NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0173405)

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Record Information

Version

2.0

Created at

2022-09-03 10:32:05 UTC

Updated at

2022-09-03 10:32:06 UTC

NP-MRD ID

NP0173405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Ainsliaside D belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Ainsliaea cordifolia. Based on a literature review a small amount of articles have been published on Ainsliaside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212322D          

 29 31  0  0  1  0            999 V2000
    0.9440   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  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
    0.7145   -2.8875    0.0000 C   0  0  2  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   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 16 29  1  0  0  0  0
 29  2  1  1  0  0  0
  7 29  1  0  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -0.1229    1.7514    2.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626    0.6248    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    0.4039    3.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979   -0.6770    3.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1683   -1.4152    1.8525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5158   -1.6293    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6879   -0.4911    0.7157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4935    0.7473    0.8950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -1.2004   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728   -0.3027   -1.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0894    0.2755   -1.5384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9838    1.6960   -1.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    1.7703   -3.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8761    2.6976   -1.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2955    2.2400   -1.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894   -0.1484   -0.3036 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7895    0.5241   -0.1820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9499   -0.1959   -0.2342 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6928   -0.1303    0.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704   -1.1603    1.0687 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8777   -0.6394    1.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5587   -0.1029    2.9294 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8463   -1.9646   -0.1622 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0509   -3.1053   -0.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -1.1747   -1.4305 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1339   -0.7745   -1.7714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.0319   -1.3600 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2968    0.0768   -2.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -0.3310    0.9228 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7640    1.3865    2.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5161    2.5788    2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214    2.2602    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8544    1.0747    3.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768   -1.4335    3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8617   -0.2209    3.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528   -2.3316    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964   -2.5407    1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0868    1.0413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2816    0.6844    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8986    1.6382    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612   -2.0630   -0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8962   -1.5521   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -0.9125   -2.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    0.4841   -1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -0.2349   -2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458    0.9265   -4.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163    2.6949   -3.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4203    1.8094   -3.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9230    2.4687   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7042    3.6611   -1.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030    2.9782   -0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    3.2036   -1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215   -1.2272   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259   -1.2726   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533   -1.8658    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6101   -1.4546    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3333    0.0908    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100    0.6410    2.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8993   -2.3627   -0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -3.7796    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249   -1.8830   -2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1652   -0.6649   -2.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635    0.9089   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027   -0.8215   -2.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8863   -1.3069    1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 29  2  1  0
 29  7  1  0
 27 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  6
 16 53  1  6
 18 54  1  6
 20 55  1  1
 21 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  1
 24 60  1  0
 25 61  1  6
 26 62  1  0
 27 63  1  1
 28 64  1  0
 29 65  1  1
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
M  END


  Mrv1652309032212322D          

 29 31  0  0  1  0            999 V2000
    0.9440   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  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
    0.7145   -2.8875    0.0000 C   0  0  2  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   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 16 29  1  0  0  0  0
 29  2  1  1  0  0  0
  7 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@@H](O)[C@]2(C)CC[C@H]([C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]12)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O8/c1-10-5-6-13(23)21(4)8-7-11(20(2,3)27)18(14(10)21)29-19-17(26)16(25)15(24)12(9-22)28-19/h5,11-19,22-27H,6-9H2,1-4H3/t11-,12-,13-,14-,15-,16+,17-,18-,19+,21+/m1/s1

> <INCHI_KEY>
YRNLPCONKVILRY-WLDDEBSSSA-N

> <FORMULA>
C21H36O8

> <MOLECULAR_WEIGHT>
416.511

> <EXACT_MASS>
416.241018119

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
43.87784679912517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,4aR,5R,8aS)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.26

> <JCHEM_LOGP>
-0.7950605349999998

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.179648574494728

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208140396613928

> <JCHEM_PKA_STRONGEST_BASIC>
-2.80494218705976

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
104.85650000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,4aR,5R,8aS)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.762  -4.326   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.232  -4.414   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.772  -1.746   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   29                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   11   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₆O₈

Average Mass

416.5110 Da

Monoisotopic Mass

416.24102 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,4aR,5R,8aS)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,4aR,5R,8aS)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC1=CC[C@@H](O)[C@]2(C)CC[C@H]([C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]12)C(C)(C)O

InChI Identifier

InChI=1S/C21H36O8/c1-10-5-6-13(23)21(4)8-7-11(20(2,3)27)18(14(10)21)29-19-17(26)16(25)15(24)12(9-22)28-19/h5,11-19,22-27H,6-9H2,1-4H3/t11-,12-,13-,14-,15-,16+,17-,18-,19+,21+/m1/s1

InChI Key

YRNLPCONKVILRY-WLDDEBSSSA-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
Ainsliaea cordifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
Secondary alcohol
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.26	ALOGPS
logP	-0.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.86 m³·mol⁻¹	ChemAxon
Polarizability	43.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15071446

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-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0173405)

MOL for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0173405 ((2r,3r,4s,5s,6r)-2-{[(1s,2r,4ar,5r,8as)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)