NP-MRD: Showing NP-Card for 4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate (NP0306612)

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Record Information

Version

2.0

Created at

2022-09-10 23:11:48 UTC

Updated at

2022-09-10 23:11:48 UTC

NP-MRD ID

NP0306612

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate

Description

4,5-Dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. 4,5-Dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241503192D          

 32 35  0  0  0  0            999 V2000
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
  7 18  1  0  0  0  0
 11 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    2.8157    1.6672   -0.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521    1.0242    0.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669   -0.2654    0.7103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -0.8482   -0.5627 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4324   -1.2093   -0.7992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2853   -0.0628   -1.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666    0.2335   -0.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0512    1.4732    0.4299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9983    1.9296    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2029    1.3982    1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    0.3241    0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6488    0.2321   -0.7500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9940    1.4447   -1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118    2.2539   -2.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003    3.3223   -2.9798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2728    1.7350   -1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860    0.7351   -0.3702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8212    1.3020    0.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2467   -2.1320   -1.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567   -3.3103   -1.6014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5524   -4.2755   -2.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8282   -4.4813   -2.5562 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4260   -2.9655   -1.7963 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1732   -4.1306   -1.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -2.0172   -0.6878 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1095   -1.5598   -0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566    1.6318    2.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4763    0.9473    3.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948    1.5874    4.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813    2.8806    4.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4551    3.5469    3.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354    2.9043    2.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707   -0.0939   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0075   -1.5789    0.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2479   -0.5334    0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573    2.7317    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142    1.8001    2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -0.6530    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930   -0.6962   -1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    1.5809   -3.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    2.5973   -1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240    3.8691   -2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586    2.5562   -1.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2144   -0.1397   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5883    0.7091    0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   -3.7494   -0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -5.2386   -2.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7753   -3.8579   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -5.1025   -1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -2.4896   -2.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1012   -4.3835   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134   -2.5968    0.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050   -2.3233   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0943   -0.0684    3.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    1.0433    5.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3288    3.3211    5.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332    4.5515    3.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    3.4292    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 17  1  0
 17 18  1  0
 17 16  1  0
 16 13  2  0
 13 14  1  0
 14 15  1  0
 13 12  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
  4 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 20  1  0
 12  7  1  0
 32 27  1  0
 12 11  1  0
 22 49  1  0
 21 47  1  0
 21 48  1  0
 20 46  1  1
  5 34  1  1
  7 35  1  1
  9 36  1  0
 10 37  1  0
 11 38  1  1
 17 44  1  6
 18 45  1  0
 16 43  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 12 39  1  6
  4 33  1  6
 28 54  1  0
 29 55  1  0
 30 56  1  0
 31 57  1  0
 32 58  1  0
 25 52  1  1
 26 53  1  0
 23 50  1  6
 24 51  1  0
M  END


  Mrv1533004241503192D          

 32 35  0  0  0  0            999 V2000
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
  7 18  1  0  0  0  0
 11 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306612

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(OC(=O)C2=CC=CC=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O10/c23-9-12-8-14(25)13-6-7-29-21(16(12)13)32-22-19(18(27)17(26)15(10-24)30-22)31-20(28)11-4-2-1-3-5-11/h1-8,13-19,21-27H,9-10H2

> <INCHI_KEY>
OANONBNMFPNJOA-UHFFFAOYSA-N

> <FORMULA>
C22H26O10

> <MOLECULAR_WEIGHT>
450.44

> <EXACT_MASS>
450.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.79016201243236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.6865700536666667

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.870557925994252

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.686420673898844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.741445501840456

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
108.9988

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.877   4.625   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.121   6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.453   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.120   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.786   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.786   8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.120   9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.453   8.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.788   8.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
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   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    7   11                                                  
CONECT   19    5   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   19   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoic acid	Generator

Chemical Formula

C₂₂H₂₆O₁₀

Average Mass

450.4400 Da

Monoisotopic Mass

450.15260 Da

IUPAC Name

4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate

Traditional Name

4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(OC(=O)C2=CC=CC=C2)C(O)C1O

InChI Identifier

InChI=1S/C22H26O10/c23-9-12-8-14(25)13-6-7-29-21(16(12)13)32-22-19(18(27)17(26)15(10-24)30-22)31-20(28)11-4-2-1-3-5-11/h1-8,13-19,21-27H,9-10H2

InChI Key

OANONBNMFPNJOA-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Iridoid-skeleton
Aromatic monoterpenoid
Benzoate ester
Bicyclic monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.47	ALOGPS
logP	-0.69	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109 m³·mol⁻¹	ChemAxon
Polarizability	43.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate (NP0306612)

MOL for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D MOL for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D SDF for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D-SDF for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

PDB for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D PDB for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

SMILES for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

INCHI for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

Structure for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D Structure for NP0306612 (4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxan-3-yl benzoate)