NP-MRD: Showing NP-Card for 2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate (NP0208090)

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Record Information

Version

2.0

Created at

2022-09-05 04:57:38 UTC

Updated at

2022-09-05 04:57:38 UTC

NP-MRD ID

NP0208090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate

Description

11-Hydroxy-3-{2-[(1H-indol-3-yl)methyl]-5-methyl-1,4-dioxo-3,4-dihydro-2H-1λ⁵-imidazol-2-yl}-6,14-dimethyl-1,7-dioxacyclotetradec-9-ene-2,5,8-trione belongs to the class of organic compounds known as alpha-imino acid and derivatives. These are organic acids containing an imino group attached to a carbon, which in turn is immediately linked to a carboxyl group (or a derivative thereof). 2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate is found in Clonostachys rogersoniana. Based on a literature review very few articles have been published on 11-hydroxy-3-{2-[(1H-indol-3-yl)methyl]-5-methyl-1,4-dioxo-3,4-dihydro-2H-1λ⁵-imidazol-2-yl}-6,14-dimethyl-1,7-dioxacyclotetradec-9-ene-2,5,8-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206572D          

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M  CHG  2   3   1   4  -1
M  END

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M  CHG  2   3   1   4  -1
M  END


  Mrv1652309052206572D          

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   -2.7206   -1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -1.4549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 10 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  4  0  0  0
 25 26  2  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
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  2  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  CHG  2   3   1   4  -1
M  END
> <DATABASE_ID>
NP0208090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(O)C=CC(=O)OC(C)C(=O)CC(C(=O)O1)C1(CC2=CNC3=CC=CC=C23)NC(=O)C(C)=[N+]1[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C27H31N3O8/c1-15-8-9-19(31)10-11-24(33)38-17(3)23(32)12-21(26(35)37-15)27(29-25(34)16(2)30(27)36)13-18-14-28-22-7-5-4-6-20(18)22/h4-7,10-11,14-15,17,19,21,28,31H,8-9,12-13H2,1-3H3,(H,29,34)

> <INCHI_KEY>
ULJPJPAWVJZGME-UHFFFAOYSA-N

> <FORMULA>
C27H31N3O8

> <MOLECULAR_WEIGHT>
525.558

> <EXACT_MASS>
525.21111497

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.21728765056379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-[(1H-indol-3-yl)methyl]-4-methyl-5-oxo-2,5-dihydro-1H-imidazol-3-ium-3-olate

> <JCHEM_LOGP>
-0.39974044780507895

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.34168845213867

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.218969242280587

> <JCHEM_PKA_STRONGEST_BASIC>
-2.873618078231914

> <JCHEM_POLAR_SURFACE_AREA>
160.85999999999999

> <JCHEM_REFRACTIVITY>
137.57880000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1H-indol-3-ylmethyl)-5-methyl-4-oxo-3H-imidazol-1-ium-1-olate

> <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      -4.935  -5.617   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.308  -4.211   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.802  -3.890   0.000  0.00  0.00           N+1
HETATM    4  O   UNK     0      -2.482  -5.397   0.000  0.00  0.00           O-1
HETATM    5  C   UNK     0      -2.641  -2.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.135  -2.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.659  -4.144   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.564  -5.389   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.659  -6.635   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.806  -6.159   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.139  -6.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.473  -6.159   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.473  -4.619   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.139  -3.849   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.806  -4.619   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.165  -0.894   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.672  -1.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.702  -0.070   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.208  -0.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.226   1.395   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.257   2.539   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.720   1.715   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.244   3.180   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.274   4.324   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.738   3.500   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.293   2.355   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.799   2.675   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.275   4.140   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.830   1.531   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.354   0.066   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.848  -0.254   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.183   0.891   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.372  -1.718   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.135  -2.039   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.230  -3.284   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0      -4.048  -1.732   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      -5.078  -2.877   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.610  -2.716   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16   36                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   10                                                  
CONECT   16    5   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   16   35                                                  
CONECT   35   34                                                            
CONECT   36    5   37                                                       
CONECT   37   36    2   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁N₃O₈

Average Mass

525.5580 Da

Monoisotopic Mass

525.21111 Da

IUPAC Name

2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-[(1H-indol-3-yl)methyl]-4-methyl-5-oxo-2,5-dihydro-1H-imidazol-3-ium-3-olate

Traditional Name

2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1H-indol-3-ylmethyl)-5-methyl-4-oxo-3H-imidazol-1-ium-1-olate

CAS Registry Number

Not Available

SMILES

CC1CCC(O)C=CC(=O)OC(C)C(=O)CC(C(=O)O1)C1(CC2=CNC3=CC=CC=C23)NC(=O)C(C)=[N+]1[O-]

InChI Identifier

InChI=1S/C27H31N3O8/c1-15-8-9-19(31)10-11-24(33)38-17(3)23(32)12-21(26(35)37-15)27(29-25(34)16(2)30(27)36)13-18-14-28-22-7-5-4-6-20(18)22/h4-7,10-11,14-15,17,19,21,28,31H,8-9,12-13H2,1-3H3,(H,29,34)

InChI Key

ULJPJPAWVJZGME-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
Clonostachys rogersoniana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-imino acid and derivatives. These are organic acids containing an imino group attached to a carbon, which in turn is immediately linked to a carboxyl group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Alpha-imino acid and derivatives

Direct Parent

Alpha-imino acid and derivatives

Alternative Parents

Substituents

Alpha-imino acid or derivatives
3-alkylindole
Indole or derivatives
Indole
Alpha-acyloxy ketone
Benzenoid
Substituted pyrrole
Imidazolinone
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrole
3-imidazoline
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Nitrone
Lactone
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.4	ChemAxon
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	160.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	137.58 m³·mol⁻¹	ChemAxon
Polarizability	52.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

163194456

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate (NP0208090)

MOL for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

3D MOL for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

3D SDF for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

3D-SDF for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

PDB for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

3D PDB for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

SMILES for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

INCHI for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

Structure for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)

3D Structure for NP0208090 (2-(11-hydroxy-6,14-dimethyl-2,5,8-trioxo-1,7-dioxacyclotetradec-9-en-3-yl)-2-(1h-indol-3-ylmethyl)-5-methyl-4-oxo-3h-imidazol-1-ium-1-olate)