NP-MRD: Showing NP-Card for Cladrastin (NP0056514)

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Record Information

Version

2.0

Created at

2022-04-28 02:16:29 UTC

Updated at

2022-04-28 02:16:29 UTC

NP-MRD ID

NP0056514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cladrastin

Description

Cladrastin belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, cladrastin is considered to be a flavonoid lipid molecule. Cladrastin is found in Bowdichia virgilioides, Cladrastis kentukea, Cladrastis platycarpa, Cladrastis sikokiana and Millettia pachyloba. Cladrastin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -5.1593   -3.0627   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5007   -1.7323    0.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5797   -0.7115    0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.9570    0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3038    0.0621    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9408   -0.1499    0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.3056    0.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.8995    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.7353    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    1.3331    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6095    1.2001    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473    0.4464    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5148    0.3061    0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4317    0.8751    0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274   -0.1607   -0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -0.9054   -1.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681   -1.5614   -2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -0.0082   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835    2.1600    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    2.3303    0.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.3547    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    1.5617    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0222    0.5692    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3877    0.7795    0.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018   -3.2477   -1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843   -3.7484    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2599   -3.3411    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566   -1.9565    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7504    1.9221    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152    1.6940    1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3407    1.9845    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565    0.6912    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3320    0.4248    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -2.1746   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4680   -2.2817   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463   -0.8062   -3.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3178   -0.4854   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137    3.0159    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469    2.5593    0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7898    1.6917    0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9 18  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
  9  8  1  0
  8 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
 15 12  1  0
  6  8  1  0
  5 21  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 11 30  1  0
 10 29  1  0
 18 37  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 19 38  1  0
 22 39  1  0
 24 40  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
M  END


  Mrv1533004251515142D          

 24 26  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
   -0.7145   -3.7125    0.0000 O   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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  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  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0056514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C1=COC2=CC(O)=C(OC)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-21-14-5-4-10(6-17(14)23-3)12-9-24-15-8-13(19)16(22-2)7-11(15)18(12)20/h4-9,19H,1-3H3

> <INCHI_KEY>
GLSQLYMTPJESIY-UHFFFAOYSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.860033101535336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dimethoxyphenyl)-7-hydroxy-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
2.560989236

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9228975248456655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.366919294050007

> <JCHEM_POLAR_SURFACE_AREA>
74.22

> <JCHEM_REFRACTIVITY>
87.1107

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cladrastin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   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      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   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      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   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                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   14   23                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

3-(3,4-dimethoxyphenyl)-7-hydroxy-6-methoxy-4H-chromen-4-one

Traditional Name

cladrastin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C1=COC2=CC(O)=C(OC)C=C2C1=O

InChI Identifier

InChI=1S/C18H16O6/c1-21-14-5-4-10(6-17(14)23-3)12-9-24-15-8-13(19)16(22-2)7-11(15)18(12)20/h4-9,19H,1-3H3

InChI Key

GLSQLYMTPJESIY-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
Bowdichia virgilioides	LOTUS Database	35616633
Cladrastis kentukea	Plant	KNApSAcK
Cladrastis platycarpa	Plant	KNApSAcK
Cladrastis sikokiana	Plant	KNApSAcK
Millettia pachyloba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylisoflavones

Alternative Parents

Substituents

3p-methoxyisoflavone
4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenol ether
Methoxybenzene
Phenoxy compound
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050116 )

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	3.22	ALOGPS
logP	2.56	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.11 m³·mol⁻¹	ChemAxon
Polarizability	33.86 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

12303305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cladrastin (NP0056514)

MOL for NP0056514 (Cladrastin)

3D MOL for NP0056514 (Cladrastin)

3D SDF for NP0056514 (Cladrastin)

3D-SDF for NP0056514 (Cladrastin)

PDB for NP0056514 (Cladrastin)

3D PDB for NP0056514 (Cladrastin)

SMILES for NP0056514 (Cladrastin)

INCHI for NP0056514 (Cladrastin)

Structure for NP0056514 (Cladrastin)

3D Structure for NP0056514 (Cladrastin)