NP-MRD: Showing NP-Card for methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate (NP0303931)

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Record Information

Version

2.0

Created at

2022-09-10 18:40:55 UTC

Updated at

2022-09-10 18:40:56 UTC

NP-MRD ID

NP0303931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate

Description

Erinacerin T belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate is found in Hericium erinaceus. Based on a literature review very few articles have been published on Erinacerin T.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.4956   -1.7760    1.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428   -0.9287    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848   -0.8816   -0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7213   -1.6149   -1.4061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0014   -0.0209   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4346    0.7365    0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371    1.6376   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    2.7298   -1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1489    1.5567    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987    0.6144    1.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476    0.0209    0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326   -1.0259   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4363   -1.5842   -0.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -1.5908   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -1.0449   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385    0.0052    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    0.5601    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0075    1.6042    1.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4499    0.3411    0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8652    1.2667    1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -0.5593   -0.0370 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3982   -1.3616   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7331   -2.3973   -1.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3578   -1.2005    1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812   -2.4406    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1013   -2.3688    2.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1911   -0.6163   -1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    0.6998   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2162   -0.0380    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    1.3583    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063    2.9807   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    3.5751   -1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2992    2.2882   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    2.3176   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -0.1808    1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574    1.1442    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189   -1.2477   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -2.4104   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2287    2.0570    2.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8552   -2.2050   -2.5623 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 22  1  0
 22 23  1  0
 22 21  2  0
 21 19  1  0
 19 20  2  0
 19 16  1  0
 16 17  2  0
 17 18  1  0
 17 11  1  0
 16 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 23 40  1  0
 18 39  1  0
M  END

  Mrv1652309102220402D          

 23 24  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0307   -6.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4787   -6.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8512   -6.2557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1867   -5.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9937   -5.3305    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  4  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC(C)=CCC1=C(O)C=C2C(O)=NC(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO6/c1-8(4-6-12(19)23-2)3-5-9-11(18)7-10-13(14(9)20)16(22)17-15(10)21/h3,7,18,20H,4-6H2,1-2H3,(H,17,21,22)

> <INCHI_KEY>
MOBXTHUEHJFZOU-UHFFFAOYSA-N

> <FORMULA>
C16H17NO6

> <MOLECULAR_WEIGHT>
319.313

> <EXACT_MASS>
319.105587271

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.34327426128152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-methyl-6-(3,5,7-trihydroxy-1-oxo-1H-isoindol-6-yl)hex-4-enoate

> <JCHEM_LOGP>
2.547149819666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.079593778053718

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.85780312006013

> <JCHEM_PKA_STRONGEST_BASIC>
-3.131568827547379

> <JCHEM_POLAR_SURFACE_AREA>
116.42

> <JCHEM_REFRACTIVITY>
83.47759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.991 -11.516   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.960 -12.661   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      16.522 -11.677   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      17.149 -10.270   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      18.655  -9.950   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₆

Average Mass

319.3130 Da

Monoisotopic Mass

319.10559 Da

IUPAC Name

methyl 4-methyl-6-(3,5,7-trihydroxy-1-oxo-1H-isoindol-6-yl)hex-4-enoate

Traditional Name

methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC(C)=CCC1=C(O)C=C2C(O)=NC(=O)C2=C1O

InChI Identifier

InChI=1S/C16H17NO6/c1-8(4-6-12(19)23-2)3-5-9-11(18)7-10-13(14(9)20)16(22)17-15(10)21/h3,7,18,20H,4-6H2,1-2H3,(H,17,21,22)

InChI Key

MOBXTHUEHJFZOU-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
Hericium erinaceus	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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid methyl ester
Fatty acid ester
Fatty acyl
Benzenoid
Vinylogous acid
Methyl ester
Carboxylic acid ester
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.55	ChemAxon
pKa (Strongest Acidic)	5.86	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.48 m³·mol⁻¹	ChemAxon
Polarizability	32.34 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

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

139584511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate (NP0303931)

MOL for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

3D MOL for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

3D SDF for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

3D-SDF for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

PDB for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

3D PDB for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

SMILES for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

INCHI for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

Structure for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)

3D Structure for NP0303931 (methyl 4-methyl-6-(1,4,6-trihydroxy-3-oxoisoindol-5-yl)hex-4-enoate)