NP-MRD: Showing NP-Card for 8-Hydroxyircinialactam C (NP0331315)

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Record Information

Version

2.0

Created at

2022-12-22 12:53:03 UTC

Updated at

2024-09-03 04:15:19 UTC

NP-MRD ID

NP0331315

Natural Product DOI

https://doi.org/10.57994/0224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Hydroxyircinialactam C

Description

(3S,7E)-14-[1-(carboxymethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-11-hydroxy-3,7,11-trimethyltetradec-7-enoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 8-Hydroxyircinialactam C was first documented in 2018 (PMID: 28888966). Based on a literature review very few articles have been published on (3S,7E)-14-[1-(carboxymethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-11-hydroxy-3,7,11-trimethyltetradec-7-enoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652312222213532D          

 30 30  0  0  1  0            999 V2000
   -5.9845   -7.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3970   -6.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -6.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9681   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -6.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3957   -5.3312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3957   -6.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7477   -4.9187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -6.1562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8095   -5.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1115   -6.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1115   -7.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8260   -8.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8260   -9.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1585   -9.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4135  -10.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2385  -10.3133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7234  -10.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5439  -10.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0288  -11.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8794  -10.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4934   -9.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2780   -9.2737    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  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 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  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END


  Mrv1652312222213532D          

 30 30  0  0  1  0            999 V2000
   -5.9845   -7.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3970   -6.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -6.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9681   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -6.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3957   -5.3312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3957   -6.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7477   -4.9187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -6.1562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8095   -5.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1115   -6.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1115   -7.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8260   -8.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8260   -9.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1585   -9.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4135  -10.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2385  -10.3133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7234  -10.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5439  -10.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0288  -11.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8794  -10.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4934   -9.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2780   -9.2737    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  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 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  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331315

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC\C(C)=C\CCC(C)(O)CCCC1=CCN(CC(O)=O)C1=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H37NO6/c1-17(7-4-8-18(2)15-20(25)26)9-5-12-23(3,30)13-6-10-19-11-14-24(22(19)29)16-21(27)28/h9,11,18,30H,4-8,10,12-16H2,1-3H3,(H,25,26)(H,27,28)/b17-9+/t18-,23?/m0/s1

> <INCHI_KEY>
KUDATKSTLWHADF-VLKWRAORSA-N

> <FORMULA>
C23H37NO6

> <MOLECULAR_WEIGHT>
423.55

> <EXACT_MASS>
423.262087915

$$$$

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  O   UNK     0     -11.171 -13.595   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -11.941 -12.262   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.607 -11.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.607  -9.952   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.274  -9.182   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.940  -9.952   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.940 -11.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.606  -9.182   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.273  -9.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.939  -9.182   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.605  -9.952   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.605 -11.492   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.272  -9.182   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.062  -9.952   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.396  -9.182   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.062 -11.492   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -12.711 -10.928   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.275 -13.032   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.275 -14.572   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.608 -15.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.608 -16.882   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.363 -17.787   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.838 -19.251   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0     -15.378 -19.251   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0     -16.284 -20.497   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.815 -20.336   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -18.720 -21.582   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -18.442 -18.929   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -15.854 -17.787   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -17.319 -17.311   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   18                                             
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                                                            
CONECT   18    2   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   21   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Value	Source
(3S,7E)-14-[1-(Carboxymethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-11-hydroxy-3,7,11-trimethyltetradec-7-enoate	Generator

Chemical Formula

C₂₃H₃₇NO₆

Average Mass

423.5500 Da

Monoisotopic Mass

423.26209 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC\C(C)=C\CCC(C)(O)CCCC1=CCN(CC(O)=O)C1=O)CC(O)=O

InChI Identifier

InChI=1S/C23H37NO6/c1-17(7-4-8-18(2)15-20(25)26)9-5-12-23(3,30)13-6-10-19-11-14-24(22(19)29)16-21(27)28/h9,11,18,30H,4-8,10,12-16H2,1-3H3,(H,25,26)(H,27,28)/b17-9+/t18-,23?/m0/s1

InChI Key

KUDATKSTLWHADF-VLKWRAORSA-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	2024-05-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
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
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
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 (1D, 600 MHz, CD3OD, 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
Sarcotragus sp. (CMB-01012)		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
Alpha-amino acid or derivatives
Methyl-branched fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrroline
Lactam
Carboxamide group
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
Alcohol
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

71048958

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163143836

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Prasad P, Zhang A, Salim AA, Capon RJ: Pursuing sesterterpene lactams in Australian Irciniidae sponges. Fitoterapia. 2018 Apr;126:83-89. doi: 10.1016/j.fitote.2017.09.003. Epub 2017 Sep 6. [PubMed:28888966 ]
DOI: 10.1016/j.fitote.2017.09.003
PMID: 28888966

Showing NP-Card for 8-Hydroxyircinialactam C (NP0331315)

MOL for NP0331315 (8-Hydroxyircinialactam C)

3D MOL for NP0331315 (8-Hydroxyircinialactam C)

3D SDF for NP0331315 (8-Hydroxyircinialactam C)

3D-SDF for NP0331315 (8-Hydroxyircinialactam C)

PDB for NP0331315 (8-Hydroxyircinialactam C)

3D PDB for NP0331315 (8-Hydroxyircinialactam C)

SMILES for NP0331315 (8-Hydroxyircinialactam C)

INCHI for NP0331315 (8-Hydroxyircinialactam C)

Structure for NP0331315 (8-Hydroxyircinialactam C)

3D Structure for NP0331315 (8-Hydroxyircinialactam C)