NP-MRD: Showing NP-Card for n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid (NP0181557)

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Record Information

Version

2.0

Created at

2022-09-03 20:05:49 UTC

Updated at

2022-09-03 20:05:49 UTC

NP-MRD ID

NP0181557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid

Description

N-[2-hydroxy-3,4,7-trimethyl-5,8-dioxo-6-(propan-2-yl)-1,4,7-triazacyclotridec-1-en-9-yl]octa-2,4,6-trienimidic acid belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid is found in Aspergillus sclerotiorum. N-[2-hydroxy-3,4,7-trimethyl-5,8-dioxo-6-(propan-2-yl)-1,4,7-triazacyclotridec-1-en-9-yl]octa-2,4,6-trienimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512542D          

 32 32  0  0  0  0            999 V2000
    3.7573    6.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    5.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982    5.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    4.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2391    3.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153    2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801    2.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    2.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926    3.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335    1.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097    0.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    1.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2423    1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4121   -0.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -1.2765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5209   -1.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968   -1.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -2.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8727   -1.8933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -2.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -1.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299   -1.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398   -0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0827    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125    1.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
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 12 13  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251512542D          

 32 32  0  0  0  0            999 V2000
    3.7573    6.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    5.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0181557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC=CC=CC(=O)NC1CCCCNC(=O)C(C)N(C)C(=O)C(C(C)C)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H38N4O4/c1-7-8-9-10-11-15-20(29)26-19-14-12-13-16-25-22(30)18(4)27(5)24(32)21(17(2)3)28(6)23(19)31/h7-11,15,17-19,21H,12-14,16H2,1-6H3,(H,25,30)(H,26,29)

> <INCHI_KEY>
WTFVTPDZPCKVCO-UHFFFAOYSA-N

> <FORMULA>
C24H38N4O4

> <MOLECULAR_WEIGHT>
446.592

> <EXACT_MASS>
446.28930572

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.443525660601445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[3,4,7-trimethyl-2,5,8-trioxo-6-(propan-2-yl)-1,4,7-triazacyclotridecan-9-yl]octa-2,4,6-trienamide

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
1.6095956236666664

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.310226802649765

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.544625045171731

> <JCHEM_PKA_STRONGEST_BASIC>
-0.41547595142527494

> <JCHEM_POLAR_SURFACE_AREA>
98.82

> <JCHEM_REFRACTIVITY>
128.39559999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(6-isopropyl-3,4,7-trimethyl-2,5,8-trioxo-1,4,7-triazacyclotridecan-9-yl)octa-2,4,6-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       7.014  12.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.529  10.551   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.530   9.379   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.045   7.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.046   6.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.562   5.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.563   4.133   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.048   4.412   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.533   5.863   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       3.049   3.240   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.565   1.789   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.756   2.764   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.052   1.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.662   0.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.369  -1.087   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.537  -2.383   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.999  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.706  -3.679   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.167  -3.607   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.874  -4.975   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.629  -3.534   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.797  -4.830   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.923  -2.166   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.616  -2.094   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.754  -0.870   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.216  -0.798   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.491   0.571   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.219  -1.357   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       1.048   0.499   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -0.154   1.461   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.879   1.795   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.143   3.147   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   11   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
N-[2-Hydroxy-3,4,7-trimethyl-5,8-dioxo-6-(propan-2-yl)-1,4,7-triazacyclotridec-1-en-9-yl]octa-2,4,6-trienimidate	Generator

Chemical Formula

C₂₄H₃₈N₄O₄

Average Mass

446.5920 Da

Monoisotopic Mass

446.28931 Da

IUPAC Name

N-[3,4,7-trimethyl-2,5,8-trioxo-6-(propan-2-yl)-1,4,7-triazacyclotridecan-9-yl]octa-2,4,6-trienamide

Traditional Name

N-(6-isopropyl-3,4,7-trimethyl-2,5,8-trioxo-1,4,7-triazacyclotridecan-9-yl)octa-2,4,6-trienamide

CAS Registry Number

Not Available

SMILES

CC=CC=CC=CC(=O)NC1CCCCNC(=O)C(C)N(C)C(=O)C(C(C)C)N(C)C1=O

InChI Identifier

InChI=1S/C24H38N4O4/c1-7-8-9-10-11-15-20(29)26-19-14-12-13-16-25-22(30)18(4)27(5)24(32)21(17(2)3)28(6)23(19)31/h7-11,15,17-19,21H,12-14,16H2,1-6H3,(H,25,30)(H,26,29)

InChI Key

WTFVTPDZPCKVCO-UHFFFAOYSA-N

Experimental Spectra

Not Available

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

Species Name	Source	Reference
Aspergillus sclerotiorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
N-acyl-amine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	2.72	ALOGPS
logP	1.61	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.4 m³·mol⁻¹	ChemAxon
Polarizability	50.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75221150

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid (NP0181557)

MOL for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

3D MOL for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

3D SDF for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

3D-SDF for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

PDB for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

3D PDB for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

SMILES for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

INCHI for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

Structure for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)

3D Structure for NP0181557 (n-(2-hydroxy-6-isopropyl-3,4,7-trimethyl-5,8-dioxo-1,4,7-triazacyclotridec-1-en-9-yl)octa-2,4,6-trienimidic acid)