NP-MRD: Showing NP-Card for Dryopterin (NP0056442)

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Record Information

Version

2.0

Created at

2022-04-28 02:13:31 UTC

Updated at

2022-04-28 02:13:31 UTC

NP-MRD ID

NP0056442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dryopterin

Description

Dryopterin belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. Thus, dryopterin is considered to be a flavonoid. Dryopterin is found in Dryopteris filix-mas . Based on a literature review very few articles have been published on Dryopterin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -3.8026    1.8716   -3.0743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3741    1.1033   -2.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605    0.4405   -2.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2439    0.3723   -1.1539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0440    0.1324    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761    0.3780    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0926    0.1374    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913   -0.3448    2.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1709   -0.5917    3.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501   -0.5959    2.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -0.3618    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1003   -0.5966    1.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -1.1211   -0.0609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9261   -0.8936    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856   -1.9087   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1563   -1.7503   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555   -0.5375    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0543   -0.4319    0.3417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8195    0.5086    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608    1.6967    1.0266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379    0.3003    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964   -0.5764   -1.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9103    0.0438   -2.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0806    0.8638   -0.9985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184    0.9665   -3.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973   -0.6233   -2.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8023    1.4093   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1578    0.3417    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411    0.1578    4.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6528   -0.9823    3.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -2.2249   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377   -2.8865   -0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7846   -2.5781   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    0.4488    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    2.5088    1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    1.1488    0.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369   -1.4197   -1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032    0.8059   -2.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 24  1  0
 24  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 11  5  1  0
 13 22  1  0
 21 14  1  0
  5  4  1  0
  5  6  2  0
 23 38  1  0
 22 37  1  6
  4 27  1  1
  3 25  1  0
  3 26  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  6
 15 32  1  0
 16 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
M  END


  Mrv1652304282204132D          

 24 27  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.7145   -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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    0.0000    3.3000    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
    1.4289    3.3000    0.0000 C   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    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   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  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
  9 15  1  6  0  0  0
  8 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H]2CC(=O)OC3=CC(O)=CC(O[C@@H]1C1=CC=C(O)C(O)=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c18-8-4-12-15-9(6-14(21)23-12)16(22)17(24-13(15)5-8)7-1-2-10(19)11(20)3-7/h1-5,9,16-20,22H,6H2/t9-,16+,17+/m0/s1

> <INCHI_KEY>
CWTCSQCPFXJPDL-SZQIBGDISA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.292

> <EXACT_MASS>
330.073952791

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.507108267554486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R,7R)-7-(3,4-dihydroxyphenyl)-6,11-dihydroxy-2,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13),10-trien-3-one

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.4185787520000002

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.394892907975493

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.752337598894668

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3973762419410303

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
81.2455

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R,7R)-7-(3,4-dihydroxyphenyl)-6,11-dihydroxy-2,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13),10-trien-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4                                                       
CONECT   15    9                                                            
CONECT   16    8   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20                                                            
CONECT   23   19                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2920 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

(5S,6R,7R)-7-(3,4-dihydroxyphenyl)-6,11-dihydroxy-2,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13),10-trien-3-one

Traditional Name

(5S,6R,7R)-7-(3,4-dihydroxyphenyl)-6,11-dihydroxy-2,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13),10-trien-3-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H]2CC(=O)OC3=CC(O)=CC(O[C@@H]1C1=CC=C(O)C(O)=C1)=C23

InChI Identifier

InChI=1S/C17H14O7/c18-8-4-12-15-9(6-14(21)23-12)16(22)17(24-13(15)5-8)7-1-2-10(19)11(20)3-7/h1-5,9,16-20,22H,6H2/t9-,16+,17+/m0/s1

InChI Key

CWTCSQCPFXJPDL-SZQIBGDISA-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
Dryopteris filix-mas	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
3,4-dihydrocoumarin
1-benzopyran
Chromane
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Secondary alcohol
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020079 )

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	1.55	ALOGPS
logP	1.42	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.25 m³·mol⁻¹	ChemAxon
Polarizability	31.51 Å³	ChemAxon
Number of Rings	4	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

C00009318

Chemspider ID

10290195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14889248

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dryopterin (NP0056442)

MOL for NP0056442 (Dryopterin)

3D MOL for NP0056442 (Dryopterin)

3D SDF for NP0056442 (Dryopterin)

3D-SDF for NP0056442 (Dryopterin)

PDB for NP0056442 (Dryopterin)

3D PDB for NP0056442 (Dryopterin)

SMILES for NP0056442 (Dryopterin)

INCHI for NP0056442 (Dryopterin)

Structure for NP0056442 (Dryopterin)

3D Structure for NP0056442 (Dryopterin)