NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0249935)

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Record Information

Version

2.0

Created at

2022-09-07 12:37:56 UTC

Updated at

2022-09-07 12:37:57 UTC

NP-MRD ID

NP0249935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

3'-Dehydroxynyasicoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Molineria capitulata. Based on a literature review very few articles have been published on 3'-Dehydroxynyasicoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214372D          

 33 35  0  0  1  0            999 V2000
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -5.1744   -2.5713   -2.0188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1109   -3.0502   -1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -1.9432   -0.4041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0153   -0.9262   -1.2232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052   -0.0230   -0.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3626    0.6660   -1.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0788    0.2726   -0.7428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3850   -0.7716   -1.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -1.2595   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193   -1.6984   -1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -2.2041   -0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1634   -2.1413   -1.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -2.6302   -1.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6343   -3.1856   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9169   -3.6551    0.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6076   -3.2562    0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3709   -2.7629    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567    1.3101   -0.7616 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1254    0.7021   -0.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403    2.5636   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8930    3.2163    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551    4.4206    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    5.0418    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136    6.2632    1.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823    4.4338    0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397    5.0253    1.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    3.2106    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    0.8231    0.3076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8086    1.2781    1.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6061    0.1159    0.4612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5087    0.3915   -0.5711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675   -1.3807    0.6203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1127   -1.7232    1.9179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9529   -1.6854   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5741   -3.8278   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3534   -3.5841   -1.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.3649    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105   -0.6811    0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452   -0.3621    0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -1.6228   -1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4609   -0.2494   -2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.7155   -2.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077   -2.5618   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1813   -4.0725    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -3.6912    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5659   -2.8262    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417    1.5363   -1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0763    0.7708    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    2.7790    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413    4.9268    1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691    6.6974    2.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939    5.9017    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    2.7712   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    1.7392   -0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7712    0.4939    2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0881    0.4866    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2425    0.9771   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4574   -1.8274    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5555   -2.5597    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  3  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  7 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
  5 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  3  1  0
 17 11  1  0
 27 20  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  1
  5 38  1  1
  7 39  1  1
  8 40  1  0
  8 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  6
 19 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  6
 29 55  1  0
 30 56  1  1
 31 57  1  0
 32 58  1  6
 33 59  1  0
M  END


  Mrv1652309072214372D          

 33 35  0  0  1  0            999 V2000
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0249935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H](CC#CC2=CC=C(O)C=C2)[C@H](O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O10/c24-11-18-20(29)21(30)22(31)23(33-18)32-17(3-1-2-12-4-7-14(25)8-5-12)19(28)13-6-9-15(26)16(27)10-13/h4-10,17-31H,3,11H2/t17-,18+,19+,20+,21-,22+,23+/m0/s1

> <INCHI_KEY>
OKZOQIQDXNCAIO-JLIHBVADSA-N

> <FORMULA>
C23H26O10

> <MOLECULAR_WEIGHT>
462.451

> <EXACT_MASS>
462.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.374799968604165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.44077488299999956

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.773632738719096

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.071309123726577

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835588052473

> <JCHEM_POLAR_SURFACE_AREA>
180.29999999999998

> <JCHEM_REFRACTIVITY>
111.86210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18    7   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20                                                       
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₁₀

Average Mass

462.4510 Da

Monoisotopic Mass

462.15260 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H](CC#CC2=CC=C(O)C=C2)[C@H](O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H26O10/c24-11-18-20(29)21(30)22(31)23(33-18)32-17(3-1-2-12-4-7-14(25)8-5-12)19(28)13-6-9-15(26)16(27)10-13/h4-10,17-31H,3,11H2/t17-,18+,19+,20+,21-,22+,23+/m0/s1

InChI Key

OKZOQIQDXNCAIO-JLIHBVADSA-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
Molineria capitulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxygen compound
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.44	ChemAxon
pKa (Strongest Acidic)	9.07	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	180.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.86 m³·mol⁻¹	ChemAxon
Polarizability	46.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

9013045

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10837746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0249935)

MOL for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0249935 ((2r,3r,4s,5s,6r)-2-{[(1r,2s)-1-(3,4-dihydroxyphenyl)-1-hydroxy-5-(4-hydroxyphenyl)pent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)