NP-MRD: Showing NP-Card for methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0283876)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 11:19:35 UTC

Updated at

2022-09-09 11:19:35 UTC

NP-MRD ID

NP0283876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Caryoptoside 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. methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Lamium album, Lippia graveolens, Pedicularis artselaeri, Pedicularis muscicola, Pedicularis verticillata and Plantago sempervirens. methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate was first documented in 2012 (PMID: 22081901). Based on a literature review a small amount of articles have been published on Caryoptoside (PMID: 26197306) (PMID: 22424117).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213192D          

 28 30  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   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    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  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
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -5.6522    3.9573    1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133    3.4329    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2983    2.0900    0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1782    1.2970    0.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481    1.5313   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.3410   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228    1.6825   -1.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113    0.5373   -0.7060 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6262    0.8892   -0.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    0.3872   -0.4239 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3410   -0.4150    0.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3854   -1.1980    0.1560 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8613   -2.0207    1.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258   -2.8468    0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5512   -0.2754   -0.2135 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6758   -0.9785   -0.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    0.6056   -1.3349 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0018    1.5450   -1.7282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8680    1.3863   -0.7817 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4973    2.2669   -1.7755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -0.1306    0.1935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8495    0.1249   -0.3923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6725   -0.8530    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -2.1202    0.1551 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1580   -3.0915    1.1064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429   -1.6164    0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5352   -2.3120   -0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0213   -1.9688    1.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5618    3.9308    2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7321    5.0457    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5790    3.4164    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    3.4150   -0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -0.1508   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379   -0.2757   -1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -1.8132   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2180   -1.3579    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0517   -2.7085    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295   -2.6593    1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6996    0.3832    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4624   -0.3870   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774   -0.0013   -2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0285    2.2220   -0.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2414    1.8953    0.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    1.7527   -2.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574    0.3319    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8764   -0.1702   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7652   -0.6079    1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6642   -0.9325   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0432   -2.4580   -0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223   -3.6282    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385   -2.1230   -1.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5239   -2.2099   -0.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459   -3.4161   -0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0660   -1.7412    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  1
 22  5  1  0
 19 10  1  0
 26 21  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  8 33  1  6
 10 34  1  6
 12 35  1  6
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  1
 16 40  1  0
 17 41  1  6
 18 42  1  0
 19 43  1  1
 20 44  1  0
 21 45  1  1
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  6
 25 50  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 28 54  1  0
M  END


  Mrv1652309092213192D          

 28 30  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   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    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  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
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0283876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C1C[C@H](O)[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O11/c1-17(24)9(19)3-6-7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8-13,15-16,18-22,24H,3-4H2,1-2H3/t6?,8-,9+,10?,11-,12+,13-,15+,16+,17+/m1/s1

> <INCHI_KEY>
VIXATJMNFXMPDC-BEZJANDHSA-N

> <FORMULA>
C17H26O11

> <MOLECULAR_WEIGHT>
406.384

> <EXACT_MASS>
406.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.92623808631035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.7353660783333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.040990653685132

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.184936386756295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601928367

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
88.64169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.627  -1.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   26                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   21   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆O₁₁

Average Mass

406.3840 Da

Monoisotopic Mass

406.14751 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C1C[C@H](O)[C@]2(C)O

InChI Identifier

InChI=1S/C17H26O11/c1-17(24)9(19)3-6-7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8-13,15-16,18-22,24H,3-4H2,1-2H3/t6?,8-,9+,10?,11-,12+,13-,15+,16+,17+/m1/s1

InChI Key

VIXATJMNFXMPDC-BEZJANDHSA-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
Lamium album	LOTUS Database	35616633
Lippia graveolens	LOTUS Database	35616633
Pedicularis artselaeri	LOTUS Database	35616633
Pedicularis muscicola	LOTUS Database	35616633
Pedicularis verticillata	LOTUS Database	35616633
Plantago sempervirens	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
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Oxane
Monosaccharide
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
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	-2.7	ChemAxon
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.64 m³·mol⁻¹	ChemAxon
Polarizability	38.93 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

C00010595

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

15726439

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Herrera-Ruiz M, Lopez-Rodriguez R, Trejo-Tapia G, Dominguez-Mendoza BE, Gonzalez-Cortazar M, Tortoriello J, Zamilpa A: A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth. Molecules. 2015 Jul 21;20(7):13127-43. doi: 10.3390/molecules200713127. [PubMed:26197306 ]
Venditti A, Serrilli AM, Di Cecco M, Ciaschetti G, Andrisano T, Bianco A: Phytochemical analysis of Plantago sempervirens from Majella National Park. Nat Prod Res. 2012 Nov;26(21):2035-9. doi: 10.1080/14786419.2011.633520. Epub 2011 Nov 14. [PubMed:22081901 ]
Shahzadi T, Abbasi MA, Ur-Rehman A, Riaz T, Khan KM, Ashraf M, Afzal I, Akhtar MN, Ajaib M: Antioxidant and lipoxygenase inhibiting new iridoid glucosides from Caryopteris odorata. Nat Prod Res. 2013 Mar;27(4-5):302-13. doi: 10.1080/14786419.2012.668692. Epub 2012 Mar 16. [PubMed:22424117 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0283876)

MOL for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0283876 (methyl (1s,6s,7r)-6,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)