NP-MRD: Showing NP-Card for Daphylloside (NP0139711)

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Record Information

Version

2.0

Created at

2022-06-29 20:07:03 UTC

Updated at

2022-06-29 20:07:04 UTC

NP-MRD ID

NP0139711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Daphylloside

Description

Daphylloside 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. Daphylloside is found in Cruciata laevipes, Daphniphyllum angustifolium, Daphniphyllum macropodum, Escallonia myrtoidea, Galium album, Galium humifusum, Galium mirum, Galium mollugo, Globularia bisnagarica, Oldenlandia hedyotidea, Lamium amplexicaule, Oldenlandia herbacea, Paederia scandens, Catunaregam spinosa and Spermacoce latifolia. Daphylloside was first documented in 2004 (PMID: 15214489). Based on a literature review a small amount of articles have been published on Daphylloside (PMID: 30080008) (PMID: 32647482) (PMID: 25095345) (PMID: 24427927).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222072D          

 31 33  0  0  1  0            999 V2000
    0.4507    2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083    2.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4990    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  6  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 19  1  6  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 22 29  1  1  0  0  0
 21 30  1  6  0  0  0
  8 31  1  1  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    2.2257    5.6303   -3.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6647    4.3623   -3.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    3.5085   -2.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3555    3.9086   -2.2575 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7081    2.2148   -2.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.8734   -3.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521    0.6270   -2.8651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2817    0.1298   -1.5335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4635   -1.0171   -1.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -0.9404   -0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4290   -1.9139    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635   -1.7408    1.4366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5404   -3.0232    2.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4935   -2.8262    3.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7370   -1.4050    0.8968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9029   -0.0017    0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7784   -1.8934   -0.5355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4605   -3.2509   -0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7903   -1.0566   -1.3232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3545    0.2042   -1.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593   -0.0274   -1.4082 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2061   -0.4090   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -1.8539    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -2.0556    1.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -1.5974    2.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -1.8510    4.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0089   -0.9145    2.7398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5350    0.6627    0.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3659    1.9243   -0.1940 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2085    2.5956    0.0941 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    1.3271   -1.5899 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3965    6.3467   -4.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9245    5.8987   -3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680    5.5972   -4.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929    2.5580   -3.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1052    0.8960   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456    0.0918   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0525   -0.9586    2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5853   -3.2769    2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -3.8575    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696   -1.8556    3.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5491   -1.8624    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7270    0.2382    0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8090   -1.7757   -0.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585   -3.3935   -1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005   -1.5515   -2.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6886    0.3191   -2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364   -0.7272   -2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2593   -2.3340    0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725   -2.3907   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619   -2.8721    4.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2420   -1.0632    4.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016   -1.8713    4.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9053    0.6691    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    2.5080   -0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302    2.3232    1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4331    1.1536   -1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 31  1  0
 31 29  1  0
 29 30  1  0
 29 28  1  0
 28 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 31  5  1  0
 19 10  1  0
 22 21  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  8 36  1  1
 10 37  1  1
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  1
 16 43  1  0
 17 44  1  6
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  6
 31 57  1  6
 29 55  1  6
 30 56  1  0
 28 54  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END


  Mrv1652306292222072D          

 31 33  0  0  1  0            999 V2000
    0.4507    2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083    2.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4990    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  6  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 19  1  6  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 22 29  1  1  0  0  0
 21 30  1  6  0  0  0
  8 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0139711

> <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]1[C@@H](O)C=C2COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O12/c1-7(21)28-5-8-3-10(22)13-9(17(26)27-2)6-29-18(12(8)13)31-19-16(25)15(24)14(23)11(4-20)30-19/h3,6,10-16,18-20,22-25H,4-5H2,1-2H3/t10-,11+,12+,13-,14+,15-,16+,18-,19-/m0/s1

> <INCHI_KEY>
YSOBQIMODQOGKQ-HOZAMIDDSA-N

> <FORMULA>
C19H26O12

> <MOLECULAR_WEIGHT>
446.405

> <EXACT_MASS>
446.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.701829815464556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-2.9264632319999997

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.176977893186454

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204478199184548

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615636256

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
99.09659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       0.841   5.161   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.189   4.017   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.696   4.337   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.287   2.552   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.864  -0.533   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.197  -5.153   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.864  -5.153   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.864  -6.693   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.864   2.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864   4.087   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.198   4.857   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.531   4.087   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.531   2.547   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.198   1.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.865   1.777   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.865   0.237   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.865   4.857   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.198   6.397   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.530   4.857   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.744  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   11   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   22                                                            
CONECT   30   21                                                            
CONECT   31    8                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₁₂

Average Mass

446.4050 Da

Monoisotopic Mass

446.14243 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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]1[C@@H](O)C=C2COC(C)=O

InChI Identifier

InChI=1S/C19H26O12/c1-7(21)28-5-8-3-10(22)13-9(17(26)27-2)6-29-18(12(8)13)31-19-16(25)15(24)14(23)11(4-20)30-19/h3,6,10-16,18-20,22-25H,4-5H2,1-2H3/t10-,11+,12+,13-,14+,15-,16+,18-,19-/m0/s1

InChI Key

YSOBQIMODQOGKQ-HOZAMIDDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Cruciata laevipes	LOTUS Database	35616633
Daphniphyllum angustifolium	LOTUS Database	35616633
Daphniphyllum macropodum	LOTUS Database	35616633
Escallonia myrtoidea	LOTUS Database	35616633
Galium album	LOTUS Database	35616633
Galium humifusum	LOTUS Database	35616633
Galium mirum	LOTUS Database	35616633
Galium mollugo	LOTUS Database	35616633
Globularia bisnagarica	LOTUS Database	35616633
Hedyotis hedyotidea	LOTUS Database	35616633
Lamium amplexicaule	LOTUS Database	35616633
Oldenlandia herbacea	LOTUS Database	35616633
Paederia scandens	LOTUS Database	35616633
Randia dumetorum	LOTUS Database	35616633
Spermacoce latifolia	LOTUS Database	35616633

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
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031721

Chemspider ID

10232877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21602024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma H, Li FL, Wang F, Guo Q, Cao GS, Yang PM: [Chemical Constituents from Oldenlandia diffusa]. Zhong Yao Cai. 2016 Jan;39(1):98-102. [PubMed:30080008 ]
Calis I, Weas A, Soliman Yusufoglu H, Donmez AA, Jensen SR: Iridoid glucosides from Wendlandia ligustroides (Boiss. &Hohen.) Blakelock. Saudi Pharm J. 2020 Jul;28(7):814-818. doi: 10.1016/j.jsps.2020.05.009. Epub 2020 Jun 3. [PubMed:32647482 ]
Zuo YM, Zhang ZL, Wang YY, Chen LY, Liu RH, Li YY: [Study on chemical constituents of iridoids from eucommiae folium]. Zhong Yao Cai. 2014 Feb;37(2):252-4. [PubMed:25095345 ]
Van Long LH, Nga VT, Dam NP, Hung MA, Dung TD, Quang TT, Phung NK: Three new iridoid glucoside salts from Hedyotis tenelliflora Growing in Vietnam. Nat Prod Commun. 2013 Nov;8(11):1507-8. [PubMed:24427927 ]
Raju BL, Lin SJ, Hou WC, Lai ZY, Liu PC, Hsu FL: Antioxidant iridoid glucosides from Wendlandia formosana. Nat Prod Res. 2004 Aug;18(4):357-64. doi: 10.1080/14786410310001622013. [PubMed:15214489 ]

Showing NP-Card for Daphylloside (NP0139711)

MOL for NP0139711 (Daphylloside)

3D MOL for NP0139711 (Daphylloside)

3D SDF for NP0139711 (Daphylloside)

3D-SDF for NP0139711 (Daphylloside)

PDB for NP0139711 (Daphylloside)

3D PDB for NP0139711 (Daphylloside)

SMILES for NP0139711 (Daphylloside)

INCHI for NP0139711 (Daphylloside)

Structure for NP0139711 (Daphylloside)

3D Structure for NP0139711 (Daphylloside)