NP-MRD: Showing NP-Card for Zinnimidine (NP0051386)

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Record Information

Version

2.0

Created at

2022-04-27 22:46:24 UTC

Updated at

2022-04-27 22:46:24 UTC

NP-MRD ID

NP0051386

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Zinnimidine

Description

7-Methoxy-6-methyl-5-[(3-methylbut-2-en-1-yl)oxy]-1H-isoindol-3-ol belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Zinnimidine is found in Alternaria cichorii, Alternaria porri and Pestalotiopsis photiniae. 7-Methoxy-6-methyl-5-[(3-methylbut-2-en-1-yl)oxy]-1H-isoindol-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.3016   -1.4796   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186   -0.9000    0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496   -0.1495    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -0.7031    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702   -2.1804    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622    0.0568    0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9342   -0.5863    0.8408 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.1248    0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.7916    1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943   -0.9329    0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.1733   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4101   -1.8670    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3513    1.4171    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836    2.0317    0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7002    1.2315    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8652    2.0677   -0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    3.4017   -0.3389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    3.4173   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2157    4.4174   -0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2683   -0.9639   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5266   -2.5507   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -1.2639   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -2.5153    0.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -2.3549    1.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670   -2.7080    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465    0.6232   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955    0.8604    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2437   -1.3698    2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3803   -0.3271   -1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2517    0.9114   -0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -0.6083   -1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638   -2.5717    1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2851   -1.2104    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7009   -2.3531   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517    2.0085    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2251    1.7808   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800    1.9694    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9864    4.2411   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  6 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 15  3  1  0
 18 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv1533004231519462D          

 19 20  0  0  0  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 14 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051386

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(OCC=C(C)C)=CC2=C1CNC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO3/c1-9(2)5-6-19-13-7-11-12(8-16-15(11)17)14(18-4)10(13)3/h5,7H,6,8H2,1-4H3,(H,16,17)

> <INCHI_KEY>
DSOITGJEUKHAJN-UHFFFAOYSA-N

> <FORMULA>
C15H19NO3

> <MOLECULAR_WEIGHT>
261.321

> <EXACT_MASS>
261.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.921058258626182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-5-methyl-6-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydro-1H-isoindol-1-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.358114425

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.152881797282543

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.782829845753653

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3196053076563028

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
75.67349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-5-methyl-6-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydroisoindol-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.455  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       2.417   0.770   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3   14                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉NO₃

Average Mass

261.3210 Da

Monoisotopic Mass

261.13649 Da

IUPAC Name

4-methoxy-5-methyl-6-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydro-1H-isoindol-1-one

Traditional Name

4-methoxy-5-methyl-6-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydroisoindol-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(OCC=C(C)C)=CC2=C1CNC2=O

InChI Identifier

InChI=1S/C15H19NO3/c1-9(2)5-6-19-13-7-11-12(8-16-15(11)17)14(18-4)10(13)3/h5,7H,6,8H2,1-4H3,(H,16,17)

InChI Key

DSOITGJEUKHAJN-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Alternaria cichorii	Fungi	KNApSAcK
Alternaria porri	LOTUS Database	35616633
Pestalotiopsis photiniae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
Anisole
Alkyl aryl ether
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoindoles (CHEBI:10116 )

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	2.11	ALOGPS
logP	2.36	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.67 m³·mol⁻¹	ChemAxon
Polarizability	28.92 Å³	ChemAxon
Number of Rings	2	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

C00002370

Chemspider ID

Not Available

KEGG Compound ID

C10626

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442878

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Zinnimidine (NP0051386)

MOL for NP0051386 (Zinnimidine)

3D MOL for NP0051386 (Zinnimidine)

3D SDF for NP0051386 (Zinnimidine)

3D-SDF for NP0051386 (Zinnimidine)

PDB for NP0051386 (Zinnimidine)

3D PDB for NP0051386 (Zinnimidine)

SMILES for NP0051386 (Zinnimidine)

INCHI for NP0051386 (Zinnimidine)

Structure for NP0051386 (Zinnimidine)

3D Structure for NP0051386 (Zinnimidine)