NP-MRD: Showing NP-Card for Gardoside methyl ester (NP0074713)

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Record Information

Version

2.0

Created at

2022-04-28 20:01:22 UTC

Updated at

2022-04-28 20:01:22 UTC

NP-MRD ID

NP0074713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gardoside methyl ester

Description

Gardoside methyl ester 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. Gardoside methyl ester is found in Aragoa cundinamarcensis, Castilleja attenuata, Castilleja miniata, Castilleja occidentalis, Mackaya bella, Melampyrum cristatum, Pedicularis artselaeri, Pedicularis palustris, Pedicularis spicata, Pedicularis torta, Penstemon acuminatus, Penstemon auriberbis and Rhinanthus angustifolius. Gardoside methyl ester was first documented in 2003 (PMID: 12943770). Based on a literature review a small amount of articles have been published on Gardoside methyl ester (PMID: 23298403) (PMID: 34526896) (PMID: 18491284).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222012D          

 27 29  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  1  0  0  0
 21 23  1  6  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -1.6113   -1.0775    3.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -1.2748    1.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5510   -2.4295    1.2687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6837   -2.8122    2.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099   -1.9285   -0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841   -0.4385   -0.0603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6194    0.1791   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6243    1.0651   -1.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6514    1.3181   -1.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5102    1.6715   -3.1294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4910    2.5358   -3.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -0.1311   -2.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466   -1.0053   -1.3913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -0.8508   -0.0121 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8219   -0.1833    0.0631 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -0.7480    0.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4092   -0.0559    1.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9653    1.1684    1.3529 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0434    2.1932    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8229    3.3631    0.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2175    1.1193    0.4999 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3532    1.5224    1.1896 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -0.3026   -0.0037 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3090   -0.4026   -1.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -0.6630   -0.6093 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0865   -1.8725   -1.3090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984   -0.3630    0.7708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0968   -0.2012    3.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.7986    3.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218   -3.3300    1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9534   -3.7301    1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -2.4000   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0911   -2.0974   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804    0.0771    0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1215    2.9197   -4.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4851    2.0533   -3.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870    3.4172   -2.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    0.2888   -3.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1272   -1.9072    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207   -1.8098    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2896    1.5778    2.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.9503   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196    2.4905    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    3.6248    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1069    1.7561   -0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1483    1.4564    2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373   -0.9710    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8502   -1.2084   -0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7725    0.1117   -1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849   -2.5614   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4350    0.6943    1.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 27  1  0
 27  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  6  7  1  0
 25 16  1  0
  2 27  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  1
 16 40  1  1
 18 41  1  1
 19 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  6
 22 46  1  0
 23 47  1  1
 24 48  1  0
 25 49  1  6
 26 50  1  0
 27 51  1  1
  6 34  1  1
  5 32  1  0
  5 33  1  0
  3 30  1  6
  4 31  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652304282222012D          

 27 29  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  1  0  0  0
 21 23  1  6  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1C[C@H](O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5,7,9-14,16-22H,1,3-4H2,2H3/t7-,9+,10-,11-,12-,13+,14-,16+,17+/m1/s1

> <INCHI_KEY>
AFFNBNJOIDYUQN-QUQWIGIVSA-N

> <FORMULA>
C17H24O10

> <MOLECULAR_WEIGHT>
388.369

> <EXACT_MASS>
388.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.72569443384606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.62

> <JCHEM_LOGP>
-2.106837545333333

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.183407265880483

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205243529081958

> <JCHEM_PKA_STRONGEST_BASIC>
-2.975798160452947

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
87.17489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.46e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       6.258   3.613   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.259   9.003   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.925  11.313   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.590  -1.007   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.258  -1.007   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17                                                            
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21    4                                                       
CONECT   23   21                                                            
CONECT   24    3   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₁₀

Average Mass

388.3690 Da

Monoisotopic Mass

388.13695 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1C[C@H](O)C2=C

InChI Identifier

InChI=1S/C17H24O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5,7,9-14,16-22H,1,3-4H2,2H3/t7-,9+,10-,11-,12-,13+,14-,16+,17+/m1/s1

InChI Key

AFFNBNJOIDYUQN-QUQWIGIVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aragoa cundinamarcensis	Plant	KNApSAcK
Castilleja attenuata	LOTUS Database	35616633
Castilleja miniata	LOTUS Database	35616633
Castilleja occidentalis	LOTUS Database	35616633
Mackaya bella	LOTUS Database	35616633
Melampyrum cristatum	LOTUS Database	35616633
Pedicularis artselaeri	LOTUS Database	35616633
Pedicularis palustris	LOTUS Database	35616633
Pedicularis spicata	LOTUS Database	35616633
Pedicularis torta	LOTUS Database	35616633
Penstemon acuminatus	LOTUS Database	35616633
Penstemon auriberbis	LOTUS Database	35616633
Rhinanthus angustifolius	LOTUS Database	35616633

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
Monosaccharide
Oxane
Cyclic alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
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	-1.6	ALOGPS
logP	-2.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.17 m³·mol⁻¹	ChemAxon
Polarizability	37.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036118

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

51692952

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Venditti A, Serrilli AM, Bianco A: Iridoids from Bellardia trixago (L.) All. Nat Prod Res. 2013 Aug;27(15):1413-6. doi: 10.1080/14786419.2012.746342. Epub 2013 Jan 9. [PubMed:23298403 ]
Ji M, Wang C, Yang T, Meng X, Wang X, Li M: Integrated Phytochemical Analysis Based on UPLC-MS/MS and Network Pharmacology Approaches to Explore the Effect of Odontites vulgaris Moench on Rheumatoid Arthritis. Front Pharmacol. 2021 Aug 30;12:707687. doi: 10.3389/fphar.2021.707687. eCollection 2021. [PubMed:34526896 ]
Li CM, Zhang XL, Xue XY, Zhang FF, Xu Q, Liang XM: Structural characterization of iridoid glucosides by ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008 Jun;22(12):1941-54. doi: 10.1002/rcm.3579. [PubMed:18491284 ]
Ronsted N, Bello MA, Jensen SR: Aragoside and iridoid glucosides from Aragoa cundinamarcensis. Phytochemistry. 2003 Sep;64(2):529-33. doi: 10.1016/s0031-9422(03)00157-2. [PubMed:12943770 ]

Showing NP-Card for Gardoside methyl ester (NP0074713)

MOL for NP0074713 (Gardoside methyl ester)

3D MOL for NP0074713 (Gardoside methyl ester)

3D SDF for NP0074713 (Gardoside methyl ester)

3D-SDF for NP0074713 (Gardoside methyl ester)

PDB for NP0074713 (Gardoside methyl ester)

3D PDB for NP0074713 (Gardoside methyl ester)

SMILES for NP0074713 (Gardoside methyl ester)

INCHI for NP0074713 (Gardoside methyl ester)

Structure for NP0074713 (Gardoside methyl ester)

3D Structure for NP0074713 (Gardoside methyl ester)