NP-MRD: Showing NP-Card for Ircinialactam A (NP0331314)

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Record Information

Version

1.0

Created at

2022-12-22 12:50:36 UTC

Updated at

2024-04-19 09:36:35 UTC

NP-MRD ID

NP0331314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ircinialactam A

Description

2-{3-[(3E,7E,12S)-12-{[(2Z)-3-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]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-{3-[(3E,7E,12S)-12-{[(2Z)-3-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]methyl}-4,8-dimethyltrideca-3,7-dien-1-yl]-2-oxo-2,5-dihydro-1H-pyrrol-1-yl}acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215512D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052215512D          

 34 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0331314

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO6/c1-18(10-6-12-20(3)16-23-25(31)21(4)27(33)34-23)8-5-9-19(2)11-7-13-22-14-15-28(26(22)32)17-24(29)30/h8,11,14,16,20,31H,5-7,9-10,12-13,15,17H2,1-4H3,(H,29,30)/b18-8+,19-11+,23-16-/t20-/m0/s1

> <INCHI_KEY>
BIQICBSXLAWWPY-CHVWLSOJSA-N

> <FORMULA>
C27H37NO6

> <MOLECULAR_WEIGHT>
471.594

> <EXACT_MASS>
471.262087915

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.363886058242784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{3-[(3E,7E,12S)-13-[(2Z)-3-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]-4,8,12-trimethyltrideca-3,7-dien-1-yl]-2-oxo-2,5-dihydro-1H-pyrrol-1-yl}acetic acid

> <JCHEM_LOGP>
4.571350583999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.070923003319737

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7858891710705183

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4324814362138213

> <JCHEM_POLAR_SURFACE_AREA>
104.14000000000001

> <JCHEM_REFRACTIVITY>
136.02220000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{3-[(3E,7E,12S)-13-[(2Z)-3-hydroxy-4-methyl-5-oxofuran-2-ylidene]-4,8,12-trimethyltrideca-3,7-dien-1-yl]-2-oxo-5H-pyrrol-1-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.175 -20.142   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.270 -18.896   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.746 -17.431   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.210 -16.955   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.500 -16.526   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.500 -14.986   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.166 -14.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.166 -12.676   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.832 -14.986   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.501 -14.216   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.835 -14.986   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.169 -14.216   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.169 -12.676   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.502 -14.986   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.836 -14.216   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.170 -14.986   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.503 -14.216   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.503 -12.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.837 -14.986   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.171 -14.216   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.504 -14.986   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.838 -14.216   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.999 -12.684   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.505 -12.364   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      16.275 -13.698   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      17.807 -13.859   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.433 -15.266   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      19.965 -15.427   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      17.528 -16.512   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.245 -14.842   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.565 -16.349   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.254 -17.431   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.730 -18.896   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.825 -20.142   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   22   31                                                  
CONECT   31   30                                                            
CONECT   32    5   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₇H₃₇NO₆

Average Mass

471.5940 Da

Monoisotopic Mass

471.26209 Da

IUPAC Name

2-{3-[(3E,7E,12S)-13-[(2Z)-3-hydroxy-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]-4,8,12-trimethyltrideca-3,7-dien-1-yl]-2-oxo-2,5-dihydro-1H-pyrrol-1-yl}acetic acid

Traditional Name

{3-[(3E,7E,12S)-13-[(2Z)-3-hydroxy-4-methyl-5-oxofuran-2-ylidene]-4,8,12-trimethyltrideca-3,7-dien-1-yl]-2-oxo-5H-pyrrol-1-yl}acetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CCN(CC(O)=O)C1=O)\C=C1/OC(=O)C(C)=C1O

InChI Identifier

InChI=1S/C27H37NO6/c1-18(10-6-12-20(3)16-23-25(31)21(4)27(33)34-23)8-5-9-19(2)11-7-13-22-14-15-28(26(22)32)17-24(29)30/h8,11,14,16,20,31H,5-7,9-10,12-13,15,17H2,1-4H3,(H,29,30)/b18-8+,19-11+,23-16-/t20-/m0/s1

InChI Key

BIQICBSXLAWWPY-CHVWLSOJSA-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
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	¹³C NMR Spectrum (1D, 150.92 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Diterpene lactone
Diterpenoid
Alpha-amino acid or derivatives
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Enol ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Pyrroline
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Enol
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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
logP	4.57	ChemAxon
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-0.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.14 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	136.02 m³·mol⁻¹	ChemAxon
Polarizability	54.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

24668725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54726844

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ircinialactam A (NP0331314)

MOL for NP0331314 (Ircinialactam A)

3D MOL for NP0331314 (Ircinialactam A)

3D SDF for NP0331314 (Ircinialactam A)

3D-SDF for NP0331314 (Ircinialactam A)

PDB for NP0331314 (Ircinialactam A)

3D PDB for NP0331314 (Ircinialactam A)

SMILES for NP0331314 (Ircinialactam A)

INCHI for NP0331314 (Ircinialactam A)

Structure for NP0331314 (Ircinialactam A)

3D Structure for NP0331314 (Ircinialactam A)