NP-MRD: Showing NP-Card for loganic acid (NP0030978)

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Record Information

Version

1.0

Created at

2021-06-19 22:11:33 UTC

Updated at

2021-08-20 00:00:21 UTC

NP-MRD ID

NP0030978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

loganic acid

Provided By

JEOL Database JEOL Logo

Description

Loganic acid, also known as loganate, 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. loganic acid is found in Alangium platanifolium, Castilleja integra, Cistanche tubulosa , Desfontainia spinosa, Dipsacus asperoides, Erinus alpinus, Fagraea ceilanica, Fontanesia phillyreoides, Gentiana dahurica, Gentiana olivieri, Gentiana pedicellata, Gentiana septemfida, Gentiana thunbergii, Gentiana tibetica, Gmelina philippensis , Guettarda platypoda, Guettarda speciosa, Ixanthus viscosus, Ligustrum ovalifolium Hassk., Loasa pinnatifida, Lonicera caerulea, Lonicera periclymenum, Patrinia scabra, Pedicularis bracteosa, Pedicularis crenulata, Pedicularis groenlandica, Pedicularis longiflora, Pedicularis procera, Pedicularis racemosa, Pedicularis torta, Penstemon barbatus, Phillyrea latifolia L. , Picconia excelsa, Plantago alpina, Plantago altissima , Plantago arborescens, Plantago atrata, Plantago hookeriana, Plantago lundborgii, Plantago ovata , Plantago raoulii, Plantago stauntonii, Plantago webbii, Pterocephalus perennis, Radix gentianae, Rauvolfia grandiflora, Rauwolfia serpentina, Scrophularia canina , Scutellaria albida subsp.albida, Sertia mussotii, Strychnos cocculoides, Strychnos nux-vomica, Triaenophora rupestris, Veronica beccabunga , Veronica derwentiana, Veronica perfoliata and Vinca major. It was first documented in 2021 (PMID: 34214834). Based on a literature review a significant number of articles have been published on Loganic acid (PMID: 33766757) (PMID: 34112794) (PMID: 33933979) (PMID: 33532692).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100113D          

 50 52  0  0  0  0            999 V2000
    2.5717   -0.0635   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    1.1668   -1.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5352    2.0205   -2.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0632    1.2054   -3.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    2.9269   -2.8475 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1115    2.1551   -2.6966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059    2.9387   -1.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    4.2485   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828    5.0343   -1.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    4.5117   -3.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    2.4890   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.2686   -0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323    0.2880   -1.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6816   -0.1737   -1.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.9782   -1.2744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0666   -2.2538   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -3.1069   -0.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2637   -4.4071    0.0692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0929   -4.1066    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387   -3.3779   -1.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2012   -4.1564   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8767   -2.0517   -1.5534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9570   -2.3179   -2.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8438   -1.1404   -2.2093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4607    0.1237   -2.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4948    0.8282   -1.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5489    0.2259   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -0.5960   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369   -0.7676   -1.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    1.7845   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    2.5860   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.7877   -3.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    3.8668   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.1715   -3.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    1.9276   -3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    5.3868   -3.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722    3.0516   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5574   -0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -0.4645   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.6148    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909   -5.0835    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -4.9261   -0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215   -3.4188    0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -3.9445   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0120   -4.1292   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345   -1.5574   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2091   -1.4423   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324   -1.5618   -3.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7295    0.7112   -2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    0.0852   -2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 13  1  0  0  0  0
 26 50  1  6  0  0  0
 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 11  1  0  0  0  0
  3  4  1  0  0  0  0
  6  5  1  0  0  0  0
 13 14  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 26  1  0  0  0  0
 11  7  2  0  0  0  0
  7  8  1  0  0  0  0
 26  6  1  0  0  0  0
  8 10  1  0  0  0  0
  8  9  2  0  0  0  0
  6  7  1  0  0  0  0
 15 24  1  0  0  0  0
 24 22  1  0  0  0  0
 22 20  1  0  0  0  0
 20 17  1  0  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
  6 35  1  6  0  0  0
 18 19  1  0  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 13 38  1  1  0  0  0
 11 37  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  3 31  1  1  0  0  0
  2 30  1  1  0  0  0
 10 36  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 32  1  0  0  0  0
 15 39  1  1  0  0  0
 20 44  1  6  0  0  0
 21 45  1  0  0  0  0
 22 46  1  1  0  0  0
 23 47  1  0  0  0  0
 24 48  1  6  0  0  0
 25 49  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 17 40  1  1  0  0  0
 19 43  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    2.5717   -0.0635   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    1.1668   -1.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5352    2.0205   -2.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0632    1.2054   -3.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    2.9269   -2.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    2.1551   -2.6966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059    2.9387   -1.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    4.2485   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828    5.0343   -1.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    4.5117   -3.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    2.4890   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.2686   -0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323    0.2880   -1.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6816   -0.1737   -1.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.9782   -1.2744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0666   -2.2538   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -3.1069   -0.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2637   -4.4071    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0929   -4.1066    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387   -3.3779   -1.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2012   -4.1564   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8767   -2.0517   -1.5534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9570   -2.3179   -2.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8438   -1.1404   -2.2093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4607    0.1237   -2.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4948    0.8282   -1.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5489    0.2259   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -0.5960   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369   -0.7676   -1.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    1.7845   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    2.5860   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.7877   -3.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    3.8668   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.1715   -3.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    1.9276   -3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    5.3868   -3.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722    3.0516   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5574   -0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -0.4645   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8909   -5.0835    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9628   -3.9445   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0120   -4.1292   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345   -1.5574   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2091   -1.4423   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324   -1.5618   -3.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7295    0.7112   -2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    0.0852   -2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 13  1  0
 26 50  1  6
 13 12  1  0
  2  1  1  0
 12 11  1  0
  3  4  1  0
  6  5  1  0
 13 14  1  0
  5  3  1  0
  3  2  1  0
  2 26  1  0
 11  7  2  0
  7  8  1  0
 26  6  1  0
  8 10  1  0
  8  9  2  0
  6  7  1  0
 15 24  1  0
 24 22  1  0
 22 20  1  0
 20 17  1  0
 17 16  1  0
 16 15  1  0
 20 21  1  0
 22 23  1  0
 24 25  1  0
  6 35  1  6
 18 19  1  0
 17 18  1  0
 15 14  1  0
 13 38  1  1
 11 37  1  0
  5 33  1  0
  5 34  1  0
  3 31  1  1
  2 30  1  1
 10 36  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 32  1  0
 15 39  1  1
 20 44  1  6
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 22 46  1  1
 23 47  1  0
 24 48  1  6
 25 49  1  0
 18 41  1  0
 18 42  1  0
 17 40  1  1
 19 43  1  0
M  END


  Mrv1652306202100113D          

 50 52  0  0  0  0            999 V2000
    2.5717   -0.0635   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    1.1668   -1.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5352    2.0205   -2.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0632    1.2054   -3.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    2.9269   -2.8475 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1115    2.1551   -2.6966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059    2.9387   -1.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    4.2485   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828    5.0343   -1.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    4.5117   -3.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    2.4890   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.2686   -0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323    0.2880   -1.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6816   -0.1737   -1.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.9782   -1.2744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0666   -2.2538   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -3.1069   -0.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2637   -4.4071    0.0692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0929   -4.1066    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387   -3.3779   -1.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2012   -4.1564   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8767   -2.0517   -1.5534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9570   -2.3179   -2.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8438   -1.1404   -2.2093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4607    0.1237   -2.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4948    0.8282   -1.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5489    0.2259   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -0.5960   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369   -0.7676   -1.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    1.7845   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    2.5860   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.7877   -3.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    3.8668   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.1715   -3.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    1.9276   -3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    5.3868   -3.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722    3.0516   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5574   -0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -0.4645   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.6148    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909   -5.0835    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -4.9261   -0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215   -3.4188    0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -3.9445   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0120   -4.1292   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345   -1.5574   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2091   -1.4423   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324   -1.5618   -3.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7295    0.7112   -2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    0.0852   -2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 13  1  0  0  0  0
 26 50  1  6  0  0  0
 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 11  1  0  0  0  0
  3  4  1  0  0  0  0
  6  5  1  0  0  0  0
 13 14  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 26  1  0  0  0  0
 11  7  2  0  0  0  0
  7  8  1  0  0  0  0
 26  6  1  0  0  0  0
  8 10  1  0  0  0  0
  8  9  2  0  0  0  0
  6  7  1  0  0  0  0
 15 24  1  0  0  0  0
 24 22  1  0  0  0  0
 22 20  1  0  0  0  0
 20 17  1  0  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
  6 35  1  6  0  0  0
 18 19  1  0  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 13 38  1  1  0  0  0
 11 37  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  3 31  1  1  0  0  0
  2 30  1  1  0  0  0
 10 36  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 32  1  0  0  0  0
 15 39  1  1  0  0  0
 20 44  1  6  0  0  0
 21 45  1  0  0  0  0
 22 46  1  1  0  0  0
 23 47  1  0  0  0  0
 24 48  1  6  0  0  0
 25 49  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 17 40  1  1  0  0  0
 19 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@@]2([H])[C@]1([H])C([H])([H])[C@]([H])(O[H])[C@]2([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1

> <INCHI_KEY>
JNNGEAWILNVFFD-CDJYTOATSA-N

> <FORMULA>
C16H24O10

> <MOLECULAR_WEIGHT>
376.358

> <EXACT_MASS>
376.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.30430761209824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,6S,7R,7aS)-6-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-carboxylic acid

> <ALOGPS_LOGP>
-2.01

> <JCHEM_LOGP>
-2.216372853666667

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.206193523365306

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.257309327635798

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8340462513225235

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
82.70530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
loganic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    2.5717   -0.0635   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    1.1668   -1.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5352    2.0205   -2.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0632    1.2054   -3.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    2.9269   -2.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    2.1551   -2.6966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059    2.9387   -1.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    4.2485   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828    5.0343   -1.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    4.5117   -3.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    2.4890   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.2686   -0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323    0.2880   -1.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6816   -0.1737   -1.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.9782   -1.2744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0666   -2.2538   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -3.1069   -0.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2637   -4.4071    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0929   -4.1066    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387   -3.3779   -1.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2012   -4.1564   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8767   -2.0517   -1.5534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9570   -2.3179   -2.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8438   -1.1404   -2.2093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4607    0.1237   -2.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4948    0.8282   -1.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5489    0.2259   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -0.5960   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369   -0.7676   -1.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    1.7845   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    2.5860   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.7877   -3.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    3.8668   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.1715   -3.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    1.9276   -3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    5.3868   -3.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722    3.0516   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5574   -0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -0.4645   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.6148    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909   -5.0835    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -4.9261   -0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215   -3.4188    0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -3.9445   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0120   -4.1292   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345   -1.5574   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2091   -1.4423   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324   -1.5618   -3.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7295    0.7112   -2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    0.0852   -2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 13  1  0
 26 50  1  6
 13 12  1  0
  2  1  1  0
 12 11  1  0
  3  4  1  0
  6  5  1  0
 13 14  1  0
  5  3  1  0
  3  2  1  0
  2 26  1  0
 11  7  2  0
  7  8  1  0
 26  6  1  0
  8 10  1  0
  8  9  2  0
  6  7  1  0
 15 24  1  0
 24 22  1  0
 22 20  1  0
 20 17  1  0
 17 16  1  0
 16 15  1  0
 20 21  1  0
 22 23  1  0
 24 25  1  0
  6 35  1  6
 18 19  1  0
 17 18  1  0
 15 14  1  0
 13 38  1  1
 11 37  1  0
  5 33  1  0
  5 34  1  0
  3 31  1  1
  2 30  1  1
 10 36  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 32  1  0
 15 39  1  1
 20 44  1  6
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  6
 25 49  1  0
 18 41  1  0
 18 42  1  0
 17 40  1  1
 19 43  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.572  -0.064  -0.796  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.794   1.167  -1.247  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.535   2.021  -2.277  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.063   1.205  -3.317  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.447   2.927  -2.848  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.112   2.155  -2.697  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.906   2.939  -1.910  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.397   4.248  -2.378  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.083   5.034  -1.751  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.016   4.512  -3.638  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.399   2.489  -0.747  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.121   1.269  -0.188  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.632   0.288  -1.116  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.682  -0.174  -1.977  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.632  -0.978  -1.274  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.067  -2.254  -0.972  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.998  -3.107  -0.274  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.264  -4.407   0.069  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.093  -4.107   0.833  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.239  -3.378  -1.135  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.201  -4.156  -0.423  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.877  -2.052  -1.553  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.957  -2.318  -2.462  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.844  -1.140  -2.209  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.461   0.124  -2.500  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.495   0.828  -1.998  0.00  0.00           C+0
HETATM   27  H   UNK     0       3.549   0.226  -0.396  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.034  -0.596  -0.006  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.737  -0.768  -1.618  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.574   1.785  -0.366  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.358   2.586  -1.829  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.546   1.788  -3.930  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.429   3.867  -2.283  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.631   3.172  -3.900  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.309   1.928  -3.685  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.417   5.387  -3.824  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.072   3.052  -0.109  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.255  -0.557  -0.530  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.936  -0.465  -0.353  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.273  -2.615   0.669  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.891  -5.083   0.657  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.934  -4.926  -0.837  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.622  -3.419   0.326  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.963  -3.945  -2.033  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.012  -4.129  -0.972  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.335  -1.557  -0.687  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.209  -1.442  -2.821  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.532  -1.562  -3.173  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.729   0.711  -2.778  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.710   0.085  -2.780  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   26   30                                             
CONECT    3    4    5    2   31                                             
CONECT    4    3   32                                                       
CONECT    5    6    3   33   34                                             
CONECT    6    5   26    7   35                                             
CONECT    7   11    8    6                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   36                                                       
CONECT   11   12    7   37                                                  
CONECT   12   13   11                                                       
CONECT   13   26   12   14   38                                             
CONECT   14   13   15                                                       
CONECT   15   24   16   14   39                                             
CONECT   16   17   15                                                       
CONECT   17   20   16   18   40                                             
CONECT   18   19   17   41   42                                             
CONECT   19   18   43                                                       
CONECT   20   22   17   21   44                                             
CONECT   21   20   45                                                       
CONECT   22   24   20   23   46                                             
CONECT   23   22   47                                                       
CONECT   24   15   22   25   48                                             
CONECT   25   24   49                                                       
CONECT   26   13   50    2    6                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   13                                                            
CONECT   39   15                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    2.5717   -0.0635   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    1.1668   -1.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5352    2.0205   -2.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0632    1.2054   -3.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    2.9269   -2.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    2.1551   -2.6966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059    2.9387   -1.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    4.2485   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828    5.0343   -1.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    4.5117   -3.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    2.4890   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.2686   -0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323    0.2880   -1.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6816   -0.1737   -1.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.9782   -1.2744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0666   -2.2538   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -3.1069   -0.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2637   -4.4071    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0929   -4.1066    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387   -3.3779   -1.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2012   -4.1564   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8767   -2.0517   -1.5534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9570   -2.3179   -2.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8438   -1.1404   -2.2093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4607    0.1237   -2.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4948    0.8282   -1.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5489    0.2259   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -0.5960   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369   -0.7676   -1.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    1.7845   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    2.5860   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.7877   -3.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    3.8668   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.1715   -3.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    1.9276   -3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    5.3868   -3.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722    3.0516   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.5574   -0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -0.4645   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.6148    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909   -5.0835    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -4.9261   -0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215   -3.4188    0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628   -3.9445   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0120   -4.1292   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345   -1.5574   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2091   -1.4423   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324   -1.5618   -3.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7295    0.7112   -2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    0.0852   -2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 13  1  0
 26 50  1  6
 13 12  1  0
  2  1  1  0
 12 11  1  0
  3  4  1  0
  6  5  1  0
 13 14  1  0
  5  3  1  0
  3  2  1  0
  2 26  1  0
 11  7  2  0
  7  8  1  0
 26  6  1  0
  8 10  1  0
  8  9  2  0
  6  7  1  0
 15 24  1  0
 24 22  1  0
 22 20  1  0
 20 17  1  0
 17 16  1  0
 16 15  1  0
 20 21  1  0
 22 23  1  0
 24 25  1  0
  6 35  1  6
 18 19  1  0
 17 18  1  0
 15 14  1  0
 13 38  1  1
 11 37  1  0
  5 33  1  0
  5 34  1  0
  3 31  1  1
  2 30  1  1
 10 36  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 32  1  0
 15 39  1  1
 20 44  1  6
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  6
 25 49  1  0
 18 41  1  0
 18 42  1  0
 17 40  1  1
 19 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
Loganate	Generator
Loganic acid	KEGG
8-Epiloganic acid	MeSH
Loganin acid	PhytoBank

Chemical Formula

C₁₆H₂₄O₁₀

Average Mass

376.3580 Da

Monoisotopic Mass

376.13695 Da

IUPAC Name

(1S,4aS,6S,7R,7aS)-6-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-carboxylic acid

Traditional Name

loganic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@@]2([H])[C@]1([H])C([H])([H])[C@]([H])(O[H])[C@]2([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1

InChI Key

JNNGEAWILNVFFD-CDJYTOATSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alangium lamarckii	KNApSAcK Database	22123792
Alangium platanifolium	LOTUS Database	35616633
Castilleja integra	Plant	KNApSAcK
Catharanthus roseus	KNApSAcK Database	22123792
Centaurium erythraea	KNApSAcK Database	22123792
Cistanche tubulosa	Plant	KNApSAcK
Cornus officinalis	KNApSAcK Database	22123792
Desfontainia spinosa	LOTUS Database	35616633
Dipsacus asperoides	LOTUS Database	35616633
Erinus alpinus	Plant	KNApSAcK
Fagraea ceilanica	LOTUS Database	35616633
Fontanesia fortunei Carr.	KNApSAcK Database	22123792
Fontanesia philliraeoides	LOTUS Database	35616633
Fontanesia phillyreoides Labill.	KNApSAcK Database	22123792
Frasera caroliniensis	KNApSAcK Database	22123792
Gentiana algida	KNApSAcK Database	22123792
Gentiana crassicaulis	KNApSAcK Database	22123792
Gentiana dahurica	LOTUS Database	35616633
Gentiana decumbers	KNApSAcK Database	22123792
Gentiana lawrencei	KNApSAcK Database	22123792
Gentiana loureirii	KNApSAcK Database	22123792
Gentiana lutea	KNApSAcK Database	22123792
Gentiana macrophylla	KNApSAcK Database	22123792
Gentiana manshurica	KNApSAcK Database	22123792
Gentiana officinalis	KNApSAcK Database	22123792
Gentiana olivieri	LOTUS Database	35616633
Gentiana pedicellata	LOTUS Database	35616633
Gentiana rhodantha	KNApSAcK Database	22123792
Gentiana rigescens	KNApSAcK Database	22123792
Gentiana scabra	KNApSAcK Database	22123792
Gentiana septemfida	LOTUS Database	35616633
Gentiana straminea	KNApSAcK Database	22123792
Gentiana thunbergii	LOTUS Database	35616633
Gentiana tibetica	LOTUS Database	35616633
Gentiana triflora	KNApSAcK Database	22123792
Gmelina philippensis	Plant	KNApSAcK
Guettarda platypoda	LOTUS Database	35616633
Guettarda speciosa	LOTUS Database	35616633
Ixanthus viscosus	LOTUS Database	35616633
Ligustrum ovalifolium	Plant	KNApSAcK
Lippia graveolens	KNApSAcK Database	22123792
Loasa pinnatifida	LOTUS Database	35616633
Lonicera caerulea	LOTUS Database	35616633
Lonicera japonica	KNApSAcK Database	22123792
Lonicera periclymenum	LOTUS Database	35616633
Ophiorrhiza liukiuensis	KNApSAcK Database	22123792
Osmanthus austrocaledonicus (Vieill.) Knobl.	KNApSAcK Database	22123792
Patrinia scabra	LOTUS Database	35616633
Pedicularis bracteosa	Plant	KNApSAcK
Pedicularis crenulata	Plant	KNApSAcK
Pedicularis groenlandica	Plant	KNApSAcK
Pedicularis longiflora	LOTUS Database	35616633
Pedicularis procera	Plant	KNApSAcK
Pedicularis racemosa	Plant	KNApSAcK
Pedicularis torta	LOTUS Database	35616633
Penstemon barbatus	LOTUS Database	35616633
Phillyrea latifolia	Plant	KNApSAcK
Picconia excelsa	LOTUS Database	35616633
Picconia excelsa (Aiton) DC.	KNApSAcK Database	22123792
Plantago alpina	Plant	KNApSAcK
Plantago altissima	Plant	KNApSAcK
Plantago arborescens	Plant	KNApSAcK
Plantago atrata	Plant	KNApSAcK
Plantago hookeriana	Plant	KNApSAcK
Plantago lundborgii	Plant	KNApSAcK
Plantago ovata	Plant	KNApSAcK
Plantago raoulii	Plant	KNApSAcK
Plantago stauntonii	Plant	KNApSAcK
Plantago webbii	Plant	KNApSAcK
Pterocephalus perennis	LOTUS Database	35616633
Radix gentianae	-	KNApSAcK
Rauvolfia grandiflora	LOTUS Database	35616633
Rauvolfia serpentina	Plant	KNApSAcK
Rauwolfia serpentina	KNApSAcK Database	22123792
Rehmannia glutinosa	KNApSAcK Database	22123792
Scrophularia canina	Plant	KNApSAcK
Scutellaria albida subsp.albida	Plant	KNApSAcK
Sertia mussotii	-	KNApSAcK
Sinoadina racemosa	KNApSAcK Database	22123792
Strychnos axillaris	KNApSAcK Database	22123792
Strychnos cocculoides	LOTUS Database	35616633
Strychnos lucida	KNApSAcK Database	22123792
Strychnos nux-vomica	KNApSAcK Database	22123792
Strychnos nux-vomica L.	JEOL database	Zhang, X., et al, Phytochemistry 64, 1341 (2003)
Swertia carolinensis	KNApSAcK Database	22123792
Swertia davidii	KNApSAcK Database	22123792
Triaenophora rupestris	Plant	KNApSAcK
Tripterospermum japonicum	KNApSAcK Database	22123792
Veronica beccabunga	Plant	KNApSAcK
Veronica derwentiana	Plant	KNApSAcK
Veronica perfoliata	Plant	KNApSAcK
Vinca major	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
Secondary alcohol
Polyol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:30632 )
cyclopentapyran (CHEBI:30632 )
glucoside (CHEBI:30632 )
Iridoids (C01512 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	646.26 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.411 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-2.2	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-2.8	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	4	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	36.3 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loganic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

30632

Good Scents ID

rw1509501

References

General References

Zhou D, Lv D, Zhang H, Cheng T, Wang H, Lin P, Shi S, Chen S, Shen J: Quantitative analysis of the profiles of twelve major compounds in Gentiana straminea Maxim. Roots by LC-MS/MS in an extensive germplasm survey in the Qinghai-Tibetan plateau. J Ethnopharmacol. 2021 Mar 23;280:114068. doi: 10.1016/j.jep.2021.114068. [PubMed:33766757 ]
Xue Z, Xu L, Shang Z, Shi X, Ye M, Qiao X: Discovery of minor quality evaluation marker compounds for Chinese patent medicine products using a two-leveled metabolomics strategy. J Chromatogr A. 2021 Aug 30;1652:462354. doi: 10.1016/j.chroma.2021.462354. Epub 2021 Jun 20. [PubMed:34214834 ]
Kang M, Fu R, Zhang P, Lou S, Yang X, Chen Y, Ma T, Zhang Y, Xi Z, Liu J: A chromosome-level Camptotheca acuminata genome assembly provides insights into the evolutionary origin of camptothecin biosynthesis. Nat Commun. 2021 Jun 10;12(1):3531. doi: 10.1038/s41467-021-23872-9. [PubMed:34112794 ]
Spychaj R, Kucharska AZ, Szumny A, Przybylska D, Pejcz E, Piorecki N: Potential valorization of Cornelian cherry (Cornus mas L.) stones: Roasting and extraction of bioactive and volatile compounds. Food Chem. 2021 Oct 1;358:129802. doi: 10.1016/j.foodchem.2021.129802. Epub 2021 Apr 20. [PubMed:33933979 ]
Singh SK, Patra B, Paul P, Liu Y, Pattanaik S, Yuan L: BHLH IRIDOID SYNTHESIS 3 is a member of a bHLH gene cluster regulating terpenoid indole alkaloid biosynthesis in Catharanthus roseus. Plant Direct. 2021 Jan 25;5(1):e00305. doi: 10.1002/pld3.305. eCollection 2021 Jan. [PubMed:33532692 ]
Zhang, X., et al. (2003). Zhang, X., et al, Phytochemistry 64, 1341 (2003) . Phytochem..

Showing NP-Card for loganic acid (NP0030978)

MOL for NP0030978 (loganic acid)

3D MOL for NP0030978 (loganic acid)

3D SDF for NP0030978 (loganic acid)

3D-SDF for NP0030978 (loganic acid)

PDB for NP0030978 (loganic acid)

3D PDB for NP0030978 (loganic acid)

SMILES for NP0030978 (loganic acid)

INCHI for NP0030978 (loganic acid)

Structure for NP0030978 (loganic acid)

3D Structure for NP0030978 (loganic acid)