NP-MRD: Showing NP-Card for 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+ (NP0031508)

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Record Information

Version

2.0

Created at

2021-06-19 22:34:18 UTC

Updated at

2021-06-30 00:00:08 UTC

NP-MRD ID

NP0031508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+

Provided By

JEOL Database JEOL Logo

Description

(2R)-4-Hydroxy-7-chloro-2alpha-(beta-D-glucopyranosyloxy)-2H-1,4-benzoxazine-3(4H)-one belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+ is found in Acanthus ebracteatus. 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+ was first documented in 2001 (Kanchanapoom, T., et al.). Based on a literature review very few articles have been published on (2R)-4-Hydroxy-7-chloro-2alpha-(beta-D-glucopyranosyloxy)-2H-1,4-benzoxazine-3(4H)-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100343D          

 41 43  0  0  0  0            999 V2000
   -3.8191   -0.5764    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.1749    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -1.4873   -0.3667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1979   -1.5499    0.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -0.2676    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2029    0.2184    0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    1.5056    0.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6351    1.9621   -0.6846 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8610    1.9689   -1.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    1.4203    1.7864 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0494    2.7049    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.8568    2.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4845    0.6641    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.4611    2.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8966    3.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -2.6930   -1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -2.9211   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6071   -3.7872   -3.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -4.1020   -4.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -5.1608   -5.3255 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -3.5704   -3.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839   -2.7179   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055   -2.3890   -1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -1.5708   -0.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -1.2367   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.6669   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.4319    1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    2.2187    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0284    2.9702   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    1.2755   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    1.0702   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361    0.7691    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    2.5869    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    1.5855    3.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.1533    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -1.2366    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -1.6450    3.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -4.2130   -3.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6343   -3.8217   -4.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1922   -2.3188   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7715   -0.8565    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0  0  0  0
  6  7  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 10  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 23  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14  5  1  0  0  0  0
 10 11  1  0  0  0  0
 17 16  1  0  0  0  0
 23 24  1  0  0  0  0
 24  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3 16  1  0  0  0  0
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  3  4  1  0  0  0  0
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 24 25  1  0  0  0  0
 12 13  1  0  0  0  0
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 21 39  1  0  0  0  0
 22 40  1  0  0  0  0
 18 38  1  0  0  0  0
  3 26  1  6  0  0  0
  9 31  1  0  0  0  0
 25 41  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.8191   -0.5764    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.1749    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -1.4873   -0.3667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1979   -1.5499    0.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -0.2676    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2029    0.2184    0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    1.5056    0.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6351    1.9621   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    1.9689   -1.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    1.4203    1.7864 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0494    2.7049    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.8568    2.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4845    0.6641    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.4611    2.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8966    3.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -2.6930   -1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -2.9211   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6071   -3.7872   -3.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -4.1020   -4.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -5.1608   -5.3255 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -3.5704   -3.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839   -2.7179   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055   -2.3890   -1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -1.5708   -0.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -1.2367   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.6669   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.4319    1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    2.2187    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0284    2.9702   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    1.2755   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    1.0702   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361    0.7691    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    2.5869    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    1.5855    3.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.1533    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -1.2366    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -1.6450    3.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -4.2130   -3.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6343   -3.8217   -4.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1922   -2.3188   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7715   -0.8565    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0
  6  7  1  0
 21 22  1  0
 22 23  2  0
  7 10  1  0
 17 18  2  0
 18 19  1  0
 17 23  1  0
 10 12  1  0
 12 14  1  0
 14  5  1  0
 10 11  1  0
 17 16  1  0
 23 24  1  0
 24  2  1  0
  2  3  1  0
  3 16  1  0
  7  8  1  0
 19 20  1  0
  2  1  2  0
  3  4  1  0
  8  9  1  0
  5  6  1  0
 24 25  1  0
 12 13  1  0
 14 15  1  0
  5  4  1  0
  5 27  1  1
 10 32  1  6
 11 33  1  0
 15 37  1  0
 14 36  1  6
  7 28  1  1
  8 29  1  0
  8 30  1  0
 13 35  1  0
 12 34  1  1
 21 39  1  0
 22 40  1  0
 18 38  1  0
  3 26  1  6
  9 31  1  0
 25 41  1  0
M  END


  Mrv1652306202100343D          

 41 43  0  0  0  0            999 V2000
   -3.8191   -0.5764    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.1749    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -1.4873   -0.3667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1979   -1.5499    0.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -0.2676    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2029    0.2184    0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    1.5056    0.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6351    1.9621   -0.6846 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8610    1.9689   -1.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    1.4203    1.7864 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0494    2.7049    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.8568    2.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4845    0.6641    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.4611    2.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8966    3.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -2.6930   -1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -2.9211   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6071   -3.7872   -3.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -4.1020   -4.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -5.1608   -5.3255 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -3.5704   -3.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839   -2.7179   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055   -2.3890   -1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -1.5708   -0.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -1.2367   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5298    0.4319    1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    2.2187    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4735    1.2755   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    1.0702   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361    0.7691    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    2.5869    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    1.5855    3.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.1533    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -1.2366    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -1.6450    3.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -4.2130   -3.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6343   -3.8217   -4.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1922   -2.3188   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7715   -0.8565    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0  0  0  0
  6  7  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
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 10 12  1  0  0  0  0
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 14  5  1  0  0  0  0
 10 11  1  0  0  0  0
 17 16  1  0  0  0  0
 23 24  1  0  0  0  0
 24  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3 16  1  0  0  0  0
  7  8  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  2  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
 24 25  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
  5  4  1  0  0  0  0
  5 27  1  1  0  0  0
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 15 37  1  0  0  0  0
 14 36  1  6  0  0  0
  7 28  1  1  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 13 35  1  0  0  0  0
 12 34  1  1  0  0  0
 21 39  1  0  0  0  0
 22 40  1  0  0  0  0
 18 38  1  0  0  0  0
  3 26  1  6  0  0  0
  9 31  1  0  0  0  0
 25 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]ON1C(=O)[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])OC2=C([H])C(Cl)=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H16ClNO9/c15-5-1-2-6-7(3-5)23-14(12(21)16(6)22)25-13-11(20)10(19)9(18)8(4-17)24-13/h1-3,8-11,13-14,17-20,22H,4H2/t8-,9-,10+,11-,13+,14-/m1/s1

> <INCHI_KEY>
XEGGMKDQOCMCAD-TWTZXXGESA-N

> <FORMULA>
C14H16ClNO9

> <MOLECULAR_WEIGHT>
377.73

> <EXACT_MASS>
377.0513588

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.63029008945586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-7-chloro-4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1,4-benzoxazin-3-one

> <ALOGPS_LOGP>
-0.72

> <JCHEM_LOGP>
-1.0637084403333334

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20716291384814

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.774506961758018

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849224353024

> <JCHEM_POLAR_SURFACE_AREA>
149.15

> <JCHEM_REFRACTIVITY>
79.22540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-7-chloro-4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1,4-benzoxazin-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.8191   -0.5764    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.1749    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -1.4873   -0.3667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1979   -1.5499    0.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -0.2676    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2029    0.2184    0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    1.5056    0.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6351    1.9621   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    1.9689   -1.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    1.4203    1.7864 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0494    2.7049    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.8568    2.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4845    0.6641    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.4611    2.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8966    3.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -2.6930   -1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -2.9211   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6071   -3.7872   -3.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -4.1020   -4.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -5.1608   -5.3255 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -3.5704   -3.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839   -2.7179   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055   -2.3890   -1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -1.5708   -0.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -1.2367   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.6669   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.4319    1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    2.2187    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0284    2.9702   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    1.2755   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    1.0702   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361    0.7691    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    2.5869    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    1.5855    3.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.1533    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -1.2366    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -1.6450    3.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -4.2130   -3.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6343   -3.8217   -4.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1922   -2.3188   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7715   -0.8565    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0
  6  7  1  0
 21 22  1  0
 22 23  2  0
  7 10  1  0
 17 18  2  0
 18 19  1  0
 17 23  1  0
 10 12  1  0
 12 14  1  0
 14  5  1  0
 10 11  1  0
 17 16  1  0
 23 24  1  0
 24  2  1  0
  2  3  1  0
  3 16  1  0
  7  8  1  0
 19 20  1  0
  2  1  2  0
  3  4  1  0
  8  9  1  0
  5  6  1  0
 24 25  1  0
 12 13  1  0
 14 15  1  0
  5  4  1  0
  5 27  1  1
 10 32  1  6
 11 33  1  0
 15 37  1  0
 14 36  1  6
  7 28  1  1
  8 29  1  0
  8 30  1  0
 13 35  1  0
 12 34  1  1
 21 39  1  0
 22 40  1  0
 18 38  1  0
  3 26  1  6
  9 31  1  0
 25 41  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      -3.819  -0.576   1.133  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.531  -1.175   0.094  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.083  -1.487  -0.367  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.198  -1.550   0.754  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.695  -0.268   1.136  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.203   0.218   0.138  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.756   1.506   0.485  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.635   1.962  -0.685  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.861   1.969  -1.887  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.563   1.420   1.786  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.049   2.705   2.176  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.682   0.857   2.903  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.484   0.664   4.079  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.043  -0.461   2.474  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.844  -0.897   3.516  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.924  -2.693  -1.117  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.916  -2.921  -2.034  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.607  -3.787  -3.082  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.585  -4.102  -4.023  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -3.208  -5.161  -5.325  0.00  0.00          Cl+0
HETATM   21  C   UNK     0      -4.870  -3.570  -3.915  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.184  -2.718  -2.853  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.205  -2.389  -1.910  0.00  0.00           C+0
HETATM   24  N   UNK     0      -4.481  -1.571  -0.812  0.00  0.00           N+0
HETATM   25  O   UNK     0      -5.827  -1.237  -0.554  0.00  0.00           O+0
HETATM   26  H   UNK     0      -1.783  -0.667  -1.034  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.530   0.432   1.265  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.073   2.219   0.582  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.028   2.970  -0.525  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.474   1.276  -0.842  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.489   1.070  -1.960  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.436   0.769   1.652  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.390   2.587   3.087  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.087   1.585   3.187  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.917   0.153   4.692  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.813  -1.237   2.379  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.350  -1.645   3.141  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.610  -4.213  -3.159  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.634  -3.822  -4.647  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.192  -2.319  -2.769  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.771  -0.857   0.348  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   24    3    1                                                  
CONECT    3    2   16    4   26                                             
CONECT    4    3    5                                                       
CONECT    5   14    6    4   27                                             
CONECT    6    7    5                                                       
CONECT    7    6   10    8   28                                             
CONECT    8    7    9   29   30                                             
CONECT    9    8   31                                                       
CONECT   10    7   12   11   32                                             
CONECT   11   10   33                                                       
CONECT   12   10   14   13   34                                             
CONECT   13   12   35                                                       
CONECT   14   12    5   15   36                                             
CONECT   15   14   37                                                       
CONECT   16   17    3                                                       
CONECT   17   18   23   16                                                  
CONECT   18   17   19   38                                                  
CONECT   19   21   18   20                                                  
CONECT   20   19                                                            
CONECT   21   19   22   39                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   17   24                                                  
CONECT   24   23    2   25                                                  
CONECT   25   24   41                                                       
CONECT   26    3                                                            
CONECT   27    5                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   18                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
CONECT   41   25                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
   -3.8191   -0.5764    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.1749    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -1.4873   -0.3667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1979   -1.5499    0.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -0.2676    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2029    0.2184    0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    1.5056    0.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6351    1.9621   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    1.9689   -1.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    1.4203    1.7864 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0494    2.7049    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.8568    2.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4845    0.6641    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.4611    2.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8966    3.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -2.6930   -1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -2.9211   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6071   -3.7872   -3.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -4.1020   -4.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -5.1608   -5.3255 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -3.5704   -3.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839   -2.7179   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055   -2.3890   -1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -1.5708   -0.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -1.2367   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.6669   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.4319    1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    2.2187    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0284    2.9702   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    1.2755   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    1.0702   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361    0.7691    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    2.5869    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    1.5855    3.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    0.1533    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -1.2366    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -1.6450    3.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -4.2130   -3.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6343   -3.8217   -4.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1922   -2.3188   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7715   -0.8565    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0
  6  7  1  0
 21 22  1  0
 22 23  2  0
  7 10  1  0
 17 18  2  0
 18 19  1  0
 17 23  1  0
 10 12  1  0
 12 14  1  0
 14  5  1  0
 10 11  1  0
 17 16  1  0
 23 24  1  0
 24  2  1  0
  2  3  1  0
  3 16  1  0
  7  8  1  0
 19 20  1  0
  2  1  2  0
  3  4  1  0
  8  9  1  0
  5  6  1  0
 24 25  1  0
 12 13  1  0
 14 15  1  0
  5  4  1  0
  5 27  1  1
 10 32  1  6
 11 33  1  0
 15 37  1  0
 14 36  1  6
  7 28  1  1
  8 29  1  0
  8 30  1  0
 13 35  1  0
 12 34  1  1
 21 39  1  0
 22 40  1  0
 18 38  1  0
  3 26  1  6
  9 31  1  0
 25 41  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2R)-4-Hydroxy-7-chloro-2a-(b-D-glucopyranosyloxy)-2H-1,4-benzoxazine-3(4H)-one	Generator
(2R)-4-Hydroxy-7-chloro-2α-(β-D-glucopyranosyloxy)-2H-1,4-benzoxazine-3(4H)-one	Generator

Chemical Formula

C₁₄H₁₆ClNO₉

Average Mass

377.7300 Da

Monoisotopic Mass

377.05136 Da

IUPAC Name

(2R)-7-chloro-4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1,4-benzoxazin-3-one

Traditional Name

(2R)-7-chloro-4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1,4-benzoxazin-3-one

CAS Registry Number

Not Available

SMILES

[H]ON1C(=O)[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])OC2=C([H])C(Cl)=C([H])C([H])=C12

InChI Identifier

InChI=1S/C14H16ClNO9/c15-5-1-2-6-7(3-5)23-14(12(21)16(6)22)25-13-11(20)10(19)9(18)8(4-17)24-13/h1-3,8-11,13-14,17-20,22H,4H2/t8-,9-,10+,11-,13+,14-/m1/s1

InChI Key

XEGGMKDQOCMCAD-TWTZXXGESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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
Acanthus ebracteatus	JEOL database	Kanchanapoom, T., et al, Phytochemistry 58, 811 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
Benzoxazinone
O-glycosyl compound
Benzomorpholine
Benzoxazine
Aryl chloride
Aryl halide
Monosaccharide
Oxane
Oxazinane
Benzenoid
Secondary alcohol
Hydroxamic acid
Azacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Oxacycle
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Primary alcohol
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
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	-0.72	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.23 m³·mol⁻¹	ChemAxon
Polarizability	34.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

102376768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kanchanapoom, T., et al. (2001). Kanchanapoom, T., et al, Phytochemistry 58, 811 (2001) . Phytochem..

Showing NP-Card for 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+ (NP0031508)

MOL for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

3D MOL for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

3D SDF for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

3D-SDF for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

PDB for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

3D PDB for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

SMILES for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

INCHI for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

Structure for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)

3D Structure for NP0031508 ( 7-chloro-(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H+)