NP-MRD: Showing NP-Card for n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid (NP0219618)

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Record Information

Version

1.0

Created at

2022-09-05 20:40:36 UTC

Updated at

2022-09-05 20:40:37 UTC

NP-MRD ID

NP0219618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid

Description

N-methyl-4-(N-methylformamido)-1-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)-1H-imidazole-5-carboximidic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid is found in Leptogorgia gilchristi. N-methyl-4-(N-methylformamido)-1-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)-1H-imidazole-5-carboximidic acid is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513452D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161513452D          

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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  4  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(=O)C1=C(N=CN1CC=C(C)CCC=C(C)CCCC(C)=CC(=O)CC(C)C)N(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42N4O3/c1-20(2)16-24(33)17-23(5)13-9-11-21(3)10-8-12-22(4)14-15-31-18-29-26(30(7)19-32)25(31)27(34)28-6/h10,14,17-20H,8-9,11-13,15-16H2,1-7H3,(H,28,34)

> <INCHI_KEY>
BRGBNADJYSOXIE-UHFFFAOYSA-N

> <FORMULA>
C27H42N4O3

> <MOLECULAR_WEIGHT>
470.658

> <EXACT_MASS>
470.325691228

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54326452916321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methyl-4-(N-methylformamido)-1-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)-1H-imidazole-5-carboxamide

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
4.646800417333332

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.085772330148846

> <JCHEM_PKA_STRONGEST_BASIC>
1.5886162915146433

> <JCHEM_POLAR_SURFACE_AREA>
84.30000000000001

> <JCHEM_REFRACTIVITY>
141.85809999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-5-(N-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.274   4.390   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.260   1.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.580   2.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.404   0.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.869   0.542   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.013  -0.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.478  -0.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.798   1.493   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.622  -1.043   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.087  -0.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.231  -1.598   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.696  -1.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -15.016   0.384   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -16.481   0.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -17.625  -0.170   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -16.801   2.366   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -18.266   2.842   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -18.586   4.349   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -19.410   1.812   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -15.840  -2.153   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       3.770   1.651   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       4.091   3.157   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.915   0.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.379   1.096   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   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   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   22                                                            
CONECT   31    6   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
N-Methyl-4-(N-methylformamido)-1-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)-1H-imidazole-5-carboximidate	Generator

Chemical Formula

C₂₇H₄₂N₄O₃

Average Mass

470.6580 Da

Monoisotopic Mass

470.32569 Da

IUPAC Name

N-methyl-4-(N-methylformamido)-1-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)-1H-imidazole-5-carboxamide

Traditional Name

N-methyl-5-(N-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboxamide

CAS Registry Number

Not Available

SMILES

CNC(=O)C1=C(N=CN1CC=C(C)CCC=C(C)CCCC(C)=CC(=O)CC(C)C)N(C)C=O

InChI Identifier

InChI=1S/C27H42N4O3/c1-20(2)16-24(33)17-23(5)13-9-11-21(3)10-8-12-22(4)14-15-31-18-29-26(30(7)19-32)25(31)27(34)28-6/h10,14,17-20H,8-9,11-13,15-16H2,1-7H3,(H,28,34)

InChI Key

BRGBNADJYSOXIE-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
Leptogorgia gilchristi	LOTUS Database	35616633

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
N-substituted imidazole
Imidolactam
Acryloyl-group
Azole
Enone
Heteroaromatic compound
Imidazole
Alpha,beta-unsaturated ketone
Tertiary carboxylic acid amide
Carboxamide group
Ketone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
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
logP	4.4	ALOGPS
logP	4.65	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	141.86 m³·mol⁻¹	ChemAxon
Polarizability	54.54 Å³	ChemAxon
Number of Rings	1	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

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

73005097

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid (NP0219618)

MOL for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

3D MOL for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

3D SDF for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

3D-SDF for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

PDB for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

3D PDB for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

SMILES for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

INCHI for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

Structure for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)

3D Structure for NP0219618 (n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid)