NP-MRD: Showing NP-Card for echitin (NP0033756)

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Record Information

Version

2.0

Created at

2021-06-20 17:41:05 UTC

Updated at

2021-06-30 00:03:44 UTC

NP-MRD ID

NP0033756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

echitin

Provided By

JEOL Database JEOL Logo

Description

2''-O-(4-Hydroxy-E-cinnamoyl)cosmosiin belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. echitin is found in Echinops echinatus and Itoa orientalis. echitin was first documented in 2008 (Chai, X. Y., et al.). Based on a literature review very few articles have been published on 2''-O-(4-Hydroxy-E-cinnamoyl)cosmosiin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119413D          

 68 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202119413D          

 68 72  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0033756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@@]2([H])[C@]([H])(OC3=C([H])C(O[H])=C4C(=O)C([H])=C(OC4=C3[H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c31-14-24-27(37)28(38)29(42-25(36)10-3-15-1-6-17(32)7-2-15)30(41-24)39-19-11-20(34)26-21(35)13-22(40-23(26)12-19)16-4-8-18(33)9-5-16/h1-13,24,27-34,37-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
XDGSYLNVWAOCRH-ZZSHFKPLSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
59.15011299650329

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
3.168946436666666

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.658426035769228

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.294173807698767

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092991485716

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
146.60690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 11 49  1  0
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M  END

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  O   UNK     0       1.821   1.406  -4.497  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.964   0.801  -3.874  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.425   0.574  -4.311  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.834   1.040  -5.501  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.200   0.882  -6.018  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.952  -0.284  -5.814  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.239  -0.405  -6.346  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.772   0.639  -7.093  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.022   0.565  -7.631  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.038   1.796  -7.320  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.752   1.915  -6.788  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.143   0.201  -2.676  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.426   0.422  -2.028  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.226   0.141  -0.522  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.338   1.153  -0.023  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.721   0.934   1.177  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.331   1.812   1.459  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.044   1.702   2.651  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.065   2.591   2.847  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.702   0.717   3.578  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.423   0.566   4.846  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.366   1.296   5.132  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.966  -0.495   5.754  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.072  -1.262   5.388  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.581  -2.347   6.252  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.704  -2.185   7.641  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.199  -3.220   8.439  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.581  -4.420   7.854  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.060  -5.400   8.671  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.480  -4.604   6.481  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.983  -3.567   5.684  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.744  -1.137   4.180  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.350  -0.152   3.308  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.063  -0.048   2.109  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.471   0.187   0.177  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.378  -0.831  -0.275  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.608  -0.796   0.638  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.194  -0.980   1.994  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.751  -0.575  -1.733  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.618  -1.596  -2.229  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.492  -0.524  -2.609  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.941  -0.156  -3.927  0.00  0.00           O+0
HETATM   43  H   UNK     0      -1.079   0.045  -3.630  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.148   1.595  -6.140  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.542  -1.119  -5.250  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.802  -1.317  -6.173  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.415  -0.291  -7.391  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.463   2.603  -7.909  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.190   2.828  -6.976  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.723   1.470  -2.168  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.752  -0.844  -0.402  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.600   2.587   0.744  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.474   2.402   3.722  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.506  -0.607   6.685  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.432  -1.248   8.122  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.292  -3.086   9.514  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.313  -6.163   8.126  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.781  -5.536   6.013  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.909  -3.724   4.609  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.888  -0.734   1.944  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.896  -1.810  -0.153  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.119   0.171   0.582  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.319  -1.588   0.387  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.549  -0.269   2.168  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.288   0.378  -1.824  0.00  0.00           H+0
HETATM   66  H   UNK     0       5.669  -1.441  -3.195  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.070  -1.530  -2.720  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.319   0.498  -4.314  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   12    3    1                                                  
CONECT    3    2    4   43                                                  
CONECT    4    3    5   44                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7   45                                                  
CONECT    7    6    8   46                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   47                                                       
CONECT   10    8   11   48                                                  
CONECT   11   10    5   49                                                  
CONECT   12    2   13                                                       
CONECT   13   14   41   12   50                                             
CONECT   14   13   35   15   51                                             
CONECT   15   16   14                                                       
CONECT   16   17   15   34                                                  
CONECT   17   16   18   52                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   53                                                       
CONECT   20   21   18   33                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   24   54                                                  
CONECT   24   23   32   25                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   55                                                  
CONECT   27   26   28   56                                                  
CONECT   28   27   30   29                                                  
CONECT   29   28   57                                                       
CONECT   30   28   31   58                                                  
CONECT   31   30   25   59                                                  
CONECT   32   24   33                                                       
CONECT   33   34   20   32                                                  
CONECT   34   33   16   60                                                  
CONECT   35   36   14                                                       
CONECT   36   39   35   37   61                                             
CONECT   37   38   36   62   63                                             
CONECT   38   37   64                                                       
CONECT   39   41   36   40   65                                             
CONECT   40   39   66                                                       
CONECT   41   13   39   42   67                                             
CONECT   42   41   68                                                       
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    6                                                            
CONECT   46    7                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   14                                                            
CONECT   52   17                                                            
CONECT   53   19                                                            
CONECT   54   23                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   29                                                            
CONECT   58   30                                                            
CONECT   59   31                                                            
CONECT   60   34                                                            
CONECT   61   36                                                            
CONECT   62   37                                                            
CONECT   63   37                                                            
CONECT   64   38                                                            
CONECT   65   39                                                            
CONECT   66   40                                                            
CONECT   67   41                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
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  9 47  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@@]2([H])[C@]([H])(OC3=C([H])C(O[H])=C4C(=O)C([H])=C(OC4=C3[H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C30H26O12/c31-14-24-27(37)28(38)29(42-25(36)10-3-15-1-6-17(32)7-2-15)30(41-24)39-19-11-20(34)26-21(35)13-22(40-23(26)12-19)16-4-8-18(33)9-5-16/h1-13,24,27-34,37-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m1/s1

InChI Key

XDGSYLNVWAOCRH-ZZSHFKPLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Echinops echinatus	Plant	KNApSAcK
Itoa orientalis	JEOL database	Chai, X. Y., et al, J. Nat. Prod. 71, 814 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Fatty acid ester
Pyranone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Primary alcohol
Organic oxygen compound
Organic oxide
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	2.87	ALOGPS
logP	3.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	146.61 m³·mol⁻¹	ChemAxon
Polarizability	59.15 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

101422301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chai, X. Y., et al. (2008). Chai, X. Y., et al, J. Nat. Prod. 71, 814 (2008) . J. Nat. Prod..

Showing NP-Card for echitin (NP0033756)

MOL for NP0033756 (echitin)

3D MOL for NP0033756 (echitin)

3D SDF for NP0033756 (echitin)

3D-SDF for NP0033756 (echitin)

PDB for NP0033756 (echitin)

3D PDB for NP0033756 (echitin)

SMILES for NP0033756 (echitin)

INCHI for NP0033756 (echitin)

Structure for NP0033756 (echitin)

3D Structure for NP0033756 (echitin)