NP-MRD: Showing NP-Card for 3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein (NP0012435)

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Record Information

Version

2.0

Created at

2021-01-05 21:49:02 UTC

Updated at

2021-07-15 17:11:45 UTC

NP-MRD ID

NP0012435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein

Provided By

NPAtlas

Description

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein is found in Xylaria sp. cfcc 87468. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117083D          

 50 52  0  0  0  0            999 V2000
    5.6240    1.3273   -2.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    1.8130   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    2.9963   -1.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    1.0249   -0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    1.4838    0.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4186    0.3970    0.7691 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5191    0.0328   -0.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.9384    0.1966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6683   -0.3844    0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -0.7826   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -1.8619   -1.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768   -2.1716   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -1.4221   -2.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1667   -1.7297   -2.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.3400   -1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.0044   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062    1.1686    0.3675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2946    1.3665    0.9080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3566    2.5821    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.5700   -0.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    0.4982   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.2010   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294   -1.4189    1.6094 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2122   -0.5606    2.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.7208    1.9355 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5822   -3.0644    1.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -0.8221    1.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3316   -0.4938    1.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832    0.5547   -3.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6050    0.8697   -2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730    2.1541   -3.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    2.3791   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822    1.8156    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.7891    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8343   -2.4746   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -3.0381   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835   -2.5174   -3.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439    2.1053   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    1.0718    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977    0.4719    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9451    3.3814    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9159    2.3252    2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2619   -2.3926    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -0.9834    3.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067   -1.4754    3.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -3.3202    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5452   -1.3844    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -0.2809    1.2664 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 34  1  1  0  0  0
  8 35  1  6  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
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 23 45  1  6  0  0  0
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 26 48  1  0  0  0  0
 27 49  1  6  0  0  0
 28 50  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    5.6240    1.3273   -2.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    1.8130   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    2.9963   -1.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    1.0249   -0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    1.4838    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    0.3970    0.7691 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5191    0.0328   -0.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1667   -1.7297   -2.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.3400   -1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9062    1.1686    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    1.3665    0.9080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3566    2.5821    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.5700   -0.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    0.4982   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.2010   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294   -1.4189    1.6094 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2122   -0.5606    2.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.7208    1.9355 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5822   -3.0644    1.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -0.8221    1.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3316   -0.4938    1.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6899    2.3791   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  2  0
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M  END


  Mrv1652306242117083D          

 50 52  0  0  0  0            999 V2000
    5.6240    1.3273   -2.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    1.8130   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    2.9963   -1.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    1.0249   -0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    1.4838    0.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4186    0.3970    0.7691 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5191    0.0328   -0.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.9384    0.1966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6683   -0.3844    0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -0.7826   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -1.8619   -1.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768   -2.1716   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -1.4221   -2.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1667   -1.7297   -2.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.3400   -1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.0044   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1390    1.5700   -0.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    0.4982   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.2010   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2122   -0.5606    2.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9205    0.7891    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706   -1.8190   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8343   -2.4746   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6439    2.1053   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    1.0718    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977    0.4719    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602    3.0221    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    3.3814    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9159    2.3252    2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2619   -2.3926    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -0.9834    3.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067   -1.4754    3.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -3.3202    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5452   -1.3844    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -0.2809    1.2664 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27  6  1  0  0  0  0
 16 10  1  0  0  0  0
 21 15  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 34  1  1  0  0  0
  8 35  1  6  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
 14 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  1  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 23 45  1  6  0  0  0
 24 46  1  0  0  0  0
 25 47  1  1  0  0  0
 26 48  1  0  0  0  0
 27 49  1  6  0  0  0
 28 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0012435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(O[C@@]2([H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C2=C1C(=O)O[C@]([H])(C([H])([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O10/c1-7-5-9-11(4-3-10(20)13(9)17(24)26-7)27-18-16(23)15(22)14(21)12(28-18)6-25-8(2)19/h3-4,7,12,14-16,18,20-23H,5-6H2,1-2H3/t7-,12-,14-,15+,16-,18+/m1/s1

> <INCHI_KEY>
WMCJBKAMWFRRDO-PQJUGTJMSA-N

> <FORMULA>
C18H22O10

> <MOLECULAR_WEIGHT>
398.364

> <EXACT_MASS>
398.121296908

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.165319340738556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
0.4491129846666665

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.203940573356602

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.958830561922792

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102816960146

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
91.06940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    5.6240    1.3273   -2.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    1.8130   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    2.9963   -1.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    1.0249   -0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    1.4838    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    0.3970    0.7691 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5191    0.0328   -0.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.9384    0.1966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6683   -0.3844    0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -0.7826   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -1.8619   -1.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768   -2.1716   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -1.4221   -2.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1667   -1.7297   -2.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.3400   -1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.0044   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062    1.1686    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    1.3665    0.9080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3566    2.5821    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.5700   -0.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    0.4982   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.2010   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294   -1.4189    1.6094 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2122   -0.5606    2.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.7208    1.9355 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5822   -3.0644    1.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -0.8221    1.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3316   -0.4938    1.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832    0.5547   -3.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6050    0.8697   -2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730    2.1541   -3.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    2.3791   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822    1.8156    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.7891    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706   -1.8190   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8343   -2.4746   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -3.0381   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835   -2.5174   -3.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439    2.1053   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    1.0718    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977    0.4719    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602    3.0221    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    3.3814    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9159    2.3252    2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2619   -2.3926    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -0.9834    3.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067   -1.4754    3.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -3.3202    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5452   -1.3844    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -0.2809    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
  8 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27  6  1  0
 16 10  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  1
  8 35  1  6
 11 36  1  0
 12 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  1
 19 42  1  0
 19 43  1  0
 19 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  1
 26 48  1  0
 27 49  1  6
 28 50  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.624   1.327  -2.853  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.884   1.813  -1.642  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.086   2.996  -1.269  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.010   1.025  -0.940  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.308   1.484   0.207  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.419   0.397   0.769  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.519   0.033  -0.193  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.609  -0.938   0.197  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.668  -0.384   0.095  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.725  -0.783  -0.663  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.729  -1.862  -1.514  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.877  -2.172  -2.240  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.026  -1.422  -2.134  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.167  -1.730  -2.856  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.005  -0.340  -1.274  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.890  -0.004  -0.541  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.906   1.169   0.368  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.295   1.367   0.908  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.357   2.582   1.811  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.139   1.570  -0.236  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.201   0.498  -1.112  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.228   0.201  -1.778  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.829  -1.419   1.609  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.212  -0.561   2.521  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.250  -1.721   1.936  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.582  -3.064   1.804  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.205  -0.822   1.180  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.332  -0.494   1.930  0.00  0.00           O+0
HETATM   29  H   UNK     0       4.983   0.555  -3.334  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.605   0.870  -2.532  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.873   2.154  -3.538  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.690   2.379  -0.009  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.082   1.816   0.933  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.921   0.789   1.674  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.671  -1.819  -0.470  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.834  -2.475  -1.619  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.812  -3.038  -2.894  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.184  -2.517  -3.483  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.644   2.105  -0.200  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.146   1.072   1.178  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.598   0.472   1.479  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.360   3.022   2.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.945   3.381   1.290  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.916   2.325   2.718  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.262  -2.393   1.690  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.362  -0.983   3.424  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.407  -1.475   3.027  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.319  -3.320   2.433  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.545  -1.384   0.266  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.062  -0.281   1.266  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32   33                                             
CONECT    6    5    7   27   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   23   35                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   36                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   38                                                       
CONECT   15   13   16   21                                                  
CONECT   16   15   17   10                                                  
CONECT   17   16   18   39   40                                             
CONECT   18   17   19   20   41                                             
CONECT   19   18   42   43   44                                             
CONECT   20   18   21                                                       
CONECT   21   20   22   15                                                  
CONECT   22   21                                                            
CONECT   23    8   24   25   45                                             
CONECT   24   23   46                                                       
CONECT   25   23   26   27   47                                             
CONECT   26   25   48                                                       
CONECT   27   25   28    6   49                                             
CONECT   28   27   50                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   28                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    5.6240    1.3273   -2.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    1.8130   -1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    2.9963   -1.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    1.0249   -0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    1.4838    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    0.3970    0.7691 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5191    0.0328   -0.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.9384    0.1966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6683   -0.3844    0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -0.7826   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -1.8619   -1.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768   -2.1716   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -1.4221   -2.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1667   -1.7297   -2.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.3400   -1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.0044   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062    1.1686    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    1.3665    0.9080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3566    2.5821    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.5700   -0.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    0.4982   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.2010   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294   -1.4189    1.6094 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2122   -0.5606    2.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.7208    1.9355 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5822   -3.0644    1.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -0.8221    1.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3316   -0.4938    1.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832    0.5547   -3.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6050    0.8697   -2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730    2.1541   -3.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    2.3791   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822    1.8156    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.7891    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706   -1.8190   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8343   -2.4746   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -3.0381   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835   -2.5174   -3.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439    2.1053   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    1.0718    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977    0.4719    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602    3.0221    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    3.3814    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9159    2.3252    2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2619   -2.3926    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -0.9834    3.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067   -1.4754    3.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -3.3202    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5452   -1.3844    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -0.2809    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
  8 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27  6  1  0
 16 10  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  1
  8 35  1  6
 11 36  1  0
 12 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  1
 19 42  1  0
 19 43  1  0
 19 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  1
 26 48  1  0
 27 49  1  6
 28 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[(2R,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetic acid	Generator
3R-(+)-5-O-[6'-O-Acetyl]-a-D-glucopyranosyl-5-hydroxymellein	Generator
3R-(+)-5-O-[6'-O-Acetyl]-α-D-glucopyranosyl-5-hydroxymellein	Generator

Chemical Formula

C₁₈H₂₂O₁₀

Average Mass

398.3640 Da

Monoisotopic Mass

398.12130 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC2=C(O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C18H22O10/c1-7-5-9-11(4-3-10(20)13(9)17(24)26-7)27-18-16(23)15(22)14(21)12(28-18)6-25-8(2)19/h3-4,7,12,14-16,18,20-23H,5-6H2,1-2H3/t7-,12-,14-,15+,16-,18+/m1/s1

InChI Key

WMCJBKAMWFRRDO-PQJUGTJMSA-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
Xylaria sp. cfcc 87468	NPAtlas	24448065

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Benzopyran
Isochromane
2-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Carbonyl group
Alcohol
Organic oxide
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	-0.24	ALOGPS
logP	0.45	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	39.17 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

NPAtlas ID

NPA000023

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101904450

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein (NP0012435)

MOL for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

3D MOL for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

3D SDF for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

3D-SDF for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

PDB for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

3D PDB for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

SMILES for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

INCHI for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

Structure for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)

3D Structure for NP0012435 (3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein)