NP-MRD: Showing NP-Card for (1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid (NP0175838)

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Record Information

Version

2.0

Created at

2022-09-03 13:24:12 UTC

Updated at

2022-09-03 13:24:12 UTC

NP-MRD ID

NP0175838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Ixoside 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. Thus, ixoside is considered to be an isoprenoid. (1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid is found in Alibertia edulis, Antonia ovata and Leonotis nepetifolia. (1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid was first documented in 2006 (PMID: 29435882). Based on a literature review a significant number of articles have been published on Ixoside (PMID: 20707194) (PMID: 20715141) (PMID: 35129017) (PMID: 26434124) (PMID: 21815402) (PMID: 16792422).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032215242D          

 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
    2.0769   -1.6527    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
  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  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
  4 27  1  0  0  0  0
 20 27  1  0  0  0  0
M  END

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
   -5.9544   -1.7343   -0.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9729   -2.4553    0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1726   -3.8072    0.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352   -1.8879    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5783   -2.6173    0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.0354    0.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -0.7892    0.0379 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1219   -1.0117   -0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2109   -0.3759   -0.2341 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7783    0.5632   -1.0929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    1.3662   -0.3458 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2452    2.4432   -1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941    3.2501   -1.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7793    0.6030    0.2554 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4565    1.4711    1.1074 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487   -0.5629    1.0719 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2940   -1.3498    1.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288   -1.3419    0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8309   -2.4888    0.7440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1149   -0.1382   -0.7363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0191    1.3294   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185    2.2825   -1.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775    3.5019   -1.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6710    1.8922   -2.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6627    1.6054    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2507    0.3423    1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313   -0.4586   -0.0575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4922   -4.5193    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866   -3.6746    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765   -0.1507    0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9638    0.1775    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    1.8710    0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8944    3.0489   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9175    1.9544   -1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106    4.1823   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578    0.2209   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    0.9534    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -0.1387    1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796   -2.2003    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934   -1.5640   -0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -2.6033    1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1055   -0.3647   -1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    2.2104   -3.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    2.5693    1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -0.1096    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1962    0.5180    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825    0.0230   -0.5773 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 27  1  0
 27 26  1  0
 26 25  1  0
 25 21  2  0
 21 20  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  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 27  1  0
 13 35  1  0
 12 33  1  0
 12 34  1  0
 11 32  1  1
  9 31  1  1
  7 30  1  1
  5 29  1  0
 27 47  1  6
 26 45  1  0
 26 46  1  0
 25 44  1  0
 20 42  1  6
 24 43  1  0
  3 28  1  0
 18 40  1  6
 19 41  1  0
 16 38  1  1
 17 39  1  0
 14 36  1  6
 15 37  1  0
M  END

  Mrv1652309032215242D          

 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
    2.0769   -1.6527    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
  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  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
  4 27  1  0  0  0  0
 20 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175838

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O11/c17-3-8-10(18)11(19)12(20)16(26-8)27-15-9-5(1-2-6(9)13(21)22)7(4-25-15)14(23)24/h2,4-5,8-12,15-20H,1,3H2,(H,21,22)(H,23,24)/t5-,8-,9+,10-,11+,12-,15+,16+/m1/s1

> <INCHI_KEY>
AYRQUPRKTDTPEN-SQQPMCIGSA-N

> <FORMULA>
C16H20O11

> <MOLECULAR_WEIGHT>
388.325

> <EXACT_MASS>
388.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.67732782807122

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.41

> <JCHEM_LOGP>
-2.1214949389999993

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.32718269554646

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6290635515476963

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615683995

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
83.67999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
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   27                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    4   20                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₁₁

Average Mass

388.3250 Da

Monoisotopic Mass

388.10056 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H20O11/c17-3-8-10(18)11(19)12(20)16(26-8)27-15-9-5(1-2-6(9)13(21)22)7(4-25-15)14(23)24/h2,4-5,8-12,15-20H,1,3H2,(H,21,22)(H,23,24)/t5-,8-,9+,10-,11+,12-,15+,16+/m1/s1

InChI Key

AYRQUPRKTDTPEN-SQQPMCIGSA-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
Alibertia edulis	LOTUS Database	35616633
Antonia ovata	LOTUS Database	35616633
Leonotis nepetifolia	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
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	-1.4	ALOGPS
logP	-2.1	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.68 m³·mol⁻¹	ChemAxon
Polarizability	35.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

C00010582

Chemspider ID

24708118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44583801

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sinaphet B, Noiarsa P, Rujirawat S, Otsuka H, Kanchanapoom T: Dolichandroside, a new phenolic triglycoside from Dolichandrone serrulata (DC.) Seem. J Nat Med. 2006 Jul;60(3):251-254. doi: 10.1007/s11418-006-0043-5. Epub 2006 Apr 14. [PubMed:29435882 ]
Zhang Y, Gan M, Li S, Wang S, Zhu C, Yang Y, Hu J, Chen N, Shi J: [Chemical constituents of stems and branches of Adina polycephala]. Zhongguo Zhong Yao Za Zhi. 2010 May;35(10):1261-71. doi: 10.4268/cjcmm20101010. [PubMed:20707194 ]
Quirantes-Pine R, Arraez-Roman D, Segura-Carretero A, Fernandez-Gutierrez A: Characterization of phenolic and other polar compounds in a lemon verbena extract by capillary electrophoresis-electrospray ionization-mass spectrometry. J Sep Sci. 2010 Sep;33(17-18):2818-27. doi: 10.1002/jssc.201000228. [PubMed:20715141 ]
Singh M, Hirlekar BU, Mondal S, Pant S, Dhaked DK, Ravichandiran V, Hazra A, Bharitkar YP: Isolation of phytochemicals from Dolichandrone atrovirens followed by semisynthetic modification of ixoside via azomethine ylide cycloaddition; computational approach towards chemo-selection. Nat Prod Res. 2022 Feb 6:1-10. doi: 10.1080/14786419.2022.2037084. [PubMed:35129017 ]
Phanthong P, Phumal N, Chancharunee S, Mangmool S, Anantachoke N, Bunyapraphatsara N: Biological Activity of Dolichandrone serrulata Flowers and Their Active Components. Nat Prod Commun. 2015 Aug;10(8):1387-90. [PubMed:26434124 ]
Dinda B, Debnath S, Banik R, Sato N, Harigaya Y: Iridoid glucosides from Wendlandia tinctoria roots. Nat Prod Commun. 2011 Jun;6(6):747-8. [PubMed:21815402 ]
Yang XW, Ma YL, He HP, Wang YH, Di YT, Zhou H, Li L, Hao XJ: Iridoid constituents of Tarenna attenuata. J Nat Prod. 2006 Jun;69(6):971-4. doi: 10.1021/np0600301. [PubMed:16792422 ]
LOTUS database [Link]

Showing NP-Card for (1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid (NP0175838)

MOL for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

3D MOL for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

3D SDF for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

3D-SDF for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

PDB for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

3D PDB for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

SMILES for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

INCHI for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

Structure for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)

3D Structure for NP0175838 ((1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4,7-dicarboxylic acid)