NP-MRD: Showing NP-Card for Acanthoside B (NP0137620)

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Record Information

Version

2.0

Created at

2022-05-30 16:57:57 UTC

Updated at

2022-05-30 16:57:57 UTC

NP-MRD ID

NP0137620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acanthoside B

Description

(+)-Syringaresinol beta-D-glucoside, also known as acanthoside b, belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. Acanthoside B is found in Acanthus ilicifolius, Acer saccharum, Apis cerana, Baccharis dracunculifolia, Beaumontia grandiflora, Cananga odorata, Casearia sylvestris, Cistanche salsa, Cistanche tubulosa, Dalbergia sissoo, Daphne feddei, Dendrobium moniliforme, Dendrobium nobile, Desfontainia spinosa, Eleutherococcus senticosus, Epimedium grandiflorum, Eucommia ulmoides, Ilex pernyi, Kandelia candel, Lawsonia inermis, Ligustrum obtusifolium, Narthecium asiaticum, Nolina microcarpa, Sambucus racemosa, Sargentodoxa cuneata, Saussurea medusa, Strychnos axillaris, Syringa reticulata, Tinospora sinensis, Veronica thymoides, Viscum coloratum and Vitex glabrata. They include 1-aryltetralin lactones (+)-syringaresinol beta-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006262D          

 43 47  0  0  1  0            999 V2000
   13.4272   -7.8736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2591   -7.8424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2011   -8.6637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1418   -7.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888   -7.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5341   -8.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4806   -9.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8867   -9.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7997   -6.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1502   -6.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4840   -9.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7740   -8.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8636   -6.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1502   -5.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7740  -10.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0570   -9.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5771   -6.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8636   -5.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0570   -9.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7774  -11.1420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3400   -8.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5771   -5.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2907   -6.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3191  -10.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4875  -11.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6265   -9.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3986   -5.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0075   -6.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4804  -10.8287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7703  -10.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4804  -11.6570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0534  -10.8287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7703  -12.0677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2008  -12.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0534  -11.6570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3433  -10.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7703  -12.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433  -12.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6368  -10.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5954   -7.9189    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0910   -7.8249    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8636   -4.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5847   -4.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  6  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  6  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  1  0  0  0  0
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 19 24  1  0  0  0  0
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 23 28  1  0  0  0  0
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 31 34  1  6  0  0  0
 32 35  1  0  0  0  0
 32 36  1  1  0  0  0
 33 37  1  1  0  0  0
 35 38  1  6  0  0  0
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  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
 16 19  1  0  0  0  0
 18 22  2  0  0  0  0
 33 35  1  0  0  0  0
  1 40  1  6  0  0  0
  2 41  1  6  0  0  0
 18 42  1  0  0  0  0
  1  2  1  0  0  0  0
 42 43  1  0  0  0  0
M  END

     RDKit          3D

 77 81  0  0  0  0  0  0  0  0999 V2000
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   -7.4675   -0.7705   -1.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1175   -0.7193   -1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2833   -0.3931    0.4799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9827   -1.0602    1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -0.8708    1.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -1.1506    0.3337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2908   -0.0096   -0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1433   -0.0673    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3547   -1.0311   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7038    2.0842   -1.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1652    1.2621    1.4989 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5676    1.9687    2.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    0.8212    1.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    1.7398    2.3090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6282    2.6899    2.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    0.8357    1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -0.1253   -1.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3594   -1.0480   -0.4862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6471   -0.1928    1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0133   -0.2327    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9932    0.0098    1.7496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5709    0.3039    3.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4148   -0.5219   -0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7863   -0.5553   -0.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5554   -3.5579   -1.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9374   -1.5383   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3386    2.8246   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1271    3.7778    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2092    2.8391    2.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  8  1  0
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 41 77  1  0
 39 74  1  0
 39 75  1  0
 39 76  1  0
 36 73  1  0
M  END


  Mrv1652309272006262D          

 43 47  0  0  1  0            999 V2000
   13.4272   -7.8736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2591   -7.8424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2011   -8.6637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1418   -7.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4888   -7.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5341   -8.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4806   -9.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8867   -9.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7997   -6.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1502   -6.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4840   -9.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7740   -8.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1502   -5.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7740  -10.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0570   -9.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5771   -6.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8636   -5.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0570   -9.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7774  -11.1420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3400   -8.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5771   -5.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2907   -6.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3191  -10.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4875  -11.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6265   -9.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3986   -5.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0075   -6.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4804  -10.8287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7703  -10.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4804  -11.6570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0534  -10.8287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7703  -12.0677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2008  -12.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0534  -11.6570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3433  -10.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7703  -12.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433  -12.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6368  -10.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5954   -7.9189    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0910   -7.8249    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8636   -4.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5847   -4.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  6  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  6  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
 23 28  1  0  0  0  0
 29 24  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  6  0  0  0
 32 35  1  0  0  0  0
 32 36  1  1  0  0  0
 33 37  1  1  0  0  0
 35 38  1  6  0  0  0
 36 39  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
 16 19  1  0  0  0  0
 18 22  2  0  0  0  0
 33 35  1  0  0  0  0
  1 40  1  6  0  0  0
  2 41  1  6  0  0  0
 18 42  1  0  0  0  0
  1  2  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CO[C@H](C3=CC(OC)=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(OC)=C3)[C@@]1([H])CO[C@@H]2C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O13/c1-34-16-5-12(6-17(35-2)21(16)30)25-14-10-39-26(15(14)11-38-25)13-7-18(36-3)27(19(8-13)37-4)41-28-24(33)23(32)22(31)20(9-29)40-28/h5-8,14-15,20,22-26,28-33H,9-11H2,1-4H3/t14-,15-,20+,22+,23-,24+,25+,26+,28-/m0/s1

> <INCHI_KEY>
WEKCEGQSIIQPAQ-IRBNZIFYSA-N

> <FORMULA>
C28H36O13

> <MOLECULAR_WEIGHT>
580.583

> <EXACT_MASS>
580.215591219

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.525946082570314

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
-0.3056510773333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200381847625739

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.302448560783015

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662076965

> <JCHEM_POLAR_SURFACE_AREA>
174.99

> <JCHEM_REFRACTIVITY>
140.17100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acanthoside B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      25.064 -14.697   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.617 -14.639   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.642 -16.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.531 -13.236   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.046 -13.158   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.130 -16.088   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.297 -16.952   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      25.922 -17.036   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      25.759 -12.287   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      28.280 -12.274   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.304 -18.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.978 -16.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.612 -13.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.280 -10.734   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.978 -19.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.640 -16.945   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.944 -12.274   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.612  -9.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.640 -18.485   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.985 -20.798   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      19.301 -16.172   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      30.944 -10.734   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      32.276 -13.047   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      19.262 -19.278   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.310 -21.558   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.970 -16.945   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      32.477  -9.688   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      33.614 -12.274   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.697 -20.213   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.371 -19.447   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.697 -21.760   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.033 -20.213   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.371 -22.526   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      19.041 -22.526   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.033 -21.760   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.707 -19.440   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.371 -24.060   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.707 -22.526   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.389 -20.213   0.000  0.00  0.00           O+0
HETATM   40  H   UNK     0      23.511 -14.782   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      28.170 -14.607   0.000  0.00  0.00           H+0
HETATM   42  O   UNK     0      29.612  -8.407   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      30.958  -7.630   0.000  0.00  0.00           C+0
CONECT    1    3    4   40    2                                             
CONECT    2    5    6   41    1                                             
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2    8                                                       
CONECT    7    3   11   12                                                  
CONECT    8    3    6                                                       
CONECT    9    4    5                                                       
CONECT   10    5   13   14                                                  
CONECT   11    7   15                                                       
CONECT   12    7   16                                                       
CONECT   13   10   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19   20                                                  
CONECT   16   12   21   19                                                  
CONECT   17   13   22   23                                                  
CONECT   18   14   22   42                                                  
CONECT   19   15   24   16                                                  
CONECT   20   15   25                                                       
CONECT   21   16   26                                                       
CONECT   22   17   27   18                                                  
CONECT   23   17   28                                                       
CONECT   24   19   29                                                       
CONECT   25   20                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29   24   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29   33   34                                                  
CONECT   32   30   35   36                                                  
CONECT   33   31   37   35                                                  
CONECT   34   31                                                            
CONECT   35   32   38   33                                                  
CONECT   36   32   39                                                       
CONECT   37   33                                                            
CONECT   38   35                                                            
CONECT   39   36                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42   18   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
(+)-Syringaresinol O-beta-D-glucoside	ChEBI
Acanthoside b	ChEBI
(+)-Syringaresinol O-b-D-glucoside	Generator
(+)-Syringaresinol O-β-D-glucoside	Generator
(+)-Syringaresinol b-D-glucoside	Generator
(+)-Syringaresinol β-D-glucoside	Generator
Eleutheroside E1	PhytoBank
(+)-Syringaresinol 4'-O-beta-glucopyranoside	PhytoBank
(+)-Syringaresinol 4'-O-β-glucopyranoside	PhytoBank
(+)-Syringaresinol 4’-O-β-glucopyranoside	PhytoBank
(+)-Syringaresinol O-beta-D-glucopyranoside	PhytoBank
(+)-Syringaresinol O-β-D-glucopyranoside	PhytoBank
(+)-Syringaresinol beta-D-glucopyranoside	PhytoBank
(+)-Syringaresinol β-D-glucopyranoside	PhytoBank
(+)-Syringaresinol beta-D-glucoside	PhytoBank
Syringaresinol 4'-O-beta-D-glucopyranoside	PhytoBank
Syringaresinol 4'-O-β-D-glucopyranoside	PhytoBank
Syringaresinol 4’-O-β-D-glucopyranoside	PhytoBank
Syringaresinol beta-D-glucoside	PhytoBank
Syringaresinol β-D-glucoside	PhytoBank
Syringaresinol 4'-O-glucopyranoside	PhytoBank
Syringaresinol 4’-O-glucopyranoside	PhytoBank
Syringaresinol 4'-O-glucoside	PhytoBank
Syringaresinol 4’-O-glucoside	PhytoBank

Chemical Formula

C₂₈H₃₆O₁₃

Average Mass

580.5830 Da

Monoisotopic Mass

580.21559 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

acanthoside B

CAS Registry Number

Not Available

SMILES

[H][C@]12CO[C@H](C3=CC(OC)=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(OC)=C3)[C@@]1([H])CO[C@@H]2C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C28H36O13/c1-34-16-5-12(6-17(35-2)21(16)30)25-14-10-39-26(15(14)11-38-25)13-7-18(36-3)27(19(8-13)37-4)41-28-24(33)23(32)22(31)20(9-29)40-28/h5-8,14-15,20,22-26,28-33H,9-11H2,1-4H3/t14-,15-,20+,22+,23-,24+,25+,26+,28-/m0/s1

InChI Key

WEKCEGQSIIQPAQ-IRBNZIFYSA-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
Acanthus ilicifolius	LOTUS Database	35616633
Acer saccharum	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Beaumontia grandiflora	LOTUS Database	35616633
Cananga odorata	LOTUS Database	35616633
Casearia sylvestris	LOTUS Database	35616633
Cistanche salsa	LOTUS Database	35616633
Cistanche tubulosa	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Daphne feddei	LOTUS Database	35616633
Dendrobium moniliforme	LOTUS Database	35616633
Dendrobium nobile	LOTUS Database	35616633
Desfontainia spinosa	LOTUS Database	35616633
Eleutherococcus senticosus	LOTUS Database	35616633
Epimedium grandiflorum	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Ilex pernyi	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Lawsonia inermis	LOTUS Database	35616633
Ligustrum obtusifolium	LOTUS Database	35616633
Narthecium asiaticum	LOTUS Database	35616633
Nolina microcarpa	LOTUS Database	35616633
Sambucus racemosa	LOTUS Database	35616633
Sargentodoxa cuneata	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Strychnos axillaris	LOTUS Database	35616633
Syringa reticulata	LOTUS Database	35616633
Tinospora sinensis	LOTUS Database	35616633
Veronica thymoides	LOTUS Database	35616633
Viscum coloratum	LOTUS Database	35616633
Vitex glabrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Furanoid lignan
Furofuran lignan skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Hexose monosaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Furofuran
Methoxybenzene
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Dialkyl ether
Ether
Acetal
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:28603 )
Lignan glycosides (C10890 )

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	0.98	ALOGPS
logP	-0.31	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	174.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	140.17 m³·mol⁻¹	ChemAxon
Polarizability	58.53 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002632

Chemspider ID

391325

KEGG Compound ID

C10890

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443024

PDB ID

Not Available

ChEBI ID

28603

Good Scents ID

Not Available

References

General References

Showing NP-Card for Acanthoside B (NP0137620)

MOL for NP0137620 (Acanthoside B)

3D MOL for NP0137620 (Acanthoside B)

3D SDF for NP0137620 (Acanthoside B)

3D-SDF for NP0137620 (Acanthoside B)

PDB for NP0137620 (Acanthoside B)

3D PDB for NP0137620 (Acanthoside B)

SMILES for NP0137620 (Acanthoside B)

INCHI for NP0137620 (Acanthoside B)

Structure for NP0137620 (Acanthoside B)

3D Structure for NP0137620 (Acanthoside B)