NP-MRD: Showing NP-Card for 2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0189456)

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Record Information

Version

2.0

Created at

2022-09-04 05:56:20 UTC

Updated at

2022-09-04 05:56:20 UTC

NP-MRD ID

NP0189456

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Harpagide, also known as myoporoside or ajugol, 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. 2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Ajuga decumbens, Ajuga nipponensis, Ajuga pyramidalis, Ajuga reptans, Ajuga taiwanensis, Angelonia integerrima, Betonica macrantha, Caryopteris incana, Caryopteris mongholica, Clerodendrum indicum, Harpagophytum procumbens, Harpagophytum zeyheri, Lagochilus platycalyx, Lamium galeobdolon, Penstemon serrulatus, Phlomoides tuberosa, Rogeria adenophylla, Scrophularia canina, Scrophularia ilwensis, Scrophularia leucoclada, Scrophularia ningpoensis, Scrophularia nodosa, Scrophularia racemosa, Scrophularia scorodonia, Scrophularia umbrosa, Scrophularia variegata, Stachys grandidentata, Stachys iberica, Stachys recta, Stachys spinosa, Stachys sylvatica, Stachys tetragona, Teucrium orientale, Verbascum lychnitis and Verbascum thapsus. 2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol was first documented in 2021 (PMID: 34688170). Based on a literature review a small amount of articles have been published on Harpagide (PMID: 35684573) (PMID: 35648096) (PMID: 35529931) (PMID: 34661766).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207562D          

 25 27  0  0  1  0            999 V2000
    1.4743   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8371    0.5350    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
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  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
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
  2 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -1.9088    1.6475   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.3046   -0.7915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7264   -0.1391   -2.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9884    0.4939   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055   -0.9150    0.1558 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3693   -0.9498    1.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0252   -1.1843    0.9713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9078   -2.5229    1.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1451   -0.3756    2.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833    0.1719    2.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750   -0.0278    2.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601   -0.3760    0.7673 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1104    0.6414    0.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    0.1857    0.0312 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3655    0.8628    0.7658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890    0.9206    0.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7162    1.0770    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701    0.0184    2.0299 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.3098   -0.6967 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1730   -0.0942   -1.2566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357   -0.4118   -1.8554 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4384    0.2376   -2.9816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    0.2800   -1.4591 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6456    1.6137   -1.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9040   -0.6993    0.0360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0915    1.5986   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740    2.1293    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6837    2.3180   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9395   -1.0925   -2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0543    1.2119    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.7372   -1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3933   -1.5835   -0.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1804   -1.3696    0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5641   -2.7145    2.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1342   -0.2261    2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1658    0.7871    3.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062   -1.2727    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5336   -0.8983    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140    1.7878   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6651    1.0565    0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785    2.0619    1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4971    0.3406    2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -1.2332   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7825   -0.8401   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7798   -1.4814   -2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595    1.2132   -2.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211   -0.2509   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2519    2.1721   -1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -1.5989   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  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
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  1  0
 25  2  1  0
 25  7  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  1
 14 38  1  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
 21 45  1  6
 22 46  1  0
 23 47  1  6
 24 48  1  0
 25 49  1  6
M  END


  Mrv1652309042207562D          

 25 27  0  0  1  0            999 V2000
    1.4743   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8371    0.5350    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
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  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
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
  2 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)CC(O)[C@]2(O)C=COC(OC3OC(CO)C(O)C(O)C3O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6?,7?,8?,9?,10?,11?,12?,13?,14-,15+/m0/s1

> <INCHI_KEY>
XUWSHXDEJOOIND-RARWZQNPSA-N

> <FORMULA>
C15H24O10

> <MOLECULAR_WEIGHT>
364.347

> <EXACT_MASS>
364.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.79778496476409

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(4aS,7S)-4a,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-4.202633549999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.774164501389873

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.117364889911116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760235146

> <JCHEM_POLAR_SURFACE_AREA>
169.29999999999998

> <JCHEM_REFRACTIVITY>
79.20390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.752  -3.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.792  -3.319   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.429   0.999   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   25                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   25                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Myoporoside	MeSH
Ajugol	MeSH
Leonuride	MeSH

Chemical Formula

C₁₅H₂₄O₁₀

Average Mass

364.3470 Da

Monoisotopic Mass

364.13695 Da

IUPAC Name

2-{[(4aS,7S)-4a,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[(4aS,7S)-4a,5,7-trihydroxy-7-methyl-1H,5H,6H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CC(O)[C@]2(O)C=COC(OC3OC(CO)C(O)C(O)C3O)C12

InChI Identifier

InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6?,7?,8?,9?,10?,11?,12?,13?,14-,15+/m0/s1

InChI Key

XUWSHXDEJOOIND-RARWZQNPSA-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 nipponensis	LOTUS Database	35616633
Ajuga pyramidalis	LOTUS Database	35616633
Ajuga reptans	LOTUS Database	35616633
Ajuga taiwanensis	LOTUS Database	35616633
Angelonia integerrima	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Caryopteris incana	LOTUS Database	35616633
Caryopteris mongholica	LOTUS Database	35616633
Clerodendrum indicum	LOTUS Database	35616633
Harpagophytum procumbens	LOTUS Database	35616633
Harpagophytum zeyheri	LOTUS Database	35616633
Lagochilus platycalyx	LOTUS Database	35616633
Lamiastrum galeobdolon	LOTUS Database	35616633
Penstemon serrulatus	LOTUS Database	35616633
Phlomoides tuberosa	LOTUS Database	35616633
Rogeria adenophylla	LOTUS Database	35616633
Scrophularia canina	LOTUS Database	35616633
Scrophularia ilwensis	LOTUS Database	35616633
Scrophularia leucoclada	LOTUS Database	35616633
Scrophularia ningpoensis	LOTUS Database	35616633
Scrophularia nodosa	LOTUS Database	35616633
Scrophularia racemosa	LOTUS Database	35616633
Scrophularia scorodonia	LOTUS Database	35616633
Scrophularia umbrosa	LOTUS Database	35616633
Scrophularia variegata	LOTUS Database	35616633
Stachys grandidentata	LOTUS Database	35616633
Stachys iberica	LOTUS Database	35616633
Stachys recta	LOTUS Database	35616633
Stachys spinosa	LOTUS Database	35616633
Stachys sylvatica	LOTUS Database	35616633
Stachys tetragona	LOTUS Database	35616633
Teucrium orientale	LOTUS Database	35616633
Verbascum lychnitis	LOTUS Database	35616633
Verbascum thapsus	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
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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
logP	-4.2	ChemAxon
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.2 m³·mol⁻¹	ChemAxon
Polarizability	34.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00010569

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

145706031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gxaba N, Manganyi MC: The Fight against Infection and Pain: Devil's Claw (Harpagophytum procumbens) a Rich Source of Anti-Inflammatory Activity: 2011-2022. Molecules. 2022 Jun 6;27(11). pii: molecules27113637. doi: 10.3390/molecules27113637. [PubMed:35684573 ]
Frezza C, Bozzato G, Sciubba F, Serafini I, Franceschin M, Curini R, Cianfaglione K, Venditti A, Bianco A, Serafini M, Foddai S: Phytochemical analysis on the aerial parts of Teucrium capitatum L. with aspects of chemosystematics and ethnobotany. Nat Prod Res. 2022 Jun 1:1-10. doi: 10.1080/14786419.2022.2081967. [PubMed:35648096 ]
Sun KH, Yang MF, Xu XR, Li Y, Gao Z, Zhang QY, Li H, Wang SQ, Lou LX, Wu AM, Jin QS, Wu SX, Nie B: Comparative Pharmacokinetics of Seven Major Compounds in Normal and Atherosclerosis Mice after Oral Administration of Simiao Yong'an Decoction. Evid Based Complement Alternat Med. 2022 Apr 28;2022:4604601. doi: 10.1155/2022/4604601. eCollection 2022. [PubMed:35529931 ]
Erukainure OL, Atolani O, Muhammad A, Ravichandran R, Abarshi MM, Katsayal SB, Chukwuma CI, Preissner R, Banerjee P, Mesaik MA: Translational suppression of SARS-COV-2 ORF8 protein mRNA as a Viable therapeutic target against COVID-19: Computational studies on potential roles of isolated compounds from Clerodendrum volubile leaves. Comput Biol Med. 2021 Dec;139:104964. doi: 10.1016/j.compbiomed.2021.104964. Epub 2021 Oct 19. [PubMed:34688170 ]
Ullah MA, Gul FZ, Khan T, Bajwa MN, Drouet S, Tungmunnithum D, Giglioli-Guivarc'h N, Liu C, Hano C, Abbasi BH: Differential induction of antioxidant and anti-inflammatory phytochemicals in agitated micro-shoot cultures of Ajuga integrifolia Buch. Ham. ex D.Don with biotic elicitors. AMB Express. 2021 Oct 18;11(1):137. doi: 10.1186/s13568-021-01297-3. [PubMed:34661766 ]
LOTUS database [Link]

Showing NP-Card for 2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0189456)

MOL for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0189456 (2-{[(4as,7s)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)