NP-MRD: Showing NP-Card for itoside L (NP0033753)

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Record Information

Version

2.0

Created at

2021-06-20 17:40:58 UTC

Updated at

2021-06-30 00:03:44 UTC

NP-MRD ID

NP0033753

Secondary Accession Numbers

None

Natural Product Identification

Common Name

itoside L

Provided By

JEOL Database JEOL Logo

Description

ITOSIDE L 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. itoside L is found in Itoa orientalis. itoside L was first documented in 2008 (Chai, X. Y., et al.). Based on a literature review very few articles have been published on ITOSIDE L.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119403D          

 40 41  0  0  0  0            999 V2000
    2.7160    0.4587    1.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6088    1.9897 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9339    1.8666    0.8486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1434    0.6734    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.7645   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4586   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7871   -1.4934   -1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7898   -2.5953   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -3.8954   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -4.3948   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1480   -5.5194   -1.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -3.3451   -1.0344 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4988   -1.9836   -0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3071   -2.0777    0.9039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    1.8908   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6630    2.0377   -1.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225    3.2086    0.0359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9443    4.2492    0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    3.0705    1.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7878    4.2772    1.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887   -0.2817    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965    2.4576    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003    1.4038    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    2.0241   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    0.9451   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -1.1185   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -2.3087   -1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -4.6427   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -4.7366    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -5.9156   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332   -3.2670   -2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -3.6861   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -1.2568   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.2927    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866    1.6671    0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.1593   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5518    3.5413   -0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    4.1858   -0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    2.9407    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260    4.9987    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 13  7  1  0  0  0  0
  5 15  1  0  0  0  0
 15 17  1  0  0  0  0
 17 19  1  0  0  0  0
 19  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 13 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 10 11  1  0  0  0  0
  7  6  1  0  0  0  0
 19 20  1  0  0  0  0
 13 14  1  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  1  6  0  0  0
 19 39  1  1  0  0  0
 20 40  1  0  0  0  0
 17 37  1  6  0  0  0
 18 38  1  0  0  0  0
 15 35  1  1  0  0  0
 16 36  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  6  0  0  0
  1 21  1  0  0  0  0
 13 33  1  1  0  0  0
  7 26  1  6  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  1  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 11 30  1  0  0  0  0
 14 34  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    2.7160    0.4587    1.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6088    1.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9339    1.8666    0.8486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1434    0.6734    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.7645   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4586   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7871   -1.4934   -1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7898   -2.5953   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -3.8954   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -4.3948   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1480   -5.5194   -1.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -3.3451   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -1.9836   -0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3071   -2.0777    0.9039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    1.8908   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6630    2.0377   -1.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225    3.2086    0.0359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9443    4.2492    0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    3.0705    1.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7878    4.2772    1.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887   -0.2817    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965    2.4576    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003    1.4038    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    2.0241   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    0.9451   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -1.1185   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -2.3087   -1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -4.6427   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -4.7366    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -5.9156   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332   -3.2670   -2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -3.6861   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -1.2568   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.2927    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866    1.6671    0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.1593   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5518    3.5413   -0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    4.1858   -0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    2.9407    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260    4.9987    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 15 16  1  0
  2  1  1  0
 13  7  1  0
  5 15  1  0
 15 17  1  0
 17 19  1  0
 19  3  1  0
  3  4  1  0
  4  5  1  0
 13 12  1  0
  8  9  2  0
  9 10  1  0
 10 12  1  0
 10 11  1  0
  7  6  1  0
 19 20  1  0
 13 14  1  0
  7  8  1  0
  3  2  1  0
  5  6  1  0
  5 25  1  6
 19 39  1  1
 20 40  1  0
 17 37  1  6
 18 38  1  0
 15 35  1  1
 16 36  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  6
  1 21  1  0
 13 33  1  1
  7 26  1  6
  8 27  1  0
  9 28  1  0
 10 29  1  1
 12 31  1  0
 12 32  1  0
 11 30  1  0
 14 34  1  0
M  END


  Mrv1652306202119403D          

 40 41  0  0  0  0            999 V2000
    2.7160    0.4587    1.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6088    1.9897 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9339    1.8666    0.8486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1434    0.6734    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.7645   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4586   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7871   -1.4934   -1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7898   -2.5953   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -3.8954   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -4.3948   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1480   -5.5194   -1.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -3.3451   -1.0344 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4988   -1.9836   -0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3071   -2.0777    0.9039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    1.8908   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6630    2.0377   -1.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225    3.2086    0.0359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9443    4.2492    0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    3.0705    1.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7878    4.2772    1.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887   -0.2817    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965    2.4576    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003    1.4038    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    2.0241   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    0.9451   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -1.1185   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -2.3087   -1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -4.6427   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -4.7366    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -5.9156   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332   -3.2670   -2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -3.6861   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -1.2568   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.2927    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866    1.6671    0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.1593   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5518    3.5413   -0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    4.1858   -0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    2.9407    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260    4.9987    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 13  7  1  0  0  0  0
  5 15  1  0  0  0  0
 15 17  1  0  0  0  0
 17 19  1  0  0  0  0
 19  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 13 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 10 11  1  0  0  0  0
  7  6  1  0  0  0  0
 19 20  1  0  0  0  0
 13 14  1  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  1  6  0  0  0
 19 39  1  1  0  0  0
 20 40  1  0  0  0  0
 17 37  1  6  0  0  0
 18 38  1  0  0  0  0
 15 35  1  1  0  0  0
 16 36  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  6  0  0  0
  1 21  1  0  0  0  0
 13 33  1  1  0  0  0
  7 26  1  6  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  1  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 11 30  1  0  0  0  0
 14 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])C([H])=C([H])[C@@]([H])(O[H])C([H])([H])[C@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O8/c13-4-8-9(16)10(17)11(18)12(20-8)19-7-2-1-5(14)3-6(7)15/h1-2,5-18H,3-4H2/t5-,6+,7-,8-,9-,10+,11-,12-/m1/s1

> <INCHI_KEY>
FSZLXNSBZLJIOC-VIXLETMSSA-N

> <FORMULA>
C12H20O8

> <MOLECULAR_WEIGHT>
292.284

> <EXACT_MASS>
292.115817604

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.332172229445053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,4S,6S)-4,6-dihydroxycyclohex-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.83

> <JCHEM_LOGP>
-3.0746650593333333

> <ALOGPS_LOGS>
-0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.139339044555314

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.202521670438617

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8863966692163032

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
65.48479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.45e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,4S,6S)-4,6-dihydroxycyclohex-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    2.7160    0.4587    1.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6088    1.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9339    1.8666    0.8486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1434    0.6734    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.7645   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4586   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7871   -1.4934   -1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7898   -2.5953   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -3.8954   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -4.3948   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1480   -5.5194   -1.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -3.3451   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -1.9836   -0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3071   -2.0777    0.9039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    1.8908   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6630    2.0377   -1.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225    3.2086    0.0359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9443    4.2492    0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    3.0705    1.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7878    4.2772    1.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887   -0.2817    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965    2.4576    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003    1.4038    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    2.0241   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    0.9451   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -1.1185   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -2.3087   -1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -4.6427   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -4.7366    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -5.9156   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332   -3.2670   -2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -3.6861   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -1.2568   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.2927    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866    1.6671    0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.1593   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5518    3.5413   -0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    4.1858   -0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    2.9407    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260    4.9987    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 15 16  1  0
  2  1  1  0
 13  7  1  0
  5 15  1  0
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 17 19  1  0
 19  3  1  0
  3  4  1  0
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 13 12  1  0
  8  9  2  0
  9 10  1  0
 10 12  1  0
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 19 20  1  0
 13 14  1  0
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  5 25  1  6
 19 39  1  1
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  2 22  1  0
  2 23  1  0
  3 24  1  6
  1 21  1  0
 13 33  1  1
  7 26  1  6
  8 27  1  0
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 12 31  1  0
 12 32  1  0
 11 30  1  0
 14 34  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       2.716   0.459   1.684  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.923   1.609   1.990  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.934   1.867   0.849  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.143   0.673   0.685  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.746   0.765  -0.423  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.477  -0.459  -0.528  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.787  -1.493  -1.242  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.790  -2.595  -1.455  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.506  -3.895  -1.276  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.156  -4.395  -0.862  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.148  -5.519  -1.679  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.946  -3.345  -1.034  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.499  -1.984  -0.514  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.307  -2.078   0.904  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.766   1.891  -0.178  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.663   2.038  -1.288  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.022   3.209   0.036  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.944   4.249   0.396  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.030   3.071   1.141  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.788   4.277   1.220  0.00  0.00           O+0
HETATM   21  H   UNK     0       2.089  -0.282   1.566  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.596   2.458   2.137  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.400   1.404   2.930  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.514   2.024  -0.071  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.195   0.945  -1.356  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.520  -1.119  -2.239  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.789  -2.309  -1.772  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.280  -4.643  -1.428  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.211  -4.737   0.178  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.960  -5.916  -1.319  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.233  -3.267  -2.091  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.840  -3.686  -0.498  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.304  -1.257  -0.670  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.226  -1.293   1.147  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.387   1.667   0.699  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.076   1.159  -1.408  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.552   3.541  -0.898  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.672   4.186  -0.256  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.477   2.941   2.106  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.126   4.999   1.246  0.00  0.00           H+0
CONECT    1    2   21                                                       
CONECT    2    1    3   22   23                                             
CONECT    3   19    4    2   24                                             
CONECT    4    3    5                                                       
CONECT    5   15    4    6   25                                             
CONECT    6    7    5                                                       
CONECT    7   13    6    8   26                                             
CONECT    8    9    7   27                                                  
CONECT    9    8   10   28                                                  
CONECT   10    9   12   11   29                                             
CONECT   11   10   30                                                       
CONECT   12   13   10   31   32                                             
CONECT   13    7   12   14   33                                             
CONECT   14   13   34                                                       
CONECT   15   16    5   17   35                                             
CONECT   16   15   36                                                       
CONECT   17   18   15   19   37                                             
CONECT   18   17   38                                                       
CONECT   19   17    3   20   39                                             
CONECT   20   19   40                                                       
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
    2.7160    0.4587    1.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.6088    1.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9339    1.8666    0.8486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1434    0.6734    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.7645   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4586   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7871   -1.4934   -1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7898   -2.5953   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -3.8954   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -4.3948   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1480   -5.5194   -1.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -3.3451   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -1.9836   -0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3071   -2.0777    0.9039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    1.8908   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6630    2.0377   -1.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225    3.2086    0.0359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9443    4.2492    0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    3.0705    1.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7878    4.2772    1.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887   -0.2817    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965    2.4576    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003    1.4038    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    2.0241   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    0.9451   -1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -1.1185   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885   -2.3087   -1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -4.6427   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -4.7366    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -5.9156   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332   -3.2670   -2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -3.6861   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -1.2568   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.2927    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866    1.6671    0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.1593   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5518    3.5413   -0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    4.1858   -0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    2.9407    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260    4.9987    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 15 16  1  0
  2  1  1  0
 13  7  1  0
  5 15  1  0
 15 17  1  0
 17 19  1  0
 19  3  1  0
  3  4  1  0
  4  5  1  0
 13 12  1  0
  8  9  2  0
  9 10  1  0
 10 12  1  0
 10 11  1  0
  7  6  1  0
 19 20  1  0
 13 14  1  0
  7  8  1  0
  3  2  1  0
  5  6  1  0
  5 25  1  6
 19 39  1  1
 20 40  1  0
 17 37  1  6
 18 38  1  0
 15 35  1  1
 16 36  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  6
  1 21  1  0
 13 33  1  1
  7 26  1  6
  8 27  1  0
  9 28  1  0
 10 29  1  1
 12 31  1  0
 12 32  1  0
 11 30  1  0
 14 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₂₀O₈

Average Mass

292.2840 Da

Monoisotopic Mass

292.11582 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1R,4S,6S)-4,6-dihydroxycyclohex-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1R,4S,6S)-4,6-dihydroxycyclohex-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])C([H])=C([H])[C@@]([H])(O[H])C([H])([H])[C@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C12H20O8/c13-4-8-9(16)10(17)11(18)12(20-8)19-7-2-1-5(14)3-6(7)15/h1-2,5-18H,3-4H2/t5-,6+,7-,8-,9-,10+,11-,12-/m1/s1

InChI Key

FSZLXNSBZLJIOC-VIXLETMSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Itoa orientalis	JEOL database	Chai, X. Y., et al, J. Nat. Prod. 71, 814 (2008)

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
O-glycosyl compound
Oxane
Monosaccharide
Cyclitol or derivatives
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.8	ALOGPS
logP	-3.1	ChemAxon
logS	-0.08	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.48 m³·mol⁻¹	ChemAxon
Polarizability	28.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

24707775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24879104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chai, X. Y., et al. (2008). Chai, X. Y., et al, J. Nat. Prod. 71, 814 (2008) . J. Nat. Prod..

Showing NP-Card for itoside L (NP0033753)

MOL for NP0033753 (itoside L)

3D MOL for NP0033753 (itoside L)

3D SDF for NP0033753 (itoside L)

3D-SDF for NP0033753 (itoside L)

PDB for NP0033753 (itoside L)

3D PDB for NP0033753 (itoside L)

SMILES for NP0033753 (itoside L)

INCHI for NP0033753 (itoside L)

Structure for NP0033753 (itoside L)

3D Structure for NP0033753 (itoside L)