NP-MRD: Showing NP-Card for Geniposidic acid (NP0057478)

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Record Information

Version

2.0

Created at

2022-04-28 02:54:38 UTC

Updated at

2022-04-28 02:54:38 UTC

NP-MRD ID

NP0057478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geniposidic acid

Description

(1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid 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 found in Adina polycephala Benth, Afrocanthium gilfillanii, Cordiera sessilis, Aloysia citrodora, Antonia ovata, Avicennia marina, Avicennia officinalis L. , Canthium berberidifolium, Castilleja tenuiflora, Cistanche salsa, Cistanche tubulosa , Cordylanthus tenuis, Cruciata laevipes, Erinus alpinus, Eucommia ulmoides, Eucommia ulmoides Oliv. , Euphrasia nemorosa, Euphrasia pectinata, Euphrasia salisburgensis, Galium album, Galium humifusum, Galium lovcense, Galium mirum, Galium mollugo, Galium rivale, Gardenia jasminoides , Garrya elliptica, Genipa americana , Globularia orientalis, Globularia trichosantha, Gmelina philippensis , Diodella teres, Leonotis nepetifolia, Lippia alba , Orthocarpus luteus, Pedicularis artselaeri, Pedicularis kansuensis, Pedicularis longiflora, Pedicularis muscicola, Pedicularis nordmanniana, Pedicularis plicata, Pedicularis verticillata, Penstemon barbatus, Penstemon barrettiae, Penstemon crandallii, Penstemon rydbergii, Penstemon virens, Phtheirospermum japonicum, Plantago alpina, Plantago asiatica , Plantago bellardi, Plantago lundborgii, Plantago major , Plantago raoulii, Plocama calabrica, Rehmannia glutinosa , Scrophularia dentata, Scyphiphora hydrophyllacea, Veronica anagallis-aquatica and Veronica bellidioides. Based on a literature review very few articles have been published on (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204542D          

 26 28  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.6021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4990    2.1896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  6  0  0  0
 11 10  1  1  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
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 15 18  1  6  0  0  0
 14 19  1  1  0  0  0
 13 20  1  6  0  0  0
 20 21  1  0  0  0  0
  2 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -4.5934    2.8988    2.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    2.5756    2.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    3.0720    4.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6091    1.6663    2.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653    1.3530    2.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5918    0.5152    2.0015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851    0.0136    0.6536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0672   -1.1112    0.4531 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895   -0.9704   -0.2831 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0916   -1.1075    0.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2872   -0.5607    0.3772 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3437    0.9349    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    1.2633    1.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360   -0.9541   -1.0222 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0026   -1.1943   -1.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9196   -2.2820   -1.3047 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3323   -2.6925   -2.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -1.9441   -1.3254 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2419   -1.4095   -2.6272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327   -0.1434    0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6579   -0.2441   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8152   -1.4868   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431   -2.1916   -1.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    0.9960   -1.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259    1.9958   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997    1.1232    0.7892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1389    4.0744    4.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1695    1.7657    3.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389    0.8194    0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2115    0.0809   -0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0655   -1.0058    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532    1.3384    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6214    1.4195   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1164    0.4090    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.1630   -1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4948   -0.3591   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -2.9888   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0106   -1.9842   -3.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039   -2.9267   -1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -0.6404   -2.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6731   -0.9487    1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1584   -1.2682   -2.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5733   -2.1752   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255   -2.8056   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    1.2381   -2.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    2.8185   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983    2.3166   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0704    0.8697    0.7066 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  6
  7 29  1  6
  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  1
  3 27  1  0
 18 39  1  6
 19 40  1  0
 16 37  1  1
 17 38  1  0
 14 35  1  6
 15 36  1  0
M  END


  Mrv1652304282204542D          

 26 28  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.6021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4990    2.1896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  6  0  0  0
 11 10  1  1  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
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 15 18  1  6  0  0  0
 14 19  1  1  0  0  0
 13 20  1  6  0  0  0
 20 21  1  0  0  0  0
  2 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057478

> <DATABASE_NAME>
NP-MRD

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

> <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)/t7-,9-,10-,11-,12+,13+,15+,16-/m1/s1

> <INCHI_KEY>
ZJDOESGVOWAULF-RGHCVXNGSA-N

> <FORMULA>
C16H22O10

> <MOLECULAR_WEIGHT>
374.342

> <EXACT_MASS>
374.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.95897162144045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-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>
166.14000000000001

> <JCHEM_REFRACTIVITY>
83.7375

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-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                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.864  -0.533   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.864  -5.153   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.197  -5.153   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.864   2.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.864   4.087   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.198   4.857   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.531   4.087   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.531   2.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.865   1.777   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.865   4.857   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.198   6.397   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.531   7.167   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.250   1.728   0.000  0.00  0.00           O+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22    2   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23    1                                                       
CONECT   25   22   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,7as)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-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

374.3420 Da

Monoisotopic Mass

374.12130 Da

IUPAC Name

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

Traditional Name

(1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-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

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

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)/t7-,9-,10-,11-,12+,13+,15+,16-/m1/s1

InChI Key

ZJDOESGVOWAULF-RGHCVXNGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Adina polycephala Benth	Plant	KNApSAcK
Afrocanthium gilfillanii	LOTUS Database	35616633
Alibertia sessilis	LOTUS Database	35616633
Aloysia citrodora	LOTUS Database	35616633
Antonia ovata	LOTUS Database	35616633
Avicennia marina	LOTUS Database	35616633
Avicennia officinalis	Plant	KNApSAcK
Canthium berberidifolium	Plant	KNApSAcK
Castilleja tenuiflora	LOTUS Database	35616633
Cistanche salsa	LOTUS Database	35616633
Cistanche tubulosa	Plant	KNApSAcK
Cordylanthus tenuis	LOTUS Database	35616633
Cruciata laevipes	LOTUS Database	35616633
Erinus alpinus	Plant	KNApSAcK
Eucommia ulmoides	LOTUS Database	35616633
Eucommia ulmoides Oliv.	Plant	KNApSAcK
Euphrasia nemorosa	LOTUS Database	35616633
Euphrasia pectinata	LOTUS Database	35616633
Euphrasia salisburgensis	LOTUS Database	35616633
Galium album	LOTUS Database	35616633
Galium humifusum	LOTUS Database	35616633
Galium lovcense	LOTUS Database	35616633
Galium mirum	LOTUS Database	35616633
Galium mollugo	LOTUS Database	35616633
Galium rivale	Plant	KNApSAcK
Gardenia jasminoides	Plant	KNApSAcK
Garrya elliptica	LOTUS Database	35616633
Genipa americana	Plant	KNApSAcK
Globularia orientalis	LOTUS Database	35616633
Globularia trichosantha	Plant	KNApSAcK
Gmelina philippensis	Plant	KNApSAcK
Hexasepalum teres	LOTUS Database	35616633
Leonotis nepetifolia	LOTUS Database	35616633
Lippia alba	Plant	KNApSAcK
Orthocarpus luteus	LOTUS Database	35616633
Pedicularis artselaeri	LOTUS Database	35616633
Pedicularis kansuensis	LOTUS Database	35616633
Pedicularis longiflora	LOTUS Database	35616633
Pedicularis muscicola	Plant	KNApSAcK
Pedicularis nordmanniana	Plant	KNApSAcK
Pedicularis plicata	LOTUS Database	35616633
Pedicularis verticillata	LOTUS Database	35616633
Penstemon barbatus	LOTUS Database	35616633
Penstemon barrettiae	LOTUS Database	35616633
Penstemon crandallii	LOTUS Database	35616633
Penstemon rydbergii	LOTUS Database	35616633
Penstemon virens	LOTUS Database	35616633
Phtheirospermum japonicum	LOTUS Database	35616633
Plantago alpina	Plant	KNApSAcK
Plantago asiatica	Plant	KNApSAcK
Plantago bellardi	Plant	KNApSAcK
Plantago lundborgii	Plant	KNApSAcK
Plantago major	Plant	KNApSAcK
Plantago raoulii	Plant	KNApSAcK
Plocama calabrica	LOTUS Database	35616633
Rehmannia glutinosa	Plant	KNApSAcK
Scrophularia dentata	Plant	KNApSAcK
Scyphiphora hydrophyllacea	LOTUS Database	35616633
Veronica anagallis-aquatica	LOTUS Database	35616633
Veronica bellidioides	Plant	KNApSAcK

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
Vinylogous ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	34.96 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

Not Available

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

154496623

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Geniposidic acid (NP0057478)

MOL for NP0057478 (Geniposidic acid)

3D MOL for NP0057478 (Geniposidic acid)

3D SDF for NP0057478 (Geniposidic acid)

3D-SDF for NP0057478 (Geniposidic acid)

PDB for NP0057478 (Geniposidic acid)

3D PDB for NP0057478 (Geniposidic acid)

SMILES for NP0057478 (Geniposidic acid)

INCHI for NP0057478 (Geniposidic acid)

Structure for NP0057478 (Geniposidic acid)

3D Structure for NP0057478 (Geniposidic acid)