NP-MRD: Showing NP-Card for buddlejoside B (NP0032620)

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Record Information

Version

2.0

Created at

2021-06-19 23:22:39 UTC

Updated at

2021-06-30 00:01:55 UTC

NP-MRD ID

NP0032620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

buddlejoside B

Provided By

JEOL Database JEOL Logo

Description

Buddlejoside B 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. buddlejoside B is found in Buddleja crispa. buddlejoside B was first documented in 2007 (Jensen, S. R., et al.). Based on a literature review very few articles have been published on Buddlejoside B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101223D          

 60 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101223D          

 60 63  0  0  0  0            999 V2000
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    3.3587    0.2475    1.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.2704    2.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391    0.4823    3.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902    1.7496    3.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0801    2.5350    3.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332    2.2640    1.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9835    3.5122    1.5391 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198    1.5283    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -2.0160    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -3.1912   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -5.3527    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4134   -5.5020    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043   -7.2132    2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -4.6558    4.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5237   -5.0478    5.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699   -2.8776    5.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -2.3025    2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872    0.1176    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033    0.6620    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2652   -2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    0.5586   -2.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -1.8085   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    2.6503   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    1.1131   -0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147    2.7725    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828    3.6763    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627    1.5462    1.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159    3.0178    3.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227   -2.5698    3.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371   -1.2568    3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576    0.0661    4.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    2.0566    4.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6211    3.8347    2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2968    1.9528    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
  9  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5 26  1  0  0  0  0
 24 25  1  0  0  0  0
 26 55  1  1  0  0  0
 13 14  1  0  0  0  0
  7  8  1  0  0  0  0
  9 40  1  1  0  0  0
 18 19  1  0  0  0  0
  5  4  1  0  0  0  0
 15 24  1  0  0  0  0
  4  3  1  0  0  0  0
 24 22  1  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
 22 20  1  0  0  0  0
  2  1  2  0  0  0  0
 20 17  1  0  0  0  0
  9 10  1  0  0  0  0
 28 27  2  0  0  0  0
 26 13  1  0  0  0  0
 27 34  1  0  0  0  0
 13 12  1  0  0  0  0
 34 32  2  0  0  0  0
 12 11  1  0  0  0  0
 32 30  1  0  0  0  0
 11 10  2  0  0  0  0
 30 29  2  0  0  0  0
 29 28  1  0  0  0  0
 26  9  1  0  0  0  0
 30 31  1  0  0  0  0
 17 16  1  0  0  0  0
 32 33  1  0  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 15 44  1  1  0  0  0
 20 49  1  6  0  0  0
 21 50  1  0  0  0  0
 22 51  1  1  0  0  0
 23 52  1  0  0  0  0
 24 53  1  6  0  0  0
 25 54  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 17 45  1  1  0  0  0
 19 48  1  0  0  0  0
 13 43  1  6  0  0  0
 11 42  1  0  0  0  0
 10 41  1  0  0  0  0
  7 38  1  6  0  0  0
  6 37  1  0  0  0  0
  8 39  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
 28 56  1  0  0  0  0
 34 60  1  0  0  0  0
 29 57  1  0  0  0  0
 31 58  1  0  0  0  0
 33 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C(=O)OC([H])([H])C1=C([H])[C@@]([H])(O[H])[C@]2([H])C([H])=C([H])O[C@@]([H])(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O12/c23-7-15-17(27)18(28)19(29)22(33-15)34-21-16-10(6-13(25)11(16)3-4-31-21)8-32-20(30)9-1-2-12(24)14(26)5-9/h1-6,11,13,15-19,21-29H,7-8H2/t11-,13+,15+,16+,17-,18-,19+,21-,22-/m0/s1

> <INCHI_KEY>
LNWDBCZJPZTNQI-QGPCSWCTSA-N

> <FORMULA>
C22H26O12

> <MOLECULAR_WEIGHT>
482.438

> <EXACT_MASS>
482.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.11515119605858

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,4aR,5S,7aS)-5-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl 3,4-dihydroxybenzoate

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-1.2937006969999991

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.883321914993862

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.55746924474126

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615635954

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
112.96060000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4aR,5S,7aS)-5-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl 3,4-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    1.6909    0.0006   -0.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -0.5089    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -1.8012    1.2671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280   -2.6080    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017   -3.5141    1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -4.8033    1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -5.3707    2.6178 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2037   -6.6240    2.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019   -4.3340    3.7277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2556   -4.1876    4.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -3.0288    4.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -1.8775    4.1547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8923   -2.0076    2.9422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3030   -0.7396    2.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    0.1501    1.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3270   -0.2899    0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.5911   -0.2080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1861   -0.0639   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568   -1.3210   -1.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    1.9679   -0.2758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1235    1.9191   -0.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    2.5396    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5907    3.7784    1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089    1.5711    2.0828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7156    2.0889    3.4204 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -3.0215    3.0104 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3587    0.2475    1.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.2704    2.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391    0.4823    3.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902    1.7496    3.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0801    2.5350    3.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332    2.2640    1.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9835    3.5122    1.5391 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198    1.5283    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -2.0160    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -3.1912   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -5.3527    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4134   -5.5020    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043   -7.2132    2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -4.6558    4.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5237   -5.0478    5.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699   -2.8776    5.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -2.3025    2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872    0.1176    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033    0.6620    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2652   -2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    0.5586   -2.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -1.8085   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    2.6503   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    1.1131   -0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147    2.7725    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828    3.6763    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627    1.5462    1.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159    3.0178    3.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227   -2.5698    3.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371   -1.2568    3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576    0.0661    4.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    2.0566    4.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6211    3.8347    2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2968    1.9528    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 20 21  1  0
 22 23  1  0
  9  7  1  0
  7  6  1  0
  6  5  2  0
  5 26  1  0
 24 25  1  0
 26 55  1  1
 13 14  1  0
  7  8  1  0
  9 40  1  1
 18 19  1  0
  5  4  1  0
 15 24  1  0
  4  3  1  0
 24 22  1  0
  3  2  1  0
  2 27  1  0
 22 20  1  0
  2  1  2  0
 20 17  1  0
  9 10  1  0
 28 27  2  0
 26 13  1  0
 27 34  1  0
 13 12  1  0
 34 32  2  0
 12 11  1  0
 32 30  1  0
 11 10  2  0
 30 29  2  0
 29 28  1  0
 26  9  1  0
 30 31  1  0
 17 16  1  0
 32 33  1  0
 17 18  1  0
 15 14  1  0
 15 44  1  1
 20 49  1  6
 21 50  1  0
 22 51  1  1
 23 52  1  0
 24 53  1  6
 25 54  1  0
 18 46  1  0
 18 47  1  0
 17 45  1  1
 19 48  1  0
 13 43  1  6
 11 42  1  0
 10 41  1  0
  7 38  1  6
  6 37  1  0
  8 39  1  0
  4 35  1  0
  4 36  1  0
 28 56  1  0
 34 60  1  0
 29 57  1  0
 31 58  1  0
 33 59  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       1.691   0.001  -0.025  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.360  -0.509   0.863  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.317  -1.801   1.267  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.328  -2.608   0.626  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.702  -3.514   1.639  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.382  -4.803   1.451  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.351  -5.371   2.618  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.204  -6.624   2.975  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.102  -4.334   3.728  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.256  -4.188   4.669  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.895  -3.029   4.837  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.644  -1.878   4.155  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.892  -2.008   2.942  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.303  -0.740   2.634  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.208   0.150   1.982  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.327  -0.290   0.626  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.095   0.591  -0.208  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.186  -0.064  -1.589  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.857  -1.321  -1.469  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.433   1.968  -0.276  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.124   1.919  -0.861  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.318   2.540   1.136  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.591   3.778   1.112  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.609   1.571   2.083  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.716   2.089   3.420  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.267  -3.022   3.010  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.359   0.248   1.664  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.919  -0.270   2.845  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.839   0.482   3.584  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.190   1.750   3.137  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.080   2.535   3.814  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.633   2.264   1.968  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.984   3.512   1.539  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.720   1.528   1.227  0.00  0.00           C+0
HETATM   35  H   UNK     0       0.541  -2.016   0.151  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.829  -3.191  -0.154  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.561  -5.353   0.537  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.413  -5.502   2.384  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.104  -7.213   2.209  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.761  -4.656   4.330  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.524  -5.048   5.277  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.670  -2.878   5.579  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.593  -2.303   2.148  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.187   0.118   2.477  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.103   0.662   0.221  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.195  -0.265  -2.009  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.751   0.559  -2.289  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.369  -1.809  -0.779  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.020   2.650  -0.901  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.350   1.113  -0.546  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.315   2.773   1.531  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.083   3.676   0.406  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.463   1.546   1.859  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.416   3.018   3.362  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.123  -2.570   3.531  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.637  -1.257   3.207  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.258   0.066   4.495  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.363   2.057   4.613  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.621   3.835   2.207  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.297   1.953   0.320  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   27    1                                                  
CONECT    3    4    2                                                       
CONECT    4    5    3   35   36                                             
CONECT    5    6   26    4                                                  
CONECT    6    7    5   37                                                  
CONECT    7    9    6    8   38                                             
CONECT    8    7   39                                                       
CONECT    9    7   40   10   26                                             
CONECT   10    9   11   41                                                  
CONECT   11   12   10   42                                                  
CONECT   12   13   11                                                       
CONECT   13   14   26   12   43                                             
CONECT   14   13   15                                                       
CONECT   15   16   24   14   44                                             
CONECT   16   15   17                                                       
CONECT   17   20   16   18   45                                             
CONECT   18   19   17   46   47                                             
CONECT   19   18   48                                                       
CONECT   20   21   22   17   49                                             
CONECT   21   20   50                                                       
CONECT   22   23   24   20   51                                             
CONECT   23   22   52                                                       
CONECT   24   25   15   22   53                                             
CONECT   25   24   54                                                       
CONECT   26    5   55   13    9                                             
CONECT   27    2   28   34                                                  
CONECT   28   27   29   56                                                  
CONECT   29   30   28   57                                                  
CONECT   30   32   29   31                                                  
CONECT   31   30   58                                                       
CONECT   32   34   30   33                                                  
CONECT   33   32   59                                                       
CONECT   34   27   32   60                                                  
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   15                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   31                                                            
CONECT   59   33                                                            
CONECT   60   34                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
    1.6909    0.0006   -0.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -0.5089    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -1.8012    1.2671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280   -2.6080    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017   -3.5141    1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -4.8033    1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -5.3707    2.6178 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2037   -6.6240    2.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019   -4.3340    3.7277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2556   -4.1876    4.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -3.0288    4.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -1.8775    4.1547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8923   -2.0076    2.9422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3030   -0.7396    2.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    0.1501    1.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3270   -0.2899    0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.5911   -0.2080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1861   -0.0639   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568   -1.3210   -1.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    1.9679   -0.2758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1235    1.9191   -0.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    2.5396    1.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5907    3.7784    1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089    1.5711    2.0828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7156    2.0889    3.4204 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -3.0215    3.0104 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3587    0.2475    1.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.2704    2.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391    0.4823    3.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902    1.7496    3.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0801    2.5350    3.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332    2.2640    1.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9835    3.5122    1.5391 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198    1.5283    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -2.0160    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -3.1912   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -5.3527    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4134   -5.5020    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043   -7.2132    2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -4.6558    4.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5237   -5.0478    5.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699   -2.8776    5.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -2.3025    2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872    0.1176    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033    0.6620    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2652   -2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    0.5586   -2.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -1.8085   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    2.6503   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    1.1131   -0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147    2.7725    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828    3.6763    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627    1.5462    1.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159    3.0178    3.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227   -2.5698    3.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371   -1.2568    3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576    0.0661    4.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    2.0566    4.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6211    3.8347    2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2968    1.9528    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 20 21  1  0
 22 23  1  0
  9  7  1  0
  7  6  1  0
  6  5  2  0
  5 26  1  0
 24 25  1  0
 26 55  1  1
 13 14  1  0
  7  8  1  0
  9 40  1  1
 18 19  1  0
  5  4  1  0
 15 24  1  0
  4  3  1  0
 24 22  1  0
  3  2  1  0
  2 27  1  0
 22 20  1  0
  2  1  2  0
 20 17  1  0
  9 10  1  0
 28 27  2  0
 26 13  1  0
 27 34  1  0
 13 12  1  0
 34 32  2  0
 12 11  1  0
 32 30  1  0
 11 10  2  0
 30 29  2  0
 29 28  1  0
 26  9  1  0
 30 31  1  0
 17 16  1  0
 32 33  1  0
 17 18  1  0
 15 14  1  0
 15 44  1  1
 20 49  1  6
 21 50  1  0
 22 51  1  1
 23 52  1  0
 24 53  1  6
 25 54  1  0
 18 46  1  0
 18 47  1  0
 17 45  1  1
 19 48  1  0
 13 43  1  6
 11 42  1  0
 10 41  1  0
  7 38  1  6
  6 37  1  0
  8 39  1  0
  4 35  1  0
  4 36  1  0
 28 56  1  0
 34 60  1  0
 29 57  1  0
 31 58  1  0
 33 59  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₁₂

Average Mass

482.4380 Da

Monoisotopic Mass

482.14243 Da

IUPAC Name

[(1S,4aR,5S,7aS)-5-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl 3,4-dihydroxybenzoate

Traditional Name

[(1S,4aR,5S,7aS)-5-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl 3,4-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C(=O)OC([H])([H])C1=C([H])[C@@]([H])(O[H])[C@]2([H])C([H])=C([H])O[C@@]([H])(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])[C@]12[H]

InChI Identifier

InChI=1S/C22H26O12/c23-7-15-17(27)18(28)19(29)22(33-15)34-21-16-10(6-13(25)11(16)3-4-31-21)8-32-20(30)9-1-2-12(24)14(26)5-9/h1-6,11,13,15-19,21-29H,7-8H2/t11-,13+,15+,16+,17-,18-,19+,21-,22-/m0/s1

InChI Key

LNWDBCZJPZTNQI-QGPCSWCTSA-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
Buddleja crispa	JEOL database	Jensen, S. R., et al, J. Nat. Prod. 70, 29 (2007)

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
P-hydroxybenzoic acid alkyl ester
Dihydroxybenzoic acid
Iridoid-skeleton
O-glycosyl compound
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Bicyclic monoterpenoid
Aromatic monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.77	ALOGPS
logP	-1.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.96 m³·mol⁻¹	ChemAxon
Polarizability	46.12 Å³	ChemAxon
Number of Rings	4	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24829301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jensen, S. R., et al. (2007). Jensen, S. R., et al, J. Nat. Prod. 70, 29 (2007) . J. Nat. Prod..

Showing NP-Card for buddlejoside B (NP0032620)

MOL for NP0032620 (buddlejoside B)

3D MOL for NP0032620 (buddlejoside B)

3D SDF for NP0032620 (buddlejoside B)

3D-SDF for NP0032620 (buddlejoside B)

PDB for NP0032620 (buddlejoside B)

3D PDB for NP0032620 (buddlejoside B)

SMILES for NP0032620 (buddlejoside B)

INCHI for NP0032620 (buddlejoside B)

Structure for NP0032620 (buddlejoside B)

3D Structure for NP0032620 (buddlejoside B)