NP-MRD: Showing NP-Card for (1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0234697)

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Record Information

Version

2.0

Created at

2022-09-06 16:53:48 UTC

Updated at

2022-09-06 16:53:48 UTC

NP-MRD ID

NP0234697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid

Description

Theveside 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. (1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid is found in Cerbera manghas, Lantana camara, Lippia alba, Lippia javanica and Thevetia peruviana. (1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid was first documented in 2008 (PMID: 17705148). Based on a literature review a small amount of articles have been published on Theveside (PMID: 24805359) (PMID: 34333103) (PMID: 19500792).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062218532D          

 27 29  0  0  1  0            999 V2000
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -3.8253    4.9984   -0.7513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490    4.2299   -1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2639    4.4151   -2.8482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894    3.2018   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    3.0143    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    2.0298    0.8499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282    0.9403    0.0895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0905   -0.2448    0.7673 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653   -0.8344    1.1842 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2138   -2.1613    0.8087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4921   -2.6026    1.1025 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8267   -3.8957    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192   -4.2792    0.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -2.6710    2.6147 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8196   -3.2467    3.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -1.2166    3.0879 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7960   -1.0782    4.4206 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -0.8272    2.7311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3081    0.3760    3.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3885    0.8985   -1.2929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2965    0.4084   -2.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1239   -0.9898   -2.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -1.0679   -3.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    1.4377   -2.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215    2.6774   -1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227    2.3311   -1.8421 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9882    2.2409   -3.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5154    4.9326   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422    3.6644    0.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970    1.0447    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9499   -0.2393    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2506   -1.8426    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -3.7309   -0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -4.6760    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518   -3.9111    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -3.2381    2.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640   -2.5049    3.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974   -0.6356    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -0.4319    4.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -1.6907    3.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9561    0.1695    3.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    0.3355   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9982   -1.3232   -3.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -1.6878   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -1.7897   -4.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3486    1.3919   -3.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1658    3.5871   -2.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758    2.8521   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7604    1.6395   -3.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4 26  1  0
 26 27  1  6
 26 25  1  0
 25 24  1  0
 24 21  2  0
 21 22  1  0
 22 23  1  0
 21 20  1  0
  9 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 11  1  0
 20  7  1  0
 20 26  1  0
 13 35  1  0
 12 33  1  0
 12 34  1  0
 11 32  1  6
  9 31  1  6
  7 30  1  6
  5 29  1  0
  3 28  1  0
 27 49  1  0
 25 47  1  0
 25 48  1  0
 24 46  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 20 42  1  1
 18 40  1  1
 19 41  1  0
 16 38  1  6
 17 39  1  0
 14 36  1  1
 15 37  1  0
M  END


  Mrv1652309062218532D          

 27 29  0  0  1  0            999 V2000
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0234697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2OC=C(C(O)=O)[C@@]3(O)CC=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O11/c17-3-6-1-2-16(24)7(13(22)23)5-25-14(9(6)16)27-15-12(21)11(20)10(19)8(4-18)26-15/h1,5,8-12,14-15,17-21,24H,2-4H2,(H,22,23)/t8-,9+,10-,11+,12-,14+,15+,16+/m1/s1

> <INCHI_KEY>
KKGHSVKNCUMEEN-XKUHUSTMSA-N

> <FORMULA>
C16H22O11

> <MOLECULAR_WEIGHT>
390.341

> <EXACT_MASS>
390.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.20541412008768

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.4921793086666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.191475616566091

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.065139873108093

> <JCHEM_PKA_STRONGEST_BASIC>
-2.737507588664882

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
84.90479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.340  -2.261   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   26                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    4   20   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

C₁₆H₂₂O₁₁

Average Mass

390.3410 Da

Monoisotopic Mass

390.11621 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C(C(O)=O)[C@@]3(O)CC=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H22O11/c17-3-6-1-2-16(24)7(13(22)23)5-25-14(9(6)16)27-15-12(21)11(20)10(19)8(4-18)26-15/h1,5,8-12,14-15,17-21,24H,2-4H2,(H,22,23)/t8-,9+,10-,11+,12-,14+,15+,16+/m1/s1

InChI Key

KKGHSVKNCUMEEN-XKUHUSTMSA-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
Cerbera manghas	LOTUS Database	35616633
Lantana camara	LOTUS Database	35616633
Lippia alba	LOTUS Database	35616633
Lippia javanica	LOTUS Database	35616633
Thevetia peruviana	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
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
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

C00010719

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

25085768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gorantla JN, Vellekkatt J, Nath LR, Anto RJ, Lankalapalli RS: Cytotoxicity studies of semi-synthetic derivatives of theveside derived from the aqueous extract of leaves of 'suicide tree' Cerbera odollam. Nat Prod Res. 2014;28(18):1507-12. doi: 10.1080/14786419.2014.913242. Epub 2014 May 8. [PubMed:24805359 ]
Hennebelle T, Sahpaz S, Gressier B, Joseph H, Bailleul F: Antioxidant and neurosedative properties of polyphenols and iridoids from Lippia alba. Phytother Res. 2008 Feb;22(2):256-8. doi: 10.1002/ptr.2266. [PubMed:17705148 ]
Lencina JDS, Bonfa Moslaves IS, de Araujo Isaias Muller J, Carvalho R, Amianti C, Bonfim I, Alves FM, Carollo CA, Candeloro L, Alves Dos Santos Junior A, Brentan da Silva D, Toffoli Kadri MC: Lantana canescens (Kunth) inhibits inflammatory and hyperalgesic responses in murine models. J Ethnopharmacol. 2021 Nov 15;280:114461. doi: 10.1016/j.jep.2021.114461. Epub 2021 Jul 29. [PubMed:34333103 ]
Quirantes-Pine R, Funes L, Micol V, Segura-Carretero A, Fernandez-Gutierrez A: High-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight and ion-trap tandem mass spectrometry to identify phenolic compounds from a lemon verbena extract. J Chromatogr A. 2009 Jul 10;1216(28):5391-7. doi: 10.1016/j.chroma.2009.05.038. Epub 2009 May 21. [PubMed:19500792 ]
LOTUS database [Link]

Showing NP-Card for (1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0234697)

MOL for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D MOL for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D SDF for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D-SDF for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

PDB for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D PDB for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

SMILES for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

INCHI for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

Structure for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D Structure for NP0234697 ((1s,4ar,7ar)-4a-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)