NP-MRD: Showing NP-Card for (2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol (NP0298026)

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Record Information

Version

2.0

Created at

2022-09-10 08:54:43 UTC

Updated at

2022-09-10 08:54:43 UTC

NP-MRD ID

NP0298026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

Description

(2S,3R)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol 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. (2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol is found in Geranium pratense. Based on a literature review very few articles have been published on (2S,3R)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.8530    0.9659    0.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4983    0.6403   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0222   -0.6110    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -0.9111    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913    0.0550   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -0.2294   -0.4013 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4202    0.8012    0.2105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7785    0.6262    0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468    1.7164    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043    1.5917    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316    2.6745    0.6044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5163    0.3182    0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2567    0.0339    0.7131 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.8007    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313   -2.0910    0.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277   -0.6187    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -1.8243    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -1.5747    0.0691 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4691   -2.5806   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455    1.3213   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5785    1.6083   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    2.9045   -0.7589 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4854    0.2269    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7053   -1.3941    0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746   -1.9485    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1087   -0.1723   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    2.7018    0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5591    3.6329    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -2.8818    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101   -2.3635    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -2.5289   -0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5049   -1.7636    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359   -2.7060   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    2.0794   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873    3.1016   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 21  1  0
 21 22  1  0
 21 20  2  0
  6 18  1  0
 20  5  1  0
  8 16  1  0
 19 33  1  0
 18 32  1  1
 17 30  1  0
 17 31  1  0
 15 29  1  0
 11 28  1  0
  9 27  1  0
  6 26  1  6
  4 25  1  0
  3 24  1  0
  1 23  1  0
 22 35  1  0
 20 34  1  0
M  END


  Mrv1652309102210542D          

 22 24  0  0  1  0            999 V2000
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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    0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  2  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 Cl  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
    2.8579   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  1  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC2=C(O)C(Cl)=C(O)C=C2O[C@H]1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13ClO6/c16-13-10(19)5-12-7(14(13)21)4-11(20)15(22-12)6-1-2-8(17)9(18)3-6/h1-3,5,11,15,17-21H,4H2/t11-,15+/m1/s1

> <INCHI_KEY>
BHTBHJNGFQRAJI-ABAIWWIYSA-N

> <FORMULA>
C15H13ClO6

> <MOLECULAR_WEIGHT>
324.71

> <EXACT_MASS>
324.0400658

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.676814657199188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <JCHEM_LOGP>
2.3991516916666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.92602568894605

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.9485591411145435

> <JCHEM_PKA_STRONGEST_BASIC>
-3.295571119368482

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
78.8045

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       8.002  -3.080   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18                                                            
CONECT   20    5   21                                                       
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃ClO₆

Average Mass

324.7100 Da

Monoisotopic Mass

324.04007 Da

IUPAC Name

(2S,3R)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

(2S,3R)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(O)C(Cl)=C(O)C=C2O[C@H]1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H13ClO6/c16-13-10(19)5-12-7(14(13)21)4-11(20)15(22-12)6-1-2-8(17)9(18)3-6/h1-3,5,11,15,17-21H,4H2/t11-,15+/m1/s1

InChI Key

BHTBHJNGFQRAJI-ABAIWWIYSA-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
Geranium pratense	LOTUS Database	35616633

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
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
1-benzopyran
Benzopyran
Chromane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alcohol
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	2.4	ChemAxon
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.8 m³·mol⁻¹	ChemAxon
Polarizability	30.68 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

162911200

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol (NP0298026)

MOL for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D MOL for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D SDF for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D-SDF for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

PDB for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D PDB for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

SMILES for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

INCHI for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

Structure for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D Structure for NP0298026 ((2s,3r)-6-chloro-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)