NP-MRD: Showing NP-Card for Radulanin E (NP0061369)

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Record Information

Version

2.0

Created at

2022-04-28 06:11:06 UTC

Updated at

2022-04-28 06:11:06 UTC

NP-MRD ID

NP0061369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Radulanin E

Description

6-Hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylic acid belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Radulanin E is found in Radula javanica. 6-Hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    6.0550    1.4128    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609    0.5303    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6562    0.2798   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -0.5208   -1.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684   -0.3107   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -0.2996   -2.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813   -0.4777   -3.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0072   -0.1110   -1.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4312    0.0733   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8624    0.2679   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901   -0.9276    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0098   -0.5094    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046   -0.0205    1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7021    0.3750    1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6566    0.2894    0.9191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2861   -0.1998   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9673   -0.5937   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    0.0592    0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361    0.2438    1.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2310    1.4209    2.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0468   -0.7748    2.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8844   -0.1312    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7305   -0.1187    1.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003    0.0733    1.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8615    2.1007    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3111    2.0273   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9538    0.7624    0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673    0.7351   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6037   -0.3433   -2.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8838   -1.6019   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252   -0.4771   -4.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.0993   -2.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    0.6352   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    1.0955    0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697   -1.3356    1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -1.7570   -0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6832    0.0712    2.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9752    0.7513    2.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6834    0.6037    1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0246   -0.2716   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7233   -0.9682   -1.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244   -1.7490    2.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119    0.7175    2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293   -0.9272    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
 22  5  1  0
 17 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 21 42  1  0
 24 43  1  0
 24 44  1  0
M  END


  Mrv1533004231518472D          

 24 26  0  0  0  0            999 V2000
    4.5529    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    0.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3662    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    3.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3662    4.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    3.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    3.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    4.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    4.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    2.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.6874    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2=C(O)C=C(CCC3=CC=CC=C3)C(C(O)=O)=C2OC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-13-7-10-16-17(21)11-15(9-8-14-5-3-2-4-6-14)18(20(22)23)19(16)24-12-13/h2-7,11,21H,8-10,12H2,1H3,(H,22,23)

> <INCHI_KEY>
NVKJHPTXEFDWHJ-UHFFFAOYSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.376

> <EXACT_MASS>
324.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.58974686287394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylic acid

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
4.672327740000001

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.61645906216332

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.830138979357465

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950399839601425

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
93.85269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylic acid

> <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       8.499   3.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.959   3.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.291   2.242   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.789   1.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.585   2.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.251   2.089   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.251   0.549   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.918   2.859   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.918   4.399   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.416   5.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.750   4.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.083   5.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.417   4.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.751   5.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.751   6.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.417   7.479   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.083   6.709   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.251   5.169   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.251   6.709   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.585   7.479   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.918   7.479   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.585   4.399   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.789   5.359   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.291   5.017   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    9   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylate	Generator

Chemical Formula

C₂₀H₂₀O₄

Average Mass

324.3760 Da

Monoisotopic Mass

324.13616 Da

IUPAC Name

6-hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylic acid

Traditional Name

6-hydroxy-3-methyl-8-(2-phenylethyl)-2,5-dihydro-1-benzoxepine-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CCC2=C(O)C=C(CCC3=CC=CC=C3)C(C(O)=O)=C2OC1

InChI Identifier

InChI=1S/C20H20O4/c1-13-7-10-16-17(21)11-15(9-8-14-5-3-2-4-6-14)18(20(22)23)19(16)24-12-13/h2-7,11,21H,8-10,12H2,1H3,(H,22,23)

InChI Key

NVKJHPTXEFDWHJ-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
Radula javanica	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Benzoxepine
Hydroxybenzoic acid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
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	3.78	ALOGPS
logP	4.67	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.85 m³·mol⁻¹	ChemAxon
Polarizability	35.59 Å³	ChemAxon
Number of Rings	3	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

11674225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Radulanin E (NP0061369)

MOL for NP0061369 (Radulanin E)

3D MOL for NP0061369 (Radulanin E)

3D SDF for NP0061369 (Radulanin E)

3D-SDF for NP0061369 (Radulanin E)

PDB for NP0061369 (Radulanin E)

3D PDB for NP0061369 (Radulanin E)

SMILES for NP0061369 (Radulanin E)

INCHI for NP0061369 (Radulanin E)

Structure for NP0061369 (Radulanin E)

3D Structure for NP0061369 (Radulanin E)