NP-MRD: Showing NP-Card for ajureptaside A (NP0040690)

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Record Information

Version

2.0

Created at

2021-06-20 22:47:05 UTC

Updated at

2021-06-30 00:14:44 UTC

NP-MRD ID

NP0040690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajureptaside A

Provided By

JEOL Database JEOL Logo

Description

(1S)-1alpha-(beta-D-Glucopyranosyloxy)-3beta-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4alpha,4aalpha,5alpha,7alpha-tetraol 7-acetate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. ajureptaside A is found in Ajuga reptans. ajureptaside A was first documented in 2011 (Ono, M., et al.). Based on a literature review very few articles have been published on (1S)-1alpha-(beta-D-Glucopyranosyloxy)-3beta-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4alpha,4aalpha,5alpha,7alpha-tetraol 7-acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100473D          

 61 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212100473D          

 61 63  0  0  0  0            999 V2000
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    2.1322   -1.7749    1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591   -2.1466    2.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8289   -3.5819    2.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.4217    2.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908   -0.4223    0.9639 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9704    0.6888   -0.0650 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1493    0.5566   -0.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081    0.4547   -0.9051 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9915   -0.6566   -1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    1.6600   -1.7612 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3290    1.1814   -2.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1857    5.5968    0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576    4.7544    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236    5.4332   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    3.3296   -1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    0.9703    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    0.0460    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2275   -2.2504    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827   -4.2988   -1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -3.4058   -2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172   -3.0036   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256   -1.7677   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5263   -2.8480   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2276   -0.4503   -0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505   -0.7826   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    0.8546   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784    2.0488   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -0.9147   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    1.5401    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    0.1433    3.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2531    0.5278    3.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103   -3.9119    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -4.2047    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3183   -3.6884    3.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -1.3904    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5924   -0.2587    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827    1.6641    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9622   -0.1739   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -0.5063   -2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    2.0073   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1617   -2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  6  1  0  0  0  0
 28 26  1  0  0  0  0
 26 25  1  0  0  0  0
 25 19  1  0  0  0  0
 19 18  1  0  0  0  0
  3 30  1  0  0  0  0
  3  2  1  0  0  0  0
 18 28  1  0  0  0  0
 19 20  1  0  0  0  0
 30 31  1  0  0  0  0
  7 16  1  0  0  0  0
 16 14  1  0  0  0  0
 14 12  1  0  0  0  0
 12  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 28 30  1  0  0  0  0
 10 11  1  0  0  0  0
 28 29  1  6  0  0  0
 21 22  1  0  0  0  0
 18  5  1  0  0  0  0
 22 23  1  0  0  0  0
 26 27  1  0  0  0  0
 22 24  2  0  0  0  0
  5  4  1  0  0  0  0
  2  1  1  0  0  0  0
 19 21  1  1  0  0  0
 18 48  1  6  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
  5 36  1  1  0  0  0
  3 35  1  6  0  0  0
 30 60  1  6  0  0  0
 26 57  1  1  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
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 31 61  1  0  0  0  0
 29 59  1  0  0  0  0
 27 58  1  0  0  0  0
  7 37  1  1  0  0  0
 12 42  1  6  0  0  0
 13 43  1  0  0  0  0
 14 44  1  1  0  0  0
 15 45  1  0  0  0  0
 16 46  1  6  0  0  0
 17 47  1  0  0  0  0
 10 39  1  0  0  0  0
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  9 38  1  1  0  0  0
 11 41  1  0  0  0  0
 23 52  1  0  0  0  0
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 23 54  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])O[C@@]([H])(OC([H])([H])[H])[C@]([H])(O[H])[C@@]3(O[H])[C@]([H])(O[H])C([H])([H])[C@@](OC(=O)C([H])([H])[H])(C([H])([H])[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O13/c1-6(20)31-17(2)4-8(21)18(26)12(17)15(30-16(27-3)13(18)25)29-14-11(24)10(23)9(22)7(5-19)28-14/h7-16,19,21-26H,4-5H2,1-3H3/t7-,8-,9-,10+,11-,12-,13+,14+,15-,16-,17+,18-/m1/s1

> <INCHI_KEY>
MXRGTGBSDPJUGH-DDORWGBXSA-N

> <FORMULA>
C18H30O13

> <MOLECULAR_WEIGHT>
454.425

> <EXACT_MASS>
454.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.53170691786173

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4R,4aS,5R,7S,7aS)-4,4a,5-trihydroxy-3-methoxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydrocyclopenta[c]pyran-7-yl acetate

> <ALOGPS_LOGP>
-1.78

> <JCHEM_LOGP>
-4.549604510000002

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.345522040795458

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.766175117200758

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084758765247

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
95.25089999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,4aS,5R,7S,7aS)-4,4a,5-trihydroxy-3-methoxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydrocyclopenta[c]pyran-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    2.3277    4.9363   -0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    3.7231   -0.6175 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1871    2.3558    0.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    1.0787    0.2963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4218    1.0769   -0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814    0.1372   -0.5200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0897   -1.1212   -1.0721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0710   -2.1463   -0.8493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4937   -3.4660   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2740   -3.7561   -0.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.7882   -1.5628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4172   -2.7423   -1.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8606   -0.4057   -1.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9877    0.0097   -1.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2234    1.8691   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.0105    0.1042 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4153   -0.4069    1.4050 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2738    0.5117    2.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322   -1.7749    1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591   -2.1466    2.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8289   -3.5819    2.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.4217    2.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908   -0.4223    0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704    0.6888   -0.0650 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1493    0.5566   -0.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081    0.4547   -0.9051 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9915   -0.6566   -1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    1.6600   -1.7612 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3290    1.1814   -2.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1857    5.5968    0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576    4.7544    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236    5.4332   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    3.3296   -1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    0.9703    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    0.0460    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2275   -2.2504    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827   -4.2988   -1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -3.4058   -2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172   -3.0036   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256   -1.7677   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5263   -2.8480   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2276   -0.4503   -0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505   -0.7826   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    0.8546   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784    2.0488   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -0.9147   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    1.5401    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    0.1433    3.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2531    0.5278    3.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103   -3.9119    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -4.2047    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3183   -3.6884    3.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -1.3904    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5924   -0.2587    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827    1.6641    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9622   -0.1739   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -0.5063   -2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    2.0073   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1617   -2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  5  6  1  0
 28 26  1  0
 26 25  1  0
 25 19  1  0
 19 18  1  0
  3 30  1  0
  3  2  1  0
 18 28  1  0
 19 20  1  0
 30 31  1  0
  7 16  1  0
 16 14  1  0
 14 12  1  0
 12  9  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 14 15  1  0
 16 17  1  0
 28 30  1  0
 10 11  1  0
 28 29  1  6
 21 22  1  0
 18  5  1  0
 22 23  1  0
 26 27  1  0
 22 24  2  0
  5  4  1  0
  2  1  1  0
 19 21  1  1
 18 48  1  6
  9 10  1  0
  7  6  1  0
  5 36  1  1
  3 35  1  6
 30 60  1  6
 26 57  1  1
 25 55  1  0
 25 56  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 31 61  1  0
 29 59  1  0
 27 58  1  0
  7 37  1  1
 12 42  1  6
 13 43  1  0
 14 44  1  1
 15 45  1  0
 16 46  1  6
 17 47  1  0
 10 39  1  0
 10 40  1  0
  9 38  1  1
 11 41  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.328   4.936  -0.046  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.798   3.723  -0.618  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.734   2.807  -0.890  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.187   2.356   0.350  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.558   1.079   0.296  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.422   1.077  -0.748  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.481   0.137  -0.520  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.090  -1.121  -1.072  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.071  -2.146  -0.849  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.494  -3.466  -1.372  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.274  -3.756  -0.686  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.380  -1.788  -1.563  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.417  -2.742  -1.314  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.861  -0.406  -1.112  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.988   0.010  -1.899  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.753   0.643  -1.231  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.223   1.869  -0.652  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.627  -0.011   0.104  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.415  -0.407   1.405  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.274   0.512   2.629  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.132  -1.775   1.816  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.859  -2.147   2.112  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.829  -3.582   2.539  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.125  -1.422   2.053  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.891  -0.422   0.964  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.970   0.689  -0.065  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.149   0.557  -0.848  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.708   0.455  -0.905  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.991  -0.657  -1.801  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.302   1.660  -1.761  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.329   1.181  -2.726  0.00  0.00           O+0
HETATM   32  H   UNK     0       3.186   5.597   0.106  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.858   4.754   0.925  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.624   5.433  -0.720  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.947   3.330  -1.449  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.041   0.970   1.252  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.686   0.046   0.554  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.228  -2.250   0.232  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.183  -4.299  -1.204  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.263  -3.406  -2.440  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.317  -3.004  -0.881  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.226  -1.768  -2.649  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.526  -2.848  -0.351  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.228  -0.450  -0.079  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.551  -0.783  -2.011  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.538   0.855  -2.286  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.078   2.049  -1.092  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.159  -0.915  -0.294  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.578   1.540   2.414  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.896   0.143   3.453  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.253   0.528   3.021  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.210  -3.912   2.625  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.324  -4.205   1.790  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.318  -3.688   3.510  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.172  -1.390   0.528  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.592  -0.259   1.790  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.983   1.664   0.429  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.962  -0.174  -1.474  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.413  -0.506  -2.580  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.149   2.007  -2.364  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.460   1.162  -2.271  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1                                                       
CONECT    3    4   30    2   35                                             
CONECT    4    3    5                                                       
CONECT    5    6   18    4   36                                             
CONECT    6    5    7                                                       
CONECT    7   16    8    6   37                                             
CONECT    8    9    7                                                       
CONECT    9   12    8   10   38                                             
CONECT   10   11    9   39   40                                             
CONECT   11   10   41                                                       
CONECT   12   14    9   13   42                                             
CONECT   13   12   43                                                       
CONECT   14   16   12   15   44                                             
CONECT   15   14   45                                                       
CONECT   16    7   14   17   46                                             
CONECT   17   16   47                                                       
CONECT   18   19   28    5   48                                             
CONECT   19   25   18   20   21                                             
CONECT   20   19   49   50   51                                             
CONECT   21   22   19                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   52   53   54                                             
CONECT   24   22                                                            
CONECT   25   26   19   55   56                                             
CONECT   26   28   25   27   57                                             
CONECT   27   26   58                                                       
CONECT   28   26   18   30   29                                             
CONECT   29   28   59                                                       
CONECT   30    3   31   28   60                                             
CONECT   31   30   61                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

RDKit          3D

61 63  0  0  0  0  0  0  0  0999 V2000
    2.3277    4.9363   -0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    3.7231   -0.6175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337    2.8071   -0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1871    2.3558    0.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    1.0787    0.2963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4218    1.0769   -0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814    0.1372   -0.5200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0897   -1.1212   -1.0721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0710   -2.1463   -0.8493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4937   -3.4660   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2740   -3.7561   -0.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.7882   -1.5628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4172   -2.7423   -1.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8606   -0.4057   -1.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9877    0.0097   -1.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7528    0.6433   -1.2313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2234    1.8691   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.0105    0.1042 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4153   -0.4069    1.4050 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2738    0.5117    2.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322   -1.7749    1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591   -2.1466    2.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8289   -3.5819    2.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.4217    2.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908   -0.4223    0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704    0.6888   -0.0650 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1493    0.5566   -0.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081    0.4547   -0.9051 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9915   -0.6566   -1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    1.6600   -1.7612 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3290    1.1814   -2.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1857    5.5968    0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576    4.7544    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236    5.4332   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    3.3296   -1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    0.9703    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    0.0460    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2275   -2.2504    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827   -4.2988   -1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -3.4058   -2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172   -3.0036   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256   -1.7677   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5263   -2.8480   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2276   -0.4503   -0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505   -0.7826   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    0.8546   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784    2.0488   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -0.9147   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    1.5401    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    0.1433    3.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2531    0.5278    3.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103   -3.9119    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -4.2047    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3183   -3.6884    3.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -1.3904    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5924   -0.2587    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827    1.6641    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9622   -0.1739   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -0.5063   -2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    2.0073   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1617   -2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  5  6  1  0
 28 26  1  0
 26 25  1  0
 25 19  1  0
 19 18  1  0
  3 30  1  0
  3  2  1  0
 18 28  1  0
 19 20  1  0
 30 31  1  0
  7 16  1  0
 16 14  1  0
 14 12  1  0
 12  9  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 14 15  1  0
 16 17  1  0
 28 30  1  0
 10 11  1  0
 28 29  1  6
 21 22  1  0
 18  5  1  0
 22 23  1  0
 26 27  1  0
 22 24  2  0
  5  4  1  0
  2  1  1  0
 19 21  1  1
 18 48  1  6
  9 10  1  0
  7  6  1  0
  5 36  1  1
  3 35  1  6
 30 60  1  6
 26 57  1  1
 25 55  1  0
 25 56  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 31 61  1  0
 29 59  1  0
 27 58  1  0
  7 37  1  1
 12 42  1  6
 13 43  1  0
 14 44  1  1
 15 45  1  0
 16 46  1  6
 17 47  1  0
 10 39  1  0
 10 40  1  0
  9 38  1  1
 11 41  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S)-1a-(b-D-Glucopyranosyloxy)-3b-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4a,4aalpha,5a,7a-tetraol 7-acetate	Generator
(1S)-1a-(b-D-Glucopyranosyloxy)-3b-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4a,4aalpha,5a,7a-tetraol 7-acetic acid	Generator
(1S)-1alpha-(beta-D-Glucopyranosyloxy)-3beta-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4alpha,4aalpha,5alpha,7alpha-tetraol 7-acetic acid	Generator
(1S)-1Α-(β-D-glucopyranosyloxy)-3β-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4α,4aalpha,5α,7α-tetraol 7-acetate	Generator
(1S)-1Α-(β-D-glucopyranosyloxy)-3β-methoxy-7-methyl-1,3,4,4aalpha,5,6,7,7aalpha-octahydrocyclopenta[c]pyran-4α,4aalpha,5α,7α-tetraol 7-acetic acid	Generator

Chemical Formula

C₁₈H₃₀O₁₃

Average Mass

454.4250 Da

Monoisotopic Mass

454.16864 Da

IUPAC Name

(1S,3R,4R,4aS,5R,7S,7aS)-4,4a,5-trihydroxy-3-methoxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydrocyclopenta[c]pyran-7-yl acetate

Traditional Name

(1S,3R,4R,4aS,5R,7S,7aS)-4,4a,5-trihydroxy-3-methoxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydrocyclopenta[c]pyran-7-yl acetate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])O[C@@]([H])(OC([H])([H])[H])[C@]([H])(O[H])[C@@]3(O[H])[C@]([H])(O[H])C([H])([H])[C@@](OC(=O)C([H])([H])[H])(C([H])([H])[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C18H30O13/c1-6(20)31-17(2)4-8(21)18(26)12(17)15(30-16(27-3)13(18)25)29-14-11(24)10(23)9(22)7(5-19)28-14/h7-16,19,21-26H,4-5H2,1-3H3/t7-,8-,9-,10+,11-,12-,13+,14+,15-,16-,17+,18-/m1/s1

InChI Key

MXRGTGBSDPJUGH-DDORWGBXSA-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
Ajuga reptans	JEOL database	Ono, M., et al, Chem. Pharm. Bull. 59, 1065 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-4.5	ChemAxon
logS	-0.53	ALOGPS
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.25 m³·mol⁻¹	ChemAxon
Polarizability	42.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

28289039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53492928

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ono, M., et al. (2011). Ono, M., et al, Chem. Pharm. Bull. 59, 1065 (2011). Chem. Pharm. Bull..

Showing NP-Card for ajureptaside A (NP0040690)

MOL for NP0040690 (ajureptaside A)

3D MOL for NP0040690 (ajureptaside A)

3D SDF for NP0040690 (ajureptaside A)

3D-SDF for NP0040690 (ajureptaside A)

PDB for NP0040690 (ajureptaside A)

3D PDB for NP0040690 (ajureptaside A)

SMILES for NP0040690 (ajureptaside A)

INCHI for NP0040690 (ajureptaside A)

Structure for NP0040690 (ajureptaside A)

3D Structure for NP0040690 (ajureptaside A)