first documented in 2023 (PMID: 37078450). Based on a literature review a significant number of articles have been published on (3S,7E,11E)-3,7,11-trimethyl-14-[2-oxo-1-(2-phenylethyl)-2,5-dihydro-1H-pyrrol-3-yl]tetradeca-7,11-dienoic acid (PMID: 37078444) (PMID: 37078443) (PMID: 37078154) (PMID: 37078114).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652312222213272D          

 33 34  0  0  1  0            999 V2000
   -1.6986  -11.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593  -11.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172  -10.8501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0172  -11.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7317  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1606  -10.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462  -11.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1275  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8420  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5564  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6427  -11.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496  -11.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8621  -11.1277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826  -11.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1676  -11.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9880  -11.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4730  -12.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2934  -12.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6290  -11.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441  -10.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3236  -10.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3101  -10.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4816   -9.7076    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  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 23 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END


  Mrv1652312222213272D          

 33 34  0  0  1  0            999 V2000
   -1.6986  -11.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593  -11.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172  -10.8501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0172  -11.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7317  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1606  -10.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462  -11.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1275  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8420  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5564  -10.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6427  -11.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496  -11.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8621  -11.1277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826  -11.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1676  -11.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9880  -11.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4730  -12.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2934  -12.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6290  -11.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441  -10.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3236  -10.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3101  -10.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4816   -9.7076    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  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 23 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CCN(CCC2=CC=CC=C2)C1=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H41NO3/c1-23(12-8-14-25(3)22-28(31)32)10-7-11-24(2)13-9-17-27-19-21-30(29(27)33)20-18-26-15-5-4-6-16-26/h4-6,10,13,15-16,19,25H,7-9,11-12,14,17-18,20-22H2,1-3H3,(H,31,32)/b23-10+,24-13+/t25-/m0/s1

> <INCHI_KEY>
GYIVIVFHMZJYHV-KYFJKOBASA-N

> <FORMULA>
C29H41NO3

> <MOLECULAR_WEIGHT>
451.651

> <EXACT_MASS>
451.308644184

$$$$

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      -3.171 -21.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.171 -20.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.837 -19.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.503 -20.254   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.830 -19.484   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.164 -20.254   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.164 -21.794   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.498 -19.484   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.831 -20.254   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.165 -19.484   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.499 -20.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.499 -21.794   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.832 -19.484   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.166 -20.254   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.500 -19.484   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.166 -21.794   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.504 -19.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.838 -20.254   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.172 -19.484   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.505 -20.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.666 -21.785   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.173 -22.105   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0     -10.943 -20.772   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0     -12.474 -20.611   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.379 -21.857   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.911 -21.696   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -15.816 -22.941   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -17.348 -22.780   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -17.974 -21.374   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.069 -20.128   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -15.537 -20.289   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.912 -19.627   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.232 -18.121   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
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                                                            
CONECT   16   14                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   23   20   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
(3S,7E,11E)-3,7,11-Trimethyl-14-[2-oxo-1-(2-phenylethyl)-2,5-dihydro-1H-pyrrol-3-yl]tetradeca-7,11-dienoate	Generator

Chemical Formula

C₂₉H₄₁NO₃

Average Mass

451.6510 Da

Monoisotopic Mass

451.30864 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=CCN(CCC2=CC=CC=C2)C1=O)CC(O)=O

InChI Identifier

InChI=1S/C29H41NO3/c1-23(12-8-14-25(3)22-28(31)32)10-7-11-24(2)13-9-17-27-19-21-30(29(27)33)20-18-26-15-5-4-6-16-26/h4-6,10,13,15-16,19,25H,7-9,11-12,14,17-18,20-22H2,1-3H3,(H,31,32)/b23-10+,24-13+/t25-/m0/s1

InChI Key

GYIVIVFHMZJYHV-KYFJKOBASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.92 MHz, CD₃OD, 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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Branched fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Pyrroline
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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

71048960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163109183

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Russi AE, Shivakumar P, Luo Z, Bezerra J: Plasticity between ILC2 subsets and amphiregulin expression regulate epithelial repair in biliary atresia. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000418. [PubMed:37078450 ]
Hlady RA, Robertson KD: Epigenetic memory of environmental exposures as a mediator of liver disease. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000414. [PubMed:37078444 ]
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Showing NP-Card for Ircinialactam H (NP0331306)

MOL for NP0331306 (Ircinialactam H)

3D MOL for NP0331306 (Ircinialactam H)

3D SDF for NP0331306 (Ircinialactam H)

3D-SDF for NP0331306 (Ircinialactam H)

PDB for NP0331306 (Ircinialactam H)

3D PDB for NP0331306 (Ircinialactam H)

SMILES for NP0331306 (Ircinialactam H)

INCHI for NP0331306 (Ircinialactam H)

Structure for NP0331306 (Ircinialactam H)

3D Structure for NP0331306 (Ircinialactam H)