NP-MRD: Showing NP-Card for ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate (NP0222593)

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Record Information

Version

2.0

Created at

2022-09-06 00:28:02 UTC

Updated at

2022-09-06 00:28:02 UTC

NP-MRD ID

NP0222593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate

Description

Erinacerin R belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole. ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate is found in Hericium erinaceus. Based on a literature review very few articles have been published on Erinacerin R.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309062202282D          

 23 24  0  0  0  0            999 V2000
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -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
    7.1447   -4.1250    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
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1741   -7.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9946   -7.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3302   -6.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1371   -6.5680    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  1  0  0  0  0
  4  5  2  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
  8 10  2  0  0  0  0
 10 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC\C(C)=C\CC1=C(O)C=C2C(O)=NCC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO5/c1-3-23-15(20)7-5-10(2)4-6-11-14(19)8-12-13(16(11)21)9-18-17(12)22/h4,8,19,21H,3,5-7,9H2,1-2H3,(H,18,22)/b10-4+

> <INCHI_KEY>
DJPYXBQXHRJAHM-ONNFQVAWSA-N

> <FORMULA>
C17H21NO5

> <MOLECULAR_WEIGHT>
319.357

> <EXACT_MASS>
319.14197278

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.29410807302362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.811427536

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.043261735384508

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.364928150733242

> <JCHEM_PKA_STRONGEST_BASIC>
3.4431210066225453

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
87.6991

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (4E)-4-methyl-6-(1,4,6-trihydroxy-3H-isoindol-5-yl)hex-4-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.672  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.992 -13.826   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      20.523 -13.987   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      21.150 -12.580   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.656 -12.260   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   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

C₁₇H₂₁NO₅

Average Mass

319.3570 Da

Monoisotopic Mass

319.14197 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCOC(=O)CC\C(C)=C\CC1=C(O)C=C2C(O)=NCC2=C1O

InChI Identifier

InChI=1S/C17H21NO5/c1-3-23-15(20)7-5-10(2)4-6-11-14(19)8-12-13(16(11)21)9-18-17(12)22/h4,8,19,21H,3,5-7,9H2,1-2H3,(H,18,22)/b10-4+

InChI Key

DJPYXBQXHRJAHM-ONNFQVAWSA-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 isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Cyclic carboximidic acid
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	2.81	ChemAxon
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	3.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.7 m³·mol⁻¹	ChemAxon
Polarizability	34.29 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

78434881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132599516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate (NP0222593)

MOL for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

3D MOL for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

3D SDF for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

3D-SDF for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

PDB for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

3D PDB for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

SMILES for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

INCHI for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

Structure for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)

3D Structure for NP0222593 (ethyl (4e)-4-methyl-6-(1,4,6-trihydroxy-3h-isoindol-5-yl)hex-4-enoate)