NP-MRD: Showing NP-Card for 8-O-Acetylharpagide (NP0139816)

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Record Information

Version

2.0

Created at

2022-06-29 20:12:04 UTC

Updated at

2022-06-29 20:12:04 UTC

NP-MRD ID

NP0139816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-O-Acetylharpagide

Description

8-O-Acetylharpagide 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. 8-O-Acetylharpagide is found in Ajuga decumbens, Ajuga pyramidalis, Ajuga reptans, Ajuga taiwanensis, Betonica macrantha, Leonurus turkestanicus, Otostegia fruticosa, Physostegia virginiana, Scrophularia deserti, Scrophularia hypericifolia, Stachys menthifolia and Vitex agnus-castus. 8-O-Acetylharpagide was first documented in 2018 (PMID: 29854582). Based on a literature review a small amount of articles have been published on 8-O-Acetylharpagide (PMID: 32279533) (PMID: 33673028) (PMID: 33184359) (PMID: 31018502).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222122D          

 28 30  0  0  1  0            999 V2000
   -2.2869    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    0.3820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  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  2  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    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
    2.7845    0.9521    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
    3.4990    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
    2.0701    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.8396    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
    4.2135    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9309    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
    0.1921    0.7232    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  5  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  2  0  0  0  0
  8 13  1  0  0  0  0
 10 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 18 23  1  1  0  0  0
 17 24  1  6  0  0  0
 16 25  1  1  0  0  0
  8 26  1  6  0  0  0
  7 27  1  6  0  0  0
  5 28  1  1  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -1.4508    2.9854    2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9863    1.8614    1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7434    2.1035    0.2884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944    0.5528    1.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356   -0.5738    0.7876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4983   -1.7550    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035   -0.7794    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942   -1.0081   -0.5783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7230    0.1372   -1.0624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596   -1.2357   -1.4263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0283   -0.6262   -2.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915   -2.6761   -1.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790   -3.1502   -1.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383   -2.2546   -1.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893   -1.1800   -0.9193 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4360   -0.2123   -1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    0.0443   -0.7241 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5451    1.3681   -0.2740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5283    1.4691    0.7067 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4124    2.7611    1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616    2.7248    2.4407 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896    1.3687    0.0718 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8426    1.4479    1.0959 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0171    0.0126   -0.5887 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1959    0.0067   -1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8403   -0.2590   -1.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8041   -1.5996   -1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -0.5945   -0.6524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7590    3.6230    1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    2.5612    2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3391    3.5453    2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -2.6476    0.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -1.9842    2.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -1.4872    1.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -1.6972    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1753    0.0390    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -1.8516   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8201   -0.0074   -2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -1.0087   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5407   -3.3355   -1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813   -4.2045   -2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387   -1.5329    0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697   -0.5880    0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.5940    1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    3.6096    0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    2.7902    2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2741    1.9438    3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457    2.1877   -0.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9840    0.5208    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -0.7450    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746   -0.1284   -2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624    0.4182   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599   -2.0389   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413    0.4851   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  4  1  1
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  2  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
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 28  1  0
 28  5  1  0
 28 10  1  0
 26 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  1
  9 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  1
 17 43  1  1
 19 44  1  1
 20 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  6
 23 49  1  0
 24 50  1  1
 25 51  1  0
 26 52  1  6
 27 53  1  0
 28 54  1  6
M  END


  Mrv1652306292222122D          

 28 30  0  0  1  0            999 V2000
   -2.2869    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    0.3820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  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  2  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    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
    2.7845    0.9521    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
    3.4990    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
    2.0701    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.8396    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
    4.2135    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9309    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
    0.1921    0.7232    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  5  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  2  0  0  0  0
  8 13  1  0  0  0  0
 10 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 18 23  1  1  0  0  0
 17 24  1  6  0  0  0
 16 25  1  1  0  0  0
  8 26  1  6  0  0  0
  7 27  1  6  0  0  0
  5 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0139816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@]1(C)C[C@@H](O)[C@]2(O)C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1

> <INCHI_KEY>
CAFTUQNGDROXEZ-XBDCZORHSA-N

> <FORMULA>
C17H26O11

> <MOLECULAR_WEIGHT>
406.384

> <EXACT_MASS>
406.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.785716470741825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-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-7-yl acetate

> <ALOGPS_LOGP>
-1.67

> <JCHEM_LOGP>
-3.790121225

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.780416162786157

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.119165313115994

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760235162

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
88.3554

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.65e+01 g/l

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

> <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      -4.269   0.713   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.935  -0.057   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.935  -1.597   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.602   0.713   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.864  -0.533   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.864   2.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.531   2.547   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.531   4.087   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.198   4.857   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.864   4.087   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.198   6.397   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.531   7.167   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.865   4.857   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.865   1.777   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.036  -3.604   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.744  -4.013   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.358   1.350   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   13   26                                             
CONECT    9    8    5   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   17                                                            
CONECT   25   16                                                            
CONECT   26    8                                                            
CONECT   27    7                                                            
CONECT   28    5                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
8-O-Acetylharpagid	MeSH

Chemical Formula

C₁₇H₂₆O₁₁

Average Mass

406.3840 Da

Monoisotopic Mass

406.14751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]1(C)C[C@@H](O)[C@]2(O)C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

InChI Identifier

InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1

InChI Key

CAFTUQNGDROXEZ-XBDCZORHSA-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
Ajuga decumbens	LOTUS Database	35616633
Ajuga pyramidalis	LOTUS Database	35616633
Ajuga reptans	LOTUS Database	35616633
Ajuga taiwanensis	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Leonurus turkestanicus	LOTUS Database	35616633
Otostegia fruticosa	LOTUS Database	35616633
Physostegia virginiana	LOTUS Database	35616633
Scrophularia deserti	LOTUS Database	35616633
Scrophularia hypericifolia	LOTUS Database	35616633
Stachys menthifolia	LOTUS Database	35616633
Vitex agnus-castus	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
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010570

Chemspider ID

8154242

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9978650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gokmen A, Kusz N, Karaca N, Demirci F, Hohmann J, Kirmizibekmez H: Secondary metabolites from Verbascum bugulifolium Lam. and their bioactivities. Nat Prod Res. 2021 Dec;35(23):5294-5298. doi: 10.1080/14786419.2020.1753052. Epub 2020 Apr 11. [PubMed:32279533 ]
Abdel-Kader MS, Alqasoumi SI: In Vivo Hepatoprotective and Nephroprotective Activity of Acylated Iridoid Glycosides from Scrophularia hepericifolia. Biology (Basel). 2021 Feb 12;10(2):145. doi: 10.3390/biology10020145. [PubMed:33673028 ]
Hsu WH, Lin BZ, Leu JD, Lo PH, Yu HY, Chen CT, Tu YH, Lin YL, Lee YJ: Involvement of 8-O-acetylharpagide for Ajuga taiwanensis mediated suppression of senescent phenotypes in human dermal fibroblasts. Sci Rep. 2020 Nov 12;10(1):19731. doi: 10.1038/s41598-020-76797-6. [PubMed:33184359 ]
Toiu A, Mocan A, Vlase L, Parvu AE, Vodnar DC, Gheldiu AM, Moldovan C, Oniga I: Comparative Phytochemical Profile, Antioxidant, Antimicrobial and In Vivo Anti-Inflammatory Activity of Different Extracts of Traditionally Used Romanian Ajuga genevensis L. and A. reptans L. (Lamiaceae). Molecules. 2019 Apr 23;24(8):1597. doi: 10.3390/molecules24081597. [PubMed:31018502 ]
Ganaie HA, Ali MN, Ganai BA, Bashir S: Antimutagenic activity of compounds isolated from Ajuga bracteosa Wall ex. Benth against EMS induced mutagenicity in mice. Toxicol Rep. 2017 Dec 22;5:108-112. doi: 10.1016/j.toxrep.2017.12.018. eCollection 2018. [PubMed:29854582 ]

Showing NP-Card for 8-O-Acetylharpagide (NP0139816)

MOL for NP0139816 (8-O-Acetylharpagide)

3D MOL for NP0139816 (8-O-Acetylharpagide)

3D SDF for NP0139816 (8-O-Acetylharpagide)

3D-SDF for NP0139816 (8-O-Acetylharpagide)

PDB for NP0139816 (8-O-Acetylharpagide)

3D PDB for NP0139816 (8-O-Acetylharpagide)

SMILES for NP0139816 (8-O-Acetylharpagide)

INCHI for NP0139816 (8-O-Acetylharpagide)

Structure for NP0139816 (8-O-Acetylharpagide)

3D Structure for NP0139816 (8-O-Acetylharpagide)