NP-MRD: Showing NP-Card for 6-chlorocatechin (NP0031718)

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Record Information

Version

2.0

Created at

2021-06-19 22:43:21 UTC

Updated at

2021-06-30 00:00:28 UTC

NP-MRD ID

NP0031718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-chlorocatechin

Provided By

JEOL Database JEOL Logo

Description

(-)-6-Chloroepicatechin 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. 6-chlorocatechin is found in Geranium pratense, Geranium pratense subsp.finitimum (Woronow) Knuth and Rumex patientia. 6-chlorocatechin was first documented in 2007 (PMID: 17904777). Based on a literature review very few articles have been published on (-)-6-chloroepicatechin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100433D          

 35 37  0  0  0  0            999 V2000
    2.7080   -3.6906    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -2.8423   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -2.8746   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -2.0065   -2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.1041   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.1404   -1.5772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4198   -0.0934   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    0.8965   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.7559    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    1.7117    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    1.5197    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    2.8130   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6395    3.9939   -0.8358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    2.9554   -1.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0875    4.0262   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    2.0081   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    2.1623   -2.3520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8393    1.2533   -1.8800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1570    1.2188   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -1.0868    0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -1.9597    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -1.9854    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -3.4944    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -3.5699   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178   -2.0359   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950   -0.5619   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.1036    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063    2.2602    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    4.5789   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151    3.1995   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.9331   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    1.6849   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    0.7225   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886   -0.3957    0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -1.3683    2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 16  2  0  0  0  0
 10 11  1  0  0  0  0
 14 12  2  0  0  0  0
 12 13  1  0  0  0  0
 16 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 10  1  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
 10  9  2  0  0  0  0
  5  4  2  0  0  0  0
  9  8  1  0  0  0  0
  4  3  1  0  0  0  0
  8  7  1  0  0  0  0
  3  2  2  0  0  0  0
 16 17  1  0  0  0  0
  2 21  1  0  0  0  0
 17 18  1  0  0  0  0
 21 20  2  0  0  0  0
 20  5  1  0  0  0  0
 18  6  1  0  0  0  0
 21 22  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  9 27  1  0  0  0  0
 17 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  1  0  0  0
  6 26  1  6  0  0  0
 11 28  1  0  0  0  0
 15 29  1  0  0  0  0
 19 33  1  0  0  0  0
  4 25  1  0  0  0  0
  3 24  1  0  0  0  0
 20 34  1  0  0  0  0
 22 35  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.7080   -3.6906    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -2.8423   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -2.8746   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -2.0065   -2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.1041   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.1404   -1.5772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4198   -0.0934   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    0.8965   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.7559    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    1.7117    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    1.5197    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    2.8130   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6395    3.9939   -0.8358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    2.9554   -1.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0875    4.0262   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    2.0081   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    2.1623   -2.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.2533   -1.8800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1570    1.2188   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -1.0868    0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -1.9597    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -1.9854    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -3.4944    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -3.5699   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178   -2.0359   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950   -0.5619   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.1036    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063    2.2602    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    4.5789   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151    3.1995   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.9331   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    1.6849   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    0.7225   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886   -0.3957    0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -1.3683    2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 16  2  0
 10 11  1  0
 14 12  2  0
 12 13  1  0
 16 14  1  0
 14 15  1  0
 12 10  1  0
 18 19  1  0
  6  5  1  0
 10  9  2  0
  5  4  2  0
  9  8  1  0
  4  3  1  0
  8  7  1  0
  3  2  2  0
 16 17  1  0
  2 21  1  0
 17 18  1  0
 21 20  2  0
 20  5  1  0
 18  6  1  0
 21 22  1  0
  6  7  1  0
  2  1  1  0
  9 27  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  1
  6 26  1  6
 11 28  1  0
 15 29  1  0
 19 33  1  0
  4 25  1  0
  3 24  1  0
 20 34  1  0
 22 35  1  0
  1 23  1  0
M  END


  Mrv1652306202100433D          

 35 37  0  0  0  0            999 V2000
    2.7080   -3.6906    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -2.8423   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -2.8746   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -2.0065   -2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.1041   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.1404   -1.5772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4198   -0.0934   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    0.8965   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.7559    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    1.7117    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    1.5197    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    2.8130   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6395    3.9939   -0.8358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    2.9554   -1.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0875    4.0262   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    2.0081   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    2.1623   -2.3520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8393    1.2533   -1.8800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1570    1.2188   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -1.0868    0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -1.9597    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -1.9854    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -3.4944    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -3.5699   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178   -2.0359   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950   -0.5619   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.1036    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063    2.2602    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    4.5789   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151    3.1995   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.9331   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    1.6849   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    0.7225   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886   -0.3957    0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -1.3683    2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 16  2  0  0  0  0
 10 11  1  0  0  0  0
 14 12  2  0  0  0  0
 12 13  1  0  0  0  0
 16 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 10  1  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
 10  9  2  0  0  0  0
  5  4  2  0  0  0  0
  9  8  1  0  0  0  0
  4  3  1  0  0  0  0
  8  7  1  0  0  0  0
  3  2  2  0  0  0  0
 16 17  1  0  0  0  0
  2 21  1  0  0  0  0
 17 18  1  0  0  0  0
 21 20  2  0  0  0  0
 20  5  1  0  0  0  0
 18  6  1  0  0  0  0
 21 22  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  9 27  1  0  0  0  0
 17 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  1  0  0  0
  6 26  1  6  0  0  0
 11 28  1  0  0  0  0
 15 29  1  0  0  0  0
 19 33  1  0  0  0  0
  4 25  1  0  0  0  0
  3 24  1  0  0  0  0
 20 34  1  0  0  0  0
 22 35  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1O[H])[C@@]1([H])OC2=C(C(O[H])=C(Cl)C(O[H])=C2[H])C([H])([H])[C@]1([H])O[H]

> <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+/m0/s1

> <INCHI_KEY>
BHTBHJNGFQRAJI-XHDPSFHLSA-N

> <FORMULA>
C15H13ClO6

> <MOLECULAR_WEIGHT>
324.71

> <EXACT_MASS>
324.0400658

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
31.36473615325625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
2.3991516916666664

> <ALOGPS_LOGS>
-3.17

> <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

> <ALOGPS_SOLUBILITY>
2.20e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.7080   -3.6906    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -2.8423   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -2.8746   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -2.0065   -2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.1041   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.1404   -1.5772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4198   -0.0934   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    0.8965   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.7559    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    1.7117    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    1.5197    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    2.8130   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6395    3.9939   -0.8358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    2.9554   -1.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0875    4.0262   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    2.0081   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    2.1623   -2.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.2533   -1.8800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1570    1.2188   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -1.0868    0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -1.9597    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -1.9854    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -3.4944    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -3.5699   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178   -2.0359   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950   -0.5619   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.1036    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063    2.2602    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    4.5789   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151    3.1995   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.9331   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    1.6849   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    0.7225   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886   -0.3957    0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -1.3683    2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 16  2  0
 10 11  1  0
 14 12  2  0
 12 13  1  0
 16 14  1  0
 14 15  1  0
 12 10  1  0
 18 19  1  0
  6  5  1  0
 10  9  2  0
  5  4  2  0
  9  8  1  0
  4  3  1  0
  8  7  1  0
  3  2  2  0
 16 17  1  0
  2 21  1  0
 17 18  1  0
 21 20  2  0
 20  5  1  0
 18  6  1  0
 21 22  1  0
  6  7  1  0
  2  1  1  0
  9 27  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  1
  6 26  1  6
 11 28  1  0
 15 29  1  0
 19 33  1  0
  4 25  1  0
  3 24  1  0
 20 34  1  0
 22 35  1  0
  1 23  1  0
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       2.708  -3.691   0.039  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.708  -2.842  -0.341  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.254  -2.875  -1.650  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.232  -2.006  -2.039  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.336  -1.104  -1.119  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.425  -0.140  -1.577  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.420  -0.093  -0.542  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.355   0.897  -0.667  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.491   0.756   0.134  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.499   1.712   0.081  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.591   1.520   0.882  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.380   2.813  -0.766  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -6.640   3.994  -0.836  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      -4.234   2.955  -1.556  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.088   4.026  -2.400  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.202   2.008  -1.504  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.972   2.162  -2.352  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.839   1.253  -1.880  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.157   1.219  -2.908  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.142  -1.087   0.205  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.157  -1.960   0.583  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.648  -1.985   1.859  0.00  0.00           O+0
HETATM   23  H   UNK     0       2.848  -3.494   0.987  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.690  -3.570  -2.361  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.118  -2.036  -3.070  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.895  -0.562  -2.477  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.592  -0.104   0.791  0.00  0.00           H+0
HETATM   28  H   UNK     0      -7.206   2.260   0.726  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.888   4.579  -2.322  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.615   3.200  -2.337  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.229   1.933  -3.395  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.387   1.685  -0.977  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.919   0.723  -2.557  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.289  -0.396   0.924  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.123  -1.368   2.397  0.00  0.00           H+0
CONECT    1    2   23                                                       
CONECT    2    3   21    1                                                  
CONECT    3    4    2   24                                                  
CONECT    4    5    3   25                                                  
CONECT    5    6    4   20                                                  
CONECT    6    5   18    7   26                                             
CONECT    7    8    6                                                       
CONECT    8   16    9    7                                                  
CONECT    9   10    8   27                                                  
CONECT   10   11   12    9                                                  
CONECT   11   10   28                                                       
CONECT   12   14   13   10                                                  
CONECT   13   12                                                            
CONECT   14   12   16   15                                                  
CONECT   15   14   29                                                       
CONECT   16    8   14   17                                                  
CONECT   17   16   18   30   31                                             
CONECT   18   19   17    6   32                                             
CONECT   19   18   33                                                       
CONECT   20   21    5   34                                                  
CONECT   21    2   20   22                                                  
CONECT   22   21   35                                                       
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
CONECT   29   15                                                            
CONECT   30   17                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   22                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
    2.7080   -3.6906    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -2.8423   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -2.8746   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -2.0065   -2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.1041   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.1404   -1.5772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4198   -0.0934   -0.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    0.8965   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.7559    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    1.7117    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    1.5197    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    2.8130   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6395    3.9939   -0.8358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    2.9554   -1.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0875    4.0262   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    2.0081   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    2.1623   -2.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.2533   -1.8800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1570    1.2188   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -1.0868    0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -1.9597    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -1.9854    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -3.4944    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -3.5699   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178   -2.0359   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950   -0.5619   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.1036    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063    2.2602    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    4.5789   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151    3.1995   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.9331   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    1.6849   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    0.7225   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886   -0.3957    0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -1.3683    2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 16  2  0
 10 11  1  0
 14 12  2  0
 12 13  1  0
 16 14  1  0
 14 15  1  0
 12 10  1  0
 18 19  1  0
  6  5  1  0
 10  9  2  0
  5  4  2  0
  9  8  1  0
  4  3  1  0
  8  7  1  0
  3  2  2  0
 16 17  1  0
  2 21  1  0
 17 18  1  0
 21 20  2  0
 20  5  1  0
 18  6  1  0
 21 22  1  0
  6  7  1  0
  2  1  1  0
  9 27  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  1
  6 26  1  6
 11 28  1  0
 15 29  1  0
 19 33  1  0
  4 25  1  0
  3 24  1  0
 20 34  1  0
 22 35  1  0
  1 23  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃ClO₆

Average Mass

324.7100 Da

Monoisotopic Mass

324.04007 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1O[H])[C@@]1([H])OC2=C(C(O[H])=C(Cl)C(O[H])=C2[H])C([H])([H])[C@]1([H])O[H]

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+/m0/s1

InChI Key

BHTBHJNGFQRAJI-XHDPSFHLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Geranium pratense	LOTUS Database	35616633
Geranium pratense subsp.finitimum (Woronow) Knuth	Plant	KNApSAcK
Rumex patientia	JEOL database	Demirezer, L. O., et al, Phytochemistry 58, 1213 (2001)

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
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aryl chloride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organooxygen compound
Alcohol
Organic oxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
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	1.67	ALOGPS
logP	2.4	ChemAxon
logS	-3.2	ALOGPS
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	31.36 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

552384

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636642

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kupeli E, Tatli II, Akdemir ZS, Yesilada E: Estimation of antinociceptive and anti-inflammatory activity on Geranium pratense subsp. finitimum and its phenolic compounds. J Ethnopharmacol. 2007 Nov 1;114(2):234-40. doi: 10.1016/j.jep.2007.08.005. Epub 2007 Aug 10. [PubMed:17904777 ]
Demirezer, L. O., et al. (2001). Demirezer, L. O., et al, Phytochemistry 58, 1213 (2001) . Phytochem..

Showing NP-Card for 6-chlorocatechin (NP0031718)

MOL for NP0031718 ( 6-chlorocatechin)

3D MOL for NP0031718 ( 6-chlorocatechin)

3D SDF for NP0031718 ( 6-chlorocatechin)

3D-SDF for NP0031718 ( 6-chlorocatechin)

PDB for NP0031718 ( 6-chlorocatechin)

3D PDB for NP0031718 ( 6-chlorocatechin)

SMILES for NP0031718 ( 6-chlorocatechin)

INCHI for NP0031718 ( 6-chlorocatechin)

Structure for NP0031718 ( 6-chlorocatechin)

3D Structure for NP0031718 ( 6-chlorocatechin)