NP-MRD: Showing NP-Card for Evofolin B (NP0138651)

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Record Information

Version

1.0

Created at

2022-06-29 17:39:22 UTC

Updated at

2022-06-29 17:39:22 UTC

NP-MRD ID

NP0138651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Evofolin B

Description

Evofolin B 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. Evofolin B is found in Anastatica hierochuntica, Carya cathayensis, Couepia ulei, Daphne feddei, Tetradium glabrifolium, Isatis tinctoria, Microtropis japonica, Sida acuta and Zanthoxylum ailanthoides. Evofolin B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    1.5977   -1.2677   -2.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166   -0.5524   -2.3743 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517    0.4255   -1.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5830    0.7489   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5244    1.7205    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787    2.0273    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    2.9558    1.7751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0234    1.4161    0.6654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1254    2.1213    1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636    3.5048    1.2610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1575   -0.0023    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829   -0.5862    2.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -1.9407    2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928   -2.7443    1.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6635   -4.1154    1.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -2.1518    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5864   -2.9161   -0.7942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0519   -2.3000   -1.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -0.7924    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    2.3697    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8783    2.0411   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    1.0746   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314    0.7824   -1.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -2.1353   -2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -1.6898   -3.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -0.6582   -2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    0.2172   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    1.5999   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1196    1.7787    1.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    1.9538    2.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9217    3.8925    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2039    0.0579    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155   -2.3958    3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131   -4.6633    0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322   -1.7217   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4590   -3.0688   -2.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8468   -1.5607   -1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1657   -0.3829   -0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    3.1243    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7890    2.5477    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9666    1.2858   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 19  2  0
 19 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
 14 16  1  0
  4  5  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
M  END


  Mrv1533004201503392D          

 23 24  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    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
    3.5724   -2.8875    0.0000 O   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
    5.7158   -4.1250    0.0000 C   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 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
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(CO)C(=O)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O6/c1-22-15-7-10(3-5-13(15)19)12(9-18)17(21)11-4-6-14(20)16(8-11)23-2/h3-8,12,18-20H,9H2,1-2H3

> <INCHI_KEY>
QMYGRGKKZBRZKH-UHFFFAOYSA-N

> <FORMULA>
C17H18O6

> <MOLECULAR_WEIGHT>
318.325

> <EXACT_MASS>
318.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.50108642586246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)propan-1-one

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.7049751013333339

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.94100793695766

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.225058755933173

> <JCHEM_PKA_STRONGEST_BASIC>
-2.70098538708101

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
84.4201

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
evofolin B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₆

Average Mass

318.3250 Da

Monoisotopic Mass

318.11034 Da

IUPAC Name

3-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)propan-1-one

Traditional Name

evofolin B

CAS Registry Number

168254-96-4

SMILES

COC1=CC(=CC=C1O)C(CO)C(=O)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C17H18O6/c1-22-15-7-10(3-5-13(15)19)12(9-18)17(21)11-4-6-14(20)16(8-11)23-2/h3-8,12,18-20H,9H2,1-2H3

InChI Key

QMYGRGKKZBRZKH-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
Anastatica hierochuntica	LOTUS Database	35616633
Carya cathayensis	LOTUS Database	35616633
Couepia ulei	LOTUS Database	35616633
Daphne feddei	LOTUS Database	35616633
Euodia fargesii	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Microtropis japonica	LOTUS Database	35616633
Sida acuta	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633

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
Alkyl-phenylketone
Methoxyphenol
Phenylketone
Phenoxy compound
Phenol ether
Benzoyl
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Beta-hydroxy ketone
Monocyclic benzene moiety
Ketone
Ether
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.12	ALOGPS
logP	1.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.42 m³·mol⁻¹	ChemAxon
Polarizability	32.5 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

5317306

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Evofolin B (NP0138651)

MOL for NP0138651 (Evofolin B)

3D MOL for NP0138651 (Evofolin B)

3D SDF for NP0138651 (Evofolin B)

3D-SDF for NP0138651 (Evofolin B)

PDB for NP0138651 (Evofolin B)

3D PDB for NP0138651 (Evofolin B)

SMILES for NP0138651 (Evofolin B)

INCHI for NP0138651 (Evofolin B)

Structure for NP0138651 (Evofolin B)

3D Structure for NP0138651 (Evofolin B)