NP-MRD: Showing NP-Card for (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (NP0037835)

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Record Information

Version

2.0

Created at

2021-06-20 20:40:04 UTC

Updated at

2021-06-30 00:10:17 UTC

NP-MRD ID

NP0037835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-3-ethyl-7-hydroxy-6-methoxyphthalide

Provided By

JEOL Database JEOL Logo

Description

CHEMBL502750 belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. (S)-3-ethyl-7-hydroxy-6-methoxyphthalide is found in Pittosporum illicioides and Pittosporum illicioides var. illicioides. (S)-3-ethyl-7-hydroxy-6-methoxyphthalide was first documented in 2008 (Chou, T.-H., et al.). Based on a literature review very few articles have been published on CHEMBL502750.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122403D          

 27 28  0  0  0  0            999 V2000
   -2.5543    2.9195   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798    1.7491   -1.3905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5035    0.4100   -1.7834 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8783    0.3643   -1.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1258   -0.6750   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2009   -0.9182    0.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613   -1.3901   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8980   -0.7518   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956   -1.2278   -1.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713   -2.3657   -0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480   -3.0123    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486   -4.1295    1.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665   -4.6731    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593   -2.5133    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -3.1426    1.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840    2.8160   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0698    3.8593   -1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6120    2.9913   -1.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    1.7554   -1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668    1.9041   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    0.2622   -2.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643   -0.7342   -1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -2.7252   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -3.9558    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2576   -5.5484    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668   -5.0084    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591   -3.8965    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 14  1  0  0  0  0
  8  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
 14 11  2  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 10  9  2  0  0  0  0
 14 15  1  0  0  0  0
  9  8  1  0  0  0  0
 11 12  1  0  0  0  0
 11 10  1  0  0  0  0
 12 13  1  0  0  0  0
 10 23  1  0  0  0  0
  9 22  1  0  0  0  0
  3 21  1  6  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
 15 27  1  0  0  0  0
 13 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
M  END


  Mrv1652306202122403D          

 27 28  0  0  0  0            999 V2000
   -2.5543    2.9195   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798    1.7491   -1.3905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5035    0.4100   -1.7834 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8783    0.3643   -1.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1258   -0.6750   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2009   -0.9182    0.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613   -1.3901   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8980   -0.7518   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956   -1.2278   -1.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713   -2.3657   -0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480   -3.0123    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486   -4.1295    1.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665   -4.6731    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593   -2.5133    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -3.1426    1.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840    2.8160   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0698    3.8593   -1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6120    2.9913   -1.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    1.7554   -1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668    1.9041   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    0.2622   -2.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643   -0.7342   -1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -2.7252   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -3.9558    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2576   -5.5484    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668   -5.0084    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591   -3.8965    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 14  1  0  0  0  0
  8  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
 14 11  2  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 10  9  2  0  0  0  0
 14 15  1  0  0  0  0
  9  8  1  0  0  0  0
 11 12  1  0  0  0  0
 11 10  1  0  0  0  0
 12 13  1  0  0  0  0
 10 23  1  0  0  0  0
  9 22  1  0  0  0  0
  3 21  1  6  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
 15 27  1  0  0  0  0
 13 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C2=C1C(=O)O[C@@]2([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c1-3-7-6-4-5-8(14-2)10(12)9(6)11(13)15-7/h4-5,7,12H,3H2,1-2H3/t7-/m0/s1

> <INCHI_KEY>
CJPMLOYFDLJAKU-ZETCQYMHSA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.213

> <EXACT_MASS>
208.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.27867145563661

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-ethyl-7-hydroxy-6-methoxy-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.6558109136666666

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.84800528435732

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.116041574421136

> <JCHEM_PKA_STRONGEST_BASIC>
-3.440559592664294

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
54.02480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-ethyl-7-hydroxy-6-methoxy-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.554   2.920  -2.093  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.880   1.749  -1.391  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.503   0.410  -1.783  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.878   0.364  -1.346  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.126  -0.675  -0.487  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.201  -0.918   0.020  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.861  -1.390  -0.332  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.898  -0.752  -1.090  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.596  -1.228  -1.130  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.271  -2.366  -0.380  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.248  -3.012   0.395  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.049  -4.130   1.167  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.267  -4.673   1.183  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.559  -2.513   0.414  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.509  -3.143   1.165  0.00  0.00           O+0
HETATM   16  H   UNK     0      -2.484   2.816  -3.181  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.070   3.859  -1.810  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.612   2.991  -1.821  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.811   1.755  -1.635  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.967   1.904  -0.308  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.490   0.262  -2.869  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.164  -0.734  -1.730  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.752  -2.725  -0.420  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.985  -3.956   1.594  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.258  -5.548   1.840  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.567  -5.008   0.185  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.059  -3.897   1.592  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    3    1   19   20                                             
CONECT    3    8    4    2   21                                             
CONECT    4    3    5                                                       
CONECT    5    4    7    6                                                  
CONECT    6    5                                                            
CONECT    7   14    5    8                                                  
CONECT    8    3    7    9                                                  
CONECT    9   10    8   22                                                  
CONECT   10    9   11   23                                                  
CONECT   11   14   12   10                                                  
CONECT   12   11   13                                                       
CONECT   13   12   24   25   26                                             
CONECT   14    7   11   15                                                  
CONECT   15   14   27                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    2                                                            
CONECT   21    3                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   13                                                            
CONECT   25   13                                                            
CONECT   26   13                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₄

Average Mass

208.2130 Da

Monoisotopic Mass

208.07356 Da

IUPAC Name

(3S)-3-ethyl-7-hydroxy-6-methoxy-1,3-dihydro-2-benzofuran-1-one

Traditional Name

(3S)-3-ethyl-7-hydroxy-6-methoxy-3H-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C2=C1C(=O)O[C@@]2([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C11H12O4/c1-3-7-6-4-5-8(14-2)10(12)9(6)11(13)15-7/h4-5,7,12H,3H2,1-2H3/t7-/m0/s1

InChI Key

CJPMLOYFDLJAKU-ZETCQYMHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pittosporum illicioides	LOTUS Database	35616633
Pittosporum illicioides var. illicioides	JEOL database	Chou, T.-H., et al, J. Nat. Prod. 71, 1692 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

Alternative Parents

Substituents

Isobenzofuranone
Benzofuranone
Phthalide
Isocoumaran
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Ether
Carboxylic acid derivative
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	2.56	ALOGPS
logP	2.66	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.02 m³·mol⁻¹	ChemAxon
Polarizability	21.28 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

24710054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25137302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chou, T.-H., et al. (2008). Chou, T.-H., et al, J. Nat. Prod. 71, 1692 (2008). J. Nat. Prod..

Showing NP-Card for (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (NP0037835)

MOL for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

3D MOL for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

3D SDF for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

3D-SDF for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

PDB for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

3D PDB for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

SMILES for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

INCHI for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

Structure for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)

3D Structure for NP0037835 ((S)-3-ethyl-7-hydroxy-6-methoxyphthalide)