NP-MRD: Showing NP-Card for 7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0169493)

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Record Information

Version

2.0

Created at

2022-09-03 05:27:21 UTC

Updated at

2022-09-03 05:27:21 UTC

NP-MRD ID

NP0169493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Geniposidic acid, also known as geniposidate, 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. Geniposidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Geniposidic acid is a natural chemical compound, classified as an iridoid glucoside, found in a variety of plants including Eucommia ulmoides and Gardenia jasminoides. Outside of the human body, Geniposidic acid has been detected, but not quantified in, beverages and fruits. 7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid is found in Cordiera sessilis, Antonia ovata, Cistanche tubulosa, Cordylanthus kingii, Eucommia ulmoides, Euphrasia pectinata, Euphrasia salisburgensis, Galium mollugo, Galium rivale, Gardenia jasminoides, Garrya elliptica, Genipa americana, Pedicularis longiflora, Pedicularis verticillata, Plantago alpina, Plantago asiatica, Plantago bellardii, Plocama calabrica, Rehmannia glutinosa, Scyphiphora hydrophyllacea, Veronica anagallis-aquatica and Veronica kellereri. This could make geniposidic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308082D          

 26 28  0  0  0  0            999 V2000
    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
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    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
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   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
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   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
    5.4223   -4.1250    0.0000 O   0  0  0  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
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   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
    3.9934    2.4750    0.0000 O   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
    3.9934   -2.4750    0.0000 O   0  0  0  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
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  3  1  0  0  0  0
 18  4  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  2  0  0  0  0
 23 14  1  0  0  0  0
 24  5  1  0  0  0  0
 24 15  1  0  0  0  0
 25  9  1  0  0  0  0
 25 16  1  0  0  0  0
 26 15  1  0  0  0  0
 26 16  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    4.2055    3.1918   -3.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2814    2.5001   -2.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693    2.1766   -1.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1136    2.0919   -1.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9151    2.4309   -1.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646    2.0461   -1.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176    0.8904   -0.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2514    0.0064   -0.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3567   -0.1183   -0.0361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5079   -1.3487    0.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042   -1.8319    0.8524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0008   -1.3903    2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0282   -0.0121    2.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8774   -1.4540    0.0131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4945   -2.6138   -0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5064   -0.6303   -1.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6731   -0.0087   -1.6409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649    0.4567   -0.7323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1549    1.1262   -1.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454    0.2809   -0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4102   -0.5593    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545   -1.3211    1.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175   -0.5150    2.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7475   -0.5839    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3073    0.2800   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880    1.3098   -0.3032 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0409    2.7236   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    3.0203   -2.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024    1.2608    0.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.5777    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6329   -2.9607    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2193   -1.7983    2.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -1.7706    2.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.3200    2.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6318   -0.8769    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1122   -2.9986    0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0664   -1.2018   -2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884   -0.4747   -1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0646    1.1595   -0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700    0.4500   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -0.3253   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -2.0931    1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -1.8502    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6764   -0.7695    3.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.1257    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2810    0.6954   -0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687   -0.2596   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    1.8971    0.6134 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 26  1  0
 26 25  1  0
 25 24  1  0
 24 21  2  0
 21 22  1  0
 22 23  1  0
 21 20  1  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 26  1  0
 13 34  1  0
 12 32  1  0
 12 33  1  0
 11 31  1  1
  9 30  1  1
  7 29  1  1
  5 28  1  0
 26 48  1  1
 25 46  1  0
 25 47  1  0
 24 45  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 20 41  1  6
  3 27  1  0
 18 39  1  1
 19 40  1  0
 16 37  1  6
 17 38  1  0
 14 35  1  1
 15 36  1  0
M  END


  Mrv0541 05061308082D          

 26 28  0  0  0  0            999 V2000
    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
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    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
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   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
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   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
    5.4223   -4.1250    0.0000 O   0  0  0  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
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   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
    3.9934    2.4750    0.0000 O   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
    3.9934   -2.4750    0.0000 O   0  0  0  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
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  3  1  0  0  0  0
 18  4  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  2  0  0  0  0
 23 14  1  0  0  0  0
 24  5  1  0  0  0  0
 24 15  1  0  0  0  0
 25  9  1  0  0  0  0
 25 16  1  0  0  0  0
 26 15  1  0  0  0  0
 26 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169493

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=C(C3CC=C(CO)C23)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)

> <INCHI_KEY>
ZJDOESGVOWAULF-UHFFFAOYSA-N

> <FORMULA>
C16H22O10

> <MOLECULAR_WEIGHT>
374.3399

> <EXACT_MASS>
374.121296924

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
35.581434963574196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.71

> <JCHEM_LOGP>
-2.593958694666666

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.20651525461768

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.222503321747324

> <JCHEM_PKA_STRONGEST_BASIC>
-2.735421632953014

> <JCHEM_POLAR_SURFACE_AREA>
166.13999999999996

> <JCHEM_REFRACTIVITY>
83.73750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.788  -6.930   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  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.122  -7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.455  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.454  -4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    6   17                                                       
CONECT    4    9   18                                                       
CONECT    5    8   24                                                       
CONECT    6    1    3   10                                                  
CONECT    7    2    8   10                                                  
CONECT    8    5    7   14                                                  
CONECT    9    4   11   25                                                  
CONECT   10    6    7   15                                                  
CONECT   11    9   12   19                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   16   21                                                  
CONECT   14    8   22   23                                                  
CONECT   15   10   24   26                                                  
CONECT   16   13   25   26                                                  
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   14                                                            
CONECT   24    5   15                                                       
CONECT   25    9   16                                                       
CONECT   26   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Geniposidate	Generator
7-(Hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator

Chemical Formula

C₁₆H₂₂O₁₀

Average Mass

374.3399 Da

Monoisotopic Mass

374.12130 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=C(C3CC=C(CO)C23)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)

InChI Key

ZJDOESGVOWAULF-UHFFFAOYSA-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 sessilis	LOTUS Database	35616633
Antonia ovata	LOTUS Database	35616633
Cistanche tubulosa	LOTUS Database	35616633
Cordylanthus kingii	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Euphrasia pectinata	LOTUS Database	35616633
Euphrasia salisburgensis	LOTUS Database	35616633
Galium mollugo	LOTUS Database	35616633
Galium rivale	LOTUS Database	35616633
Gardenia jasminoides	LOTUS Database	35616633
Garrya elliptica	LOTUS Database	35616633
Genipa americana	LOTUS Database	35616633
Pedicularis longiflora	LOTUS Database	35616633
Pedicularis verticillata	LOTUS Database	35616633
Plantago alpina	LOTUS Database	35616633
Plantago asiatica	LOTUS Database	35616633
Plantago bellardii	LOTUS Database	35616633
Plocama calabrica	LOTUS Database	35616633
Rehmannia glutinosa	LOTUS Database	35616633
Scyphiphora hydrophyllacea	LOTUS Database	35616633
Veronica anagallis-aquatica	LOTUS Database	35616633
Veronica kellereri	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
Secondary alcohol
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Primary alcohol
Organooxygen compound
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	-1.7	ALOGPS
logP	-2.6	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.74 m³·mol⁻¹	ChemAxon
Polarizability	35.58 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

HMDB0034942

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Geniposidic acid

METLIN ID

Not Available

PubChem Compound

323273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0169493)

MOL for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D MOL for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D SDF for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D-SDF for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

PDB for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D PDB for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

SMILES for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

INCHI for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

Structure for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D Structure for NP0169493 (7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid)