NP-MRD: Showing NP-Card for methyl (1s,4as,7s,7as)-7-hydroxy-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 (NP0320589)

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Record Information

Version

2.0

Created at

2022-09-11 22:19:26 UTC

Updated at

2022-09-11 22:19:27 UTC

NP-MRD ID

NP0320589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4as,7s,7as)-7-hydroxy-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

Mussaenoside 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,4as,7s,7as)-7-hydroxy-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 Aloysia citrodora, Aragoa cundinamarcensis, Avicennia marina, Bartsia alpina, Brandisia hancei, Castilleja affinis, Castilleja densiflora, Castilleja foliolosa, Castilleja miniata, Cordylanthus wrightii, Craniotome furcata, Dioecrescis erythroclada, Dodartia orientalis, Eccremocarpus scaber, Leonotis nepetifolia, Mackaya bella, Melampyrum arvense, Mussaenda pubescens, Pedicularis artselaeri, Pedicularis kansuensis, Pedicularis longiflora, Pedicularis muscicola, Pedicularis palustris, Pedicularis procera, Pedicularis rex, Pedicularis semitorta, Penstemon acuminatus, Penstemon barbatus, Rhinanthus angustifolius, Rothmannia globosa, Scyphiphora hydrophyllacea, Tarenna gracilipes, Veronica anagallis-aquatica, Veronica bellidioides, Veronica officinalis and Veronica pulvinaris. methyl (1s,4as,7s,7as)-7-hydroxy-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 2017 (PMID: 28507520). Based on a literature review a small amount of articles have been published on Mussaenoside (PMID: 32146842) (PMID: 36006221) (PMID: 35983769) (PMID: 30292367).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122200192D          

 27 29  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  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    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  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  6  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
   -6.9172    1.5227    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5734    1.0311    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169    1.8928    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450    3.1200    0.6652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1436    1.4488    0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2134    2.3377    0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217    1.9135    1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902    0.6488    0.4542 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8049    0.5336    0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    0.4685   -0.1477 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3102   -0.7905   -0.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -0.7892   -0.7166 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0744   -2.1823   -0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944   -2.8661    0.2388 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.1577    0.3165 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8187   -0.2857   -0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605    1.2727    0.4693 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1223    1.5952    1.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.5871   -0.1310 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9391    2.0473   -1.4337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -0.3496    1.0355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8339    0.0359    0.4595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6459   -0.3647   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775   -1.4541   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725   -1.7244    0.4594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2231   -2.5544    0.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -2.3847    0.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4857    1.3533    1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3763    0.9822   -0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8624    2.5991   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.3948    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390    0.6575   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1651    0.5207   -1.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.2091   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1272   -2.0543   -1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -2.7343   -1.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -2.5164    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2852   -0.6964    1.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2879    0.5286    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8710    1.8925   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323    2.2964    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390    2.4835    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.0706   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016   -0.3273    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5885   -0.6530    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    0.4780   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6301   -0.7728   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306   -2.3743   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768   -1.1686   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4943   -2.1110    1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826   -2.7496   -0.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5346   -3.5448    1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506   -2.8975    0.1324 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
 25 26  1  0
 25 27  1  1
 22  5  1  0
 19 10  1  0
 25 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  8 32  1  6
 10 33  1  6
 12 34  1  6
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  1
 16 39  1  0
 17 40  1  6
 18 41  1  0
 19 42  1  1
 20 43  1  0
 21 44  1  1
 22 45  1  1
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END


  Mrv1652309122200192D          

 27 29  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  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    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  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  6  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0320589

> <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)[C@H]2[C@@H]1CC[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O10/c1-17(23)4-3-7-8(14(22)24-2)6-25-15(10(7)17)27-16-13(21)12(20)11(19)9(5-18)26-16/h6-7,9-13,15-16,18-21,23H,3-5H2,1-2H3/t7-,9-,10-,11-,12+,13-,15+,16+,17+/m1/s1

> <INCHI_KEY>
XBGJTRDIWPEIMG-DUMNYRKASA-N

> <FORMULA>
C17H26O10

> <MOLECULAR_WEIGHT>
390.385

> <EXACT_MASS>
390.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.253114918655186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,7S,7aS)-7-hydroxy-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>
-1.6604624713333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.183867527427157

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20531093251842

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9699441284147214

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
87.2802

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,7S,7aS)-7-hydroxy-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                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   27  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   25                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆O₁₀

Average Mass

390.3850 Da

Monoisotopic Mass

390.15260 Da

IUPAC Name

methyl (1S,4aS,7S,7aS)-7-hydroxy-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,4aS,7S,7aS)-7-hydroxy-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)[C@H]2[C@@H]1CC[C@]2(C)O

InChI Identifier

InChI=1S/C17H26O10/c1-17(23)4-3-7-8(14(22)24-2)6-25-15(10(7)17)27-16-13(21)12(20)11(19)9(5-18)26-16/h6-7,9-13,15-16,18-21,23H,3-5H2,1-2H3/t7-,9-,10-,11-,12+,13-,15+,16+,17+/m1/s1

InChI Key

XBGJTRDIWPEIMG-DUMNYRKASA-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
Aloysia citrodora	LOTUS Database	35616633
Aragoa cundinamarcensis	LOTUS Database	35616633
Avicennia marina	LOTUS Database	35616633
Bartsia alpina	LOTUS Database	35616633
Brandisia hancei	LOTUS Database	35616633
Castilleja affinis	LOTUS Database	35616633
Castilleja densiflora	LOTUS Database	35616633
Castilleja foliolosa	LOTUS Database	35616633
Castilleja miniata	LOTUS Database	35616633
Cordylanthus wrightii	LOTUS Database	35616633
Craniotome furcata	LOTUS Database	35616633
Dioecrescis erythroclada	LOTUS Database	35616633
Dodartia orientalis	LOTUS Database	35616633
Eccremocarpus scaber	LOTUS Database	35616633
Leonotis nepetifolia	LOTUS Database	35616633
Mackaya bella	LOTUS Database	35616633
Melampyrum arvense	LOTUS Database	35616633
Mussaenda pubescens	LOTUS Database	35616633
Pedicularis artselaeri	LOTUS Database	35616633
Pedicularis kansuensis	LOTUS Database	35616633
Pedicularis longiflora	LOTUS Database	35616633
Pedicularis muscicola	LOTUS Database	35616633
Pedicularis palustris	LOTUS Database	35616633
Pedicularis procera	LOTUS Database	35616633
Pedicularis rex	LOTUS Database	35616633
Pedicularis semitorta	LOTUS Database	35616633
Penstemon acuminatus	LOTUS Database	35616633
Penstemon barbatus	LOTUS Database	35616633
Rhinanthus angustifolius	LOTUS Database	35616633
Rothmannia globosa	LOTUS Database	35616633
Scyphiphora hydrophyllacea	LOTUS Database	35616633
Tarenna gracilipes	LOTUS Database	35616633
Veronica anagallis-aquatica	LOTUS Database	35616633
Veronica bellidioides	LOTUS Database	35616633
Veronica officinalis	LOTUS Database	35616633
Veronica pulvinaris	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
Cyclic alcohol
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Methyl ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Polyol
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
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	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.28 m³·mol⁻¹	ChemAxon
Polarizability	38.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00010630

Chemspider ID

158664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182423

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thu VK, Bach NX, Dung CT, Cuong NT, Quang TH, Kim YC, Oh H, Kiem PV: Iridoids and cycloartane saponins from mussaenda pilosissima valeton and their inhibitory NO production in BV2 cells. Nat Prod Res. 2020 Mar 9:1-7. doi: 10.1080/14786419.2020.1737059. [PubMed:32146842 ]
Soriano G, Siciliano A, Fernandez-Aparicio M, Cala Peralta A, Masi M, Moreno-Robles A, Guida M, Cimmino A: Iridoid Glycosides Isolated from Bellardia trixago Identified as Inhibitors of Orobanche cumana Radicle Growth. Toxins (Basel). 2022 Aug 17;14(8):559. doi: 10.3390/toxins14080559. [PubMed:36006221 ]
Amin A, Tuenter E, Foubert K, Iqbal J, Cos P, Maes L, Exarchou V, Apers S, Pieters L: In Vitro and In Silico Antidiabetic and Antimicrobial Evaluation of Constituents from Kickxia ramosissima (Nanorrhinum ramosissimum). Front Pharmacol. 2017 May 1;8:232. doi: 10.3389/fphar.2017.00232. eCollection 2017. [PubMed:28507520 ]
Ranjana, Binwal M, Verma AK, Bawankule DU, Tiwari N, Shanker K: Stimulation of glucose uptake by glycosides from Alectra parasitica subsp. chitrakutensis (M.A. Rau) K.K. Khanna & An. Kumar: An in-vitro study of TNF-alpha induced insulin resistance in L6 myoblasts. Nat Prod Res. 2023 Jun;37(12):2024-2030. doi: 10.1080/14786419.2022.2112957. Epub 2022 Aug 19. [PubMed:35983769 ]
Gomes AF, Almeida MP, Leite MF, Schwaiger S, Stuppner H, Halabalaki M, Amaral JG, David JM: Seasonal variation in the chemical composition of two chemotypes of Lippia alba. Food Chem. 2019 Feb 1;273:186-193. doi: 10.1016/j.foodchem.2017.11.089. Epub 2017 Nov 23. [PubMed:30292367 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,4as,7s,7as)-7-hydroxy-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 (NP0320589)

MOL for NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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 NP0320589 (methyl (1s,4as,7s,7as)-7-hydroxy-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)