NP-MRD: Showing NP-Card for methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0222426)

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Record Information

Version

2.0

Created at

2022-09-06 00:15:35 UTC

Updated at

2022-09-06 00:15:35 UTC

NP-MRD ID

NP0222426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

Methyl 3-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate 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. methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate is found in Lonicera caerulea. Methyl 3-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201501082D          

 51 56  0  0  0  0            999 V2000
   -4.2868   -4.1250    0.0000 C   0  0  0  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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  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   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   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
    2.8579   -7.4250    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
    3.5724   -8.6625    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   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 O   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   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
    0.7145   -2.8875    0.0000 O   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 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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 43  1  0  0  0  0
 33 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 31 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 29 50  1  0  0  0  0
 50 51  1  0  0  0  0
 26 51  1  0  0  0  0
M  END


  Mrv1533004201501082D          

 51 56  0  0  0  0            999 V2000
   -4.2868   -4.1250    0.0000 C   0  0  0  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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  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   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   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
    2.8579   -7.4250    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
    3.5724   -8.6625    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   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 O   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   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
    0.7145   -2.8875    0.0000 O   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 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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 43  1  0  0  0  0
 33 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 31 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 29 50  1  0  0  0  0
 50 51  1  0  0  0  0
 26 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC1OCC2OC(OC3OC=C4C(CCOC4=O)C3C=C)C(O)C(O)C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O18/c1-4-13-15-6-7-43-29(41)17(15)10-45-30(13)50-33-26(39)24(37)27-20(48-33)12-44-21(49-27)8-16-14(5-2)31(46-11-18(16)28(40)42-3)51-32-25(38)23(36)22(35)19(9-34)47-32/h4-5,10-11,13-16,19-27,30-39H,1-2,6-9,12H2,3H3

> <INCHI_KEY>
HADYJKOVEHJYKM-UHFFFAOYSA-N

> <FORMULA>
C33H44O18

> <MOLECULAR_WEIGHT>
728.697

> <EXACT_MASS>
728.252764577

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
71.55939105841796

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-1.0464847923333354

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.485053210300212

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.937074398087205

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592513

> <JCHEM_POLAR_SURFACE_AREA>
247.81999999999994

> <JCHEM_REFRACTIVITY>
165.27739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.002  -4.620   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  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21    5   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   51                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   50                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   46                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   43                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   43                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36   42                                                  
CONECT   42   41                                                            
CONECT   43   37   33   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   31   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   29   51                                                  
CONECT   51   50   26                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4ah,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-D][1,3]dioxin-2-yl]methyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₃₃H₄₄O₁₈

Average Mass

728.6970 Da

Monoisotopic Mass

728.25276 Da

IUPAC Name

methyl 3-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC1OCC2OC(OC3OC=C4C(CCOC4=O)C3C=C)C(O)C(O)C2O1

InChI Identifier

InChI=1S/C33H44O18/c1-4-13-15-6-7-43-29(41)17(15)10-45-30(13)50-33-26(39)24(37)27-20(48-33)12-44-21(49-27)8-16-14(5-2)31(46-11-18(16)28(40)42-3)51-32-25(38)23(36)22(35)19(9-34)47-32/h4-5,10-11,13-16,19-27,30-39H,1-2,6-9,12H2,3H3

InChI Key

HADYJKOVEHJYKM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lonicera caerulea	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
Terpene lactone
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Monoterpenoid
Pyranodioxin
Delta valerolactone
Delta_valerolactone
Sugar acid
Meta-dioxane
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
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	-0.74	ALOGPS
logP	-1	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	247.82 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	165.28 m³·mol⁻¹	ChemAxon
Polarizability	71.56 Å³	ChemAxon
Number of Rings	6	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

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 methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0222426)

MOL for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D MOL for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D SDF for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D-SDF for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

PDB for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D PDB for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

SMILES for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

INCHI for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

Structure for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D Structure for NP0222426 (methyl 5-ethenyl-4-{[6-({4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)-7,8-dihydroxy-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl]methyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)