NP-MRD: Showing NP-Card for Ceplignan (NP0138508)

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Record Information

Version

2.0

Created at

2022-06-29 17:32:46 UTC

Updated at

2022-06-29 17:32:46 UTC

NP-MRD ID

NP0138508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ceplignan

Description

Ceplignan belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Ceplignan was first documented in 2010 (PMID: 21061218). Based on a literature review a small amount of articles have been published on Ceplignan (PMID: 31090297) (PMID: 26296476).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    5.2392   -0.4355    1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4002   -0.5217    0.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2827   -0.4154   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073   -0.2260    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -0.1199   -0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.0787   -0.1315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1859    1.0887   -0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4939    0.8832   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    1.7231   -0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    3.0639   -0.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746    4.0009   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7892    1.2936    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498   -0.0245    0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2094   -0.5371    1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3044   -1.7445    1.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2955    0.3073    1.4141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -0.8585    0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6492   -0.4349    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -1.0874   -0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0305   -2.1934    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674   -3.2027    0.7165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013   -0.2103   -2.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662   -0.3995   -2.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.5022   -1.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7412   -0.6916   -2.2867 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2355   -0.4832    2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7700    0.5358    2.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5928   -1.2616    2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -0.1658    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    0.3916    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1552    3.9904   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9983    3.8982    0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777    5.0140   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6264    1.9603    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6245    0.5993    2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0090   -1.9014    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867   -1.5342   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -2.6361    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   -1.7836    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -4.1008    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838   -0.1374   -2.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4970   -0.4668   -3.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -0.7533   -3.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9 12  2  0
 12 13  1  0
 13 17  2  0
 17 18  1  0
 18  8  2  0
  8  7  1  0
  7  6  1  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 24  2  0
 24 25  1  0
 24 23  1  0
 23 22  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  8  9  1  0
 22  5  1  0
 19 18  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 17 36  1  0
  6 30  1  1
 19 37  1  6
 20 38  1  0
 20 39  1  0
 21 40  1  0
  4 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 43  1  0
 23 42  1  0
 22 41  1  0
 16 35  1  0
M  END


  Mrv1652306292219322D          

 25 27  0  0  1  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    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
  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 10 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC2=C1O[C@@H]([C@H]2CO)C1=CC(OC)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O7/c1-23-14-6-9(3-4-13(14)20)16-12(8-19)11-5-10(18(21)22)7-15(24-2)17(11)25-16/h3-7,12,16,19-20H,8H2,1-2H3,(H,21,22)/t12-,16+/m0/s1

> <INCHI_KEY>
MRHRLMTUTXWEQP-BLLLJJGKSA-N

> <FORMULA>
C18H18O7

> <MOLECULAR_WEIGHT>
346.335

> <EXACT_MASS>
346.10525292

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.10581716812427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.6482292356666663

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.909972967823629

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.104033657388436

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7295485153258428

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
88.5786

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.203   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.743   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.203  -1.897   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.743  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.122  -0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   16   22                                                       
CONECT   22   21                                                            
CONECT   23    5   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₇

Average Mass

346.3350 Da

Monoisotopic Mass

346.10525 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

185244-78-4

SMILES

COC1=CC(=CC2=C1O[C@@H]([C@H]2CO)C1=CC(OC)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C18H18O7/c1-23-14-6-9(3-4-13(14)20)16-12(8-19)11-5-10(18(21)22)7-15(24-2)17(11)25-16/h3-7,12,16,19-20H,8H2,1-2H3,(H,21,22)/t12-,16+/m0/s1

InChI Key

MRHRLMTUTXWEQP-BLLLJJGKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
M-methoxybenzoic acid or derivatives
Methoxyphenol
Coumaran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Primary alcohol
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

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

57256991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004693

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liang RL, Shi GR, Yu SS: [Lignans from seed of Hydnocarpus anthelminthica]. Zhongguo Zhong Yao Za Zhi. 2019 Apr;44(7):1397-1402. doi: 10.19540/j.cnki.cjcmm.20190118.008. [PubMed:31090297 ]
Liang S, Ying SS, Wu HH, Liu YT, Dong PZ, Zhu Y, Xu YT: A novel sesquiterpene and three new phenolic compounds from the rhizomes of Acorus tatarinowii Schott. Bioorg Med Chem Lett. 2015 Oct 1;25(19):4214-8. doi: 10.1016/j.bmcl.2015.08.001. Epub 2015 Aug 6. [PubMed:26296476 ]
Jia L, Bi YF, Jing LL, Zhou SA, Kong DY: Two new compounds from Urena lobata L. J Asian Nat Prod Res. 2010 Nov;12(11):962-7. doi: 10.1080/10286020.2010.510468. [PubMed:21061218 ]

Showing NP-Card for Ceplignan (NP0138508)

MOL for NP0138508 (Ceplignan)

3D MOL for NP0138508 (Ceplignan)

3D SDF for NP0138508 (Ceplignan)

3D-SDF for NP0138508 (Ceplignan)

PDB for NP0138508 (Ceplignan)

3D PDB for NP0138508 (Ceplignan)

SMILES for NP0138508 (Ceplignan)

INCHI for NP0138508 (Ceplignan)

Structure for NP0138508 (Ceplignan)

3D Structure for NP0138508 (Ceplignan)