NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0254626)

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Record Information

Version

2.0

Created at

2022-09-07 18:50:52 UTC

Updated at

2022-09-07 18:50:52 UTC

NP-MRD ID

NP0254626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Thunaloside 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. (2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Thunbergia alata and Thunbergia grandiflora. Based on a literature review very few articles have been published on Thunaloside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220502D          

 24 26  0  0  1  0            999 V2000
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24  3  1  6  0  0  0
  7 24  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    2.4461    2.2493    1.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786    1.6327    1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6529    0.8632   -0.0758 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6733    0.2082   -0.9710 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8306    0.9656   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9809   -1.1354   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -1.3230    0.7723 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5345   -2.7172    0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6009   -3.0623   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1348   -2.0563   -0.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -0.8023   -0.3371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3482   -0.9289    0.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420   -0.1166   -0.1503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8158    0.8200    0.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0815    1.2640    0.6038 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8318    0.8241    1.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149    1.3723    3.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8625    0.9773   -0.6166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2704    2.1503   -1.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2383    0.0452   -1.5986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1110   -0.5232   -2.4823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -0.9661   -0.7947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8708   -1.9391   -1.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -0.3123    0.5642 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5457    3.2349    1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    2.3965    0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9520    0.9068    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    1.5227   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336    0.1427   -1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    1.5987   -1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368   -1.8907   -1.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0407   -1.1521   -0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985   -1.1078    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -3.4501    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216   -4.0979   -0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.0605   -1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8879    0.4310   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435    2.3930    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8649    1.1891    1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.2752    2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8893    1.4546    3.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    0.5016   -0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    2.6747   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4761    0.6341   -2.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439   -1.4966   -2.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0914   -1.3745   -0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -1.7338   -2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    0.0695    1.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24  3  1  0
 24  7  1  0
 22 13  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  6
  4 29  1  6
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  9 35  1  0
 11 36  1  6
 13 37  1  6
 15 38  1  1
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  6
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  1
M  END


  Mrv1652309072220502D          

 24 26  0  0  1  0            999 V2000
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24  3  1  6  0  0  0
  7 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1[C@@H](O)C[C@@H]2C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O9/c16-4-7-8(18)3-6-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-2,6-21H,3-5H2/t6-,7-,8-,9+,10-,11+,12-,13+,14-,15-/m0/s1

> <INCHI_KEY>
GCWUDVRYCRPVLH-JWCVOPGOSA-N

> <FORMULA>
C15H24O9

> <MOLECULAR_WEIGHT>
348.348

> <EXACT_MASS>
348.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.1067412312496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.0465486139999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.187370270061734

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205724593027517

> <JCHEM_PKA_STRONGEST_BASIC>
-2.63632977321958

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
78.536

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₉

Average Mass

348.3480 Da

Monoisotopic Mass

348.14203 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1[C@@H](O)C[C@@H]2C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

InChI Identifier

InChI=1S/C15H24O9/c16-4-7-8(18)3-6-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-2,6-21H,3-5H2/t6-,7-,8-,9+,10-,11+,12-,13+,14-,15-/m0/s1

InChI Key

GCWUDVRYCRPVLH-JWCVOPGOSA-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
Thunbergia alata	LOTUS Database	35616633
Thunbergia grandiflora	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
Monoterpenoid
Bicyclic monoterpenoid
Oxane
Monosaccharide
Cyclic alcohol
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
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	-3	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.54 m³·mol⁻¹	ChemAxon
Polarizability	34.11 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

101664502

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0254626)

MOL for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0254626 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7s,7as)-6-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)