NP-MRD: Showing NP-Card for Syringaresinol (NP0137472)

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Record Information

Version

2.0

Created at

2022-05-30 16:53:27 UTC

Updated at

2024-09-03 04:21:25 UTC

NP-MRD ID

NP0137472

Natural Product DOI

https://doi.org/10.57994/2479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Syringaresinol

Description

Lirioresinol A, also known as S(8-8)S or syringaresinol, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Lirioresinol A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lirioresinol A has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make lirioresinol a a potential biomarker for the consumption of these foods. Syringaresinol is found in Aglaia odorata, Ailanthus altissima, Allium cepa, Annona cherimola, Annona montana, Antidesma membranaceum, Apollonias barbujana, Arabidopsis thaliana, Aralia bipinnata, Arcangelisia gusanlung, Artabotrys hexapetalus, Artemisia reptans, Asclepias curassavica, Aspidosperma excelsum, Bambusa emeiensis, Berberis koreana, Breynia vitis-idaea, Brucea javanica, Buddleja davidii, Bulbophyllum vaginatum, Bupleurum salicifolium, Caragana tibetica, Carduus tenuiflorus, Cassytha filiformis, Celastrus flagellaris, Centaurea arenaria, Chrysanthemum indicum, Cinnamomum aromaticum, Cinnamomum kotoense, Cinnamomum macrostemon, Cinnamomum reticulatum, Cinnamomum subavenium, Cinnamomum tenuifolium, Citrus medica, Citrus trifoliata, Cocculus orbiculatus, Colocasia esculenta, Daphne feddei, Daphne giraldii, Daphne mezereum, Dendrobium nobile, Dendrobium plicatile, Dioscorea spongiosa, Diospyros kaki, Dirca occidentalis, Dracaena draco, Eleutherococcus senticosus, Eleutherococcus sessiliflorus, Ephedra alata, Erythrina latissima, Euchresta formosana, Eucommia ulmoides, Euonymus alatus, Euterpe oleracea, Ficus septica, Firmiana simplex, Gentiana lutea, Gnetum montanum, Goniothalamus tapis, Hedyotis lawsoniae, Helianthus annuus, Helicteres angustifolia, Hernandia ovigera, Hibiscus cannabinus, Hibiscus syriacus, Hibiscus taiwanensis, Ipomoea nil, Leitneria floridana, Leptadenia arborea, Liriodendron tulipifera, Litsea hypophaea, Lycopus lucidus, Machilus thunbergii, Magnolia coco, Magnolia denudata, Magnolia figo, Magnolia kobus, Magnolia officinalis, Berberis repens, Magnolia sinica, Matricaria aurea, Magnolia alba, Magnolia compressa, Morinda citrifolia, Onopordum acaulon, Ormosia henryi, Peltostigma guatemalense, Peperomia heyneana, Phellodendron chinense, Picris rhagadioloides, Pittosporum illicioides, Platycarya strobilacea, Premna fulva, Rhaphidophora decursiva, Rinorea anguifera, Rubus chamaemorus, Saccharum officinarum, Santalum album, Saussurea medusa, Secale cereale, Selaginella doederleinii, Stellera chamaejasme, Strychnos spinosa, Styrax camporum, Syringa pubescens, Syringa vulgaris, Tamarix nilotica, Toddalia asiatica, Tripterygium wilfordii, Viburnum foetidum, Viscum album, Viscum coloratum, Vitis vinifera, Wikstroemia indica, Wisteria floribunda, Xanthium strumarium, Zanthoxylum ailanthoides, Zanthoxylum avicennae, Zanthoxylum nitidum, Zanthoxylum simulans and Zanthoxylum wutaiense. Syringaresinol was first documented in 2001 (PMID: 11152952). A lignan that is 7,9':7',9-Diepoxylignane substituted by hydroxy groups at positions 4 and 4' and methoxy groups at positions 3, 3', 5 and 5' respectively (PMID: 12081149) (PMID: 22170035) (PMID: 25415049) (PMID: 25479772).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309271714262D          

 30 33  0  0  0  0            999 V2000
    0.3392    3.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    2.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547    0.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0617    0.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236    1.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4848   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2452   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3342   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5272   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   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
  4  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  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    4.4007    0.6235    4.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083    0.3759    3.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    0.2939    1.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.4596    1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    0.3835    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022    0.5639   -0.0325 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1294    1.3888   -1.1059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295    0.9800   -1.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -0.2204   -1.0075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4313    0.0814    0.1668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8774    0.1194   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4059    0.2889   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7629    0.3160   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3042    0.4914   -2.9050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094    0.6505   -4.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5942    0.1629   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9556    0.1882   -0.7468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1049   -0.0138    0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9611   -0.1658    1.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4068   -0.3412    3.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393   -0.0329    0.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -0.9680    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -1.3611    0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6938   -0.7475   -0.3008 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7242    0.1359   -0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0745   -0.0283   -0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901   -0.2807   -1.5910 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5613   -0.3769   -2.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961    0.0464    0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509   -0.1230    0.9373 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738    1.4437    3.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0178    0.9201    5.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7954   -0.2629    4.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421    0.6511    2.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515    0.9877    0.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8224    1.7687   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240    0.6787   -2.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.9982   -1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1398    1.0633    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319    0.4064   -2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.0883   -3.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1363    0.3610   -4.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1622    1.6808   -4.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5908    0.0786    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2376   -0.5401    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396   -1.2488    3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242    0.5754    3.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   -0.1708    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6222   -1.1021    1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -2.4870    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -1.4319   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3839    0.0632   -1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -0.6012   -3.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061    0.6204   -3.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8005   -1.1869   -2.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2974   -0.0618    1.8868 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
  4  5  1  0
  5 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 24  1  0
 24 23  1  0
 23 22  1  0
 22 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 29  3  1  0
 24  6  1  0
 21 11  1  0
 10  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
 25 52  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 30 56  1  0
  6 35  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  6
 24 51  1  6
 23 49  1  0
 23 50  1  0
 10 39  1  1
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END


  Mrv1652309271714262D          

 30 33  0  0  0  0            999 V2000
    0.3392    3.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    2.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547    0.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0617    0.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236    1.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4848   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2452   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3342   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5272   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   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
  4  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  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3

> <INCHI_KEY>
KOWMJRJXZMEZLD-UHFFFAOYSA-N

> <FORMULA>
C22H26O8

> <MOLECULAR_WEIGHT>
418.437

> <EXACT_MASS>
418.162767808

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.995113664664714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.9624170159999994

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.60402888358133

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.001968892253409

> <JCHEM_PKA_STRONGEST_BASIC>
-3.741418411118898

> <JCHEM_POLAR_SURFACE_AREA>
95.84000000000002

> <JCHEM_REFRACTIVITY>
108.02659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
syringaresinol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-17         0                                  
HETATM    1  C   UNK     0       0.633   6.683   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.079   4.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.555   2.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.475   1.464   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.982   1.785   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.964   3.569   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.440   5.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.427   4.394   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.903   5.858   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -2.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.835  -1.246   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.912  -4.276   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.894  -6.061   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.924  -4.917   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.820  -7.710   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.314  -7.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   20                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)	ChEBI
S(8-8)S	ChEBI
(+)-Episyringaresinol	HMDB
Symplicosigenol	HMDB
Syringaresinol	HMDB
Syringa-resinol	HMDB
Syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomer	HMDB
Syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomer	HMDB

Chemical Formula

C₂₂H₂₆O₈

Average Mass

418.4370 Da

Monoisotopic Mass

418.16277 Da

IUPAC Name

4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

Traditional Name

syringaresinol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3

InChI Key

KOWMJRJXZMEZLD-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	hxkuang@hljucm.net	Not Available	Not Available	2024-05-11	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aglaia odorata	LOTUS Database	35616633
Ailanthus altissima	LOTUS Database	35616633
Allium cepa	LOTUS Database	35616633
Annona cherimola	LOTUS Database	35616633
Annona montana	LOTUS Database	35616633
Antidesma membranaceum	LOTUS Database	35616633
Apollonias barbujana	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Aralia bipinnata	LOTUS Database	35616633
Arcangelisia gusanlung	LOTUS Database	35616633
Artabotrys hexapetalus	LOTUS Database	35616633
Artemisia reptans	LOTUS Database	35616633
Asclepias curassavica	LOTUS Database	35616633
Aspidosperma excelsum	LOTUS Database	35616633
Bambusa emeiensis	LOTUS Database	35616633
Berberis koreana	LOTUS Database	35616633
Breynia vitis-idaea	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Buddleja davidii	LOTUS Database	35616633
Bulbophyllum vaginatum	LOTUS Database	35616633
Bupleurum salicifolium	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Carduus tenuiflorus	LOTUS Database	35616633
Cassytha filiformis	LOTUS Database	35616633
Celastrus flagellaris	LOTUS Database	35616633
Centaurea arenaria	LOTUS Database	35616633
Chrysanthemum indicum	LOTUS Database	35616633
Cinnamomum aromaticum	LOTUS Database	35616633
Cinnamomum kotoense	LOTUS Database	35616633
Cinnamomum macrostemon	LOTUS Database	35616633
Cinnamomum reticulatum	LOTUS Database	35616633
Cinnamomum subavenium	LOTUS Database	35616633
Cinnamomum tenuifolium	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus trifoliata	LOTUS Database	35616633
Cocculus orbiculatus	LOTUS Database	35616633
Colocasia esculenta	LOTUS Database	35616633
Daphne feddei	LOTUS Database	35616633
Daphne giraldii	LOTUS Database	35616633
Daphne mezereum	LOTUS Database	35616633
Datura metel		Not Available
Dendrobium nobile	LOTUS Database	35616633
Dendrobium plicatile	LOTUS Database	35616633
Dioscorea spongiosa	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Dirca occidentalis	LOTUS Database	35616633
Dracaena draco	LOTUS Database	35616633
Eleutherococcus senticosus	LOTUS Database	35616633
Eleutherococcus sessiliflorus	LOTUS Database	35616633
Ephedra alata	LOTUS Database	35616633
Erythrina latissima	LOTUS Database	35616633
Euchresta formosana	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Euonymus alatus	LOTUS Database	35616633
Euterpe oleracea	LOTUS Database	35616633
Ficus septica	LOTUS Database	35616633
Firmiana simplex	LOTUS Database	35616633
Gentiana lutea	LOTUS Database	35616633
Gnetum montanum	LOTUS Database	35616633
Goniothalamus tapis	LOTUS Database	35616633
Hedyotis lawsoniae	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helicteres angustifolia	LOTUS Database	35616633
Hernandia ovigera	LOTUS Database	35616633
Hibiscus cannabinus	LOTUS Database	35616633
Hibiscus syriacus	LOTUS Database	35616633
Hibiscus taiwanensis	LOTUS Database	35616633
Ipomoea nil	LOTUS Database	35616633
Leitneria floridana	LOTUS Database	35616633
Leptadenia arborea	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Litsea hypophaea	LOTUS Database	35616633
Lycopus lucidus	LOTUS Database	35616633
Machilus thunbergii	LOTUS Database	35616633
Magnolia coco	LOTUS Database	35616633
Magnolia denudata	LOTUS Database	35616633
Magnolia figo	LOTUS Database	35616633
Magnolia kobus	LOTUS Database	35616633
Magnolia officinalis	LOTUS Database	35616633
Mahonia repens	LOTUS Database	35616633
Manglietiastrum sinicum	LOTUS Database	35616633
Matricaria aurea	LOTUS Database	35616633
Michelia alba	LOTUS Database	35616633
Michelia compressa	LOTUS Database	35616633
Morinda citrifolia	LOTUS Database	35616633
Onopordum acaulon	LOTUS Database	35616633
Ormosia henryi	LOTUS Database	35616633
Peltostigma guatemalense	LOTUS Database	35616633
Peperomia heyneana	LOTUS Database	35616633
Phellodendron chinense	LOTUS Database	35616633
Picris rhagadioloides	LOTUS Database	35616633
Pittosporum illicioides	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Premna fulva	LOTUS Database	35616633
Rhaphidophora decursiva	LOTUS Database	35616633
Rinorea anguifera	LOTUS Database	35616633
Rubus chamaemorus	LOTUS Database	35616633
Saccharum officinarum	LOTUS Database	35616633
Santalum album	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Secale cereale	LOTUS Database	35616633
Selaginella doederleinii	LOTUS Database	35616633
Stellera chamaejasme	LOTUS Database	35616633
Strychnos spinosa	LOTUS Database	35616633
Styrax camporum	LOTUS Database	35616633
Syringa pubescens Turcz.	LOTUS Database	35616633
Syringa vulgaris	LOTUS Database	35616633
Tamarix nilotica	LOTUS Database	35616633
Toddalia asiatica	LOTUS Database	35616633
Tripterygium wilfordii	LOTUS Database	35616633
Viburnum foetidum	LOTUS Database	35616633
Viscum album	LOTUS Database	35616633
Viscum coloratum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Wikstroemia indica	LOTUS Database	35616633
Wisteria floribunda	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633
Zanthoxylum avicennae	LOTUS Database	35616633
Zanthoxylum nitidum	LOTUS Database	35616633
Zanthoxylum simulans	LOTUS Database	35616633
Zanthoxylum wutaiense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Furofuran
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lignan (CHEBI:49211 )

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	2.23	ALOGPS
logP	1.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.03 m³·mol⁻¹	ChemAxon
Polarizability	43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0038928

DrugBank ID

Not Available

Phenol Explorer Compound ID

598

FoodDB ID

FDB018395

KNApSAcK ID

Not Available

Chemspider ID

90423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100067

PDB ID

Not Available

ChEBI ID

49211

Good Scents ID

Not Available

References

General References

Sharp H, Thomas D, Currie F, Bright C, Latif Z, Sarker SD, Nash RJ: Pinoresinol and syringaresinol: two lignans from Avicennia germinans (Avicenniaceae). Biochem Syst Ecol. 2001 Mar;29(3):325-327. doi: 10.1016/s0305-1978(00)00050-8. [PubMed:11152952 ]
Chiba K, Yamazaki M, Umegaki E, Li MR, Xu ZW, Terada S, Taka M, Naoi N, Mohri T: Neuritogenesis of herbal (+)- and (-)-syringaresinols separated by chiral HPLC in PC12h and Neuro2a cells. Biol Pharm Bull. 2002 Jun;25(6):791-3. doi: 10.1248/bpb.25.791. [PubMed:12081149 ]
Chung BH, Kim S, Kim JD, Lee JJ, Baek YY, Jeoung D, Lee H, Choe J, Ha KS, Won MH, Kwon YG, Kim YM: Syringaresinol causes vasorelaxation by elevating nitric oxide production through the phosphorylation and dimerization of endothelial nitric oxide synthase. Exp Mol Med. 2012 Mar 31;44(3):191-201. doi: 10.3858/emm.2012.44.3.014. [PubMed:22170035 ]
Cho S, Cho M, Kim J, Kaeberlein M, Lee SJ, Suh Y: Syringaresinol protects against hypoxia/reoxygenation-induced cardiomyocytes injury and death by destabilization of HIF-1alpha in a FOXO3-dependent mechanism. Oncotarget. 2015 Jan 1;6(1):43-55. doi: 10.18632/oncotarget.2723. [PubMed:25415049 ]
Park HW, Cho SY, Kim HH, Yun BS, Kim JU, Lee SJ, Park J: Enantioselective induction of SIRT1 gene by syringaresinol from Panax ginseng berry and Acanthopanax senticosus Harms stem. Bioorg Med Chem Lett. 2015 Jan 15;25(2):307-9. doi: 10.1016/j.bmcl.2014.11.045. Epub 2014 Nov 22. [PubMed:25479772 ]
DOI: 10.1016/j.phytol.2022.04.008
PII: s1874390022000866

Showing NP-Card for Syringaresinol (NP0137472)

MOL for NP0137472 (Syringaresinol)

3D MOL for NP0137472 (Syringaresinol)

3D SDF for NP0137472 (Syringaresinol)

3D-SDF for NP0137472 (Syringaresinol)

PDB for NP0137472 (Syringaresinol)

3D PDB for NP0137472 (Syringaresinol)

SMILES for NP0137472 (Syringaresinol)

INCHI for NP0137472 (Syringaresinol)

Structure for NP0137472 (Syringaresinol)

3D Structure for NP0137472 (Syringaresinol)