NP-MRD: Showing NP-Card for [3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate (NP0187489)

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Record Information

Version

2.0

Created at

2022-09-04 03:40:04 UTC

Updated at

2022-09-04 03:40:04 UTC

NP-MRD ID

NP0187489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Description

[3,4,5-Trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21. [3,4,5-Trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181503002D          

 32 34  0  0  0  0            999 V2000
    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 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 C   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
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 17 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -7.5376    1.6607    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6589    2.5974    0.7411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3124    2.2992    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4536    3.2520    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319    2.9130    1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738    3.8665    2.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6891    1.6419    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5301    0.6974    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437   -0.5513    0.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8989   -1.1611    0.5420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5388   -1.5184   -0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1593   -1.6945   -0.8693 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4566   -0.3538   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649   -0.4235   -1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696    0.6635   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1772    1.8038   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054    0.4930   -1.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587    1.5630   -1.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309    1.4097   -1.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1878    2.5063   -2.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8867    0.1537   -1.7343 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2624    0.0224   -1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0681   -0.9373   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6604   -2.1862   -1.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022   -0.7638   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -2.3371    0.3747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9543   -1.4231    1.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6225   -3.1746    1.0839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1185   -3.6126    2.3110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9024   -2.4309    1.3688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0517   -2.1529    2.7258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589    1.0422    0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5195    2.1557    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1546    1.3056   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6760    0.7569    0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8683    4.2137    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981    4.4678    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    1.4238    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -0.4418    0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547   -2.3346   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2427    0.3674   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0026    0.0951   -2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5175    2.5420   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8274    3.4494   -2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8913    0.7763   -1.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918   -3.0098   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -1.6107   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217   -3.0214    0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290   -1.5207    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186   -4.0853    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -4.2790    2.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7494   -3.0516    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9823   -2.3693    3.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5481    0.3057    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 12 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  8 32  2  0
 32  3  1  0
 30 10  1  0
 25 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
 10 39  1  1
 12 40  1  6
 13 41  1  0
 13 42  1  0
 18 43  1  0
 20 44  1  0
 22 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  6
 27 49  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  6
 31 53  1  0
 32 54  1  0
M  END


  Mrv1533004181503002D          

 32 34  0  0  0  0            999 V2000
    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 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 C   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
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 17 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O12/c1-29-10-4-9(21)5-11(6-10)31-20-18(27)17(26)16(25)14(32-20)7-30-19(28)8-2-12(22)15(24)13(23)3-8/h2-6,14,16-18,20-27H,7H2,1H3

> <INCHI_KEY>
BRZRXPMAXNSUND-UHFFFAOYSA-N

> <FORMULA>
C20H22O12

> <MOLECULAR_WEIGHT>
454.384

> <EXACT_MASS>
454.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.60099651987339

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.5249796973333336

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.413848279482714

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.08617185342463

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491104814649615

> <JCHEM_POLAR_SURFACE_AREA>
195.59999999999997

> <JCHEM_REFRACTIVITY>
104.39210000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001 -25.410   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334 -23.870   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000 -18.480   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   17                                                       
CONECT   26   12   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   10   31                                                  
CONECT   31   30                                                            
CONECT   32    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
[3,4,5-Trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₀H₂₂O₁₂

Average Mass

454.3840 Da

Monoisotopic Mass

454.11113 Da

IUPAC Name

[3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

[3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)=C1

InChI Identifier

InChI=1S/C20H22O12/c1-29-10-4-9(21)5-11(6-10)31-20-18(27)17(26)16(25)14(32-20)7-30-19(28)8-2-12(22)15(24)13(23)3-8/h2-6,14,16-18,20-27H,7H2,1H3

InChI Key

BRZRXPMAXNSUND-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 gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Gelsemium alkaloids

Sub Class

Not Available

Direct Parent

Gelsemium alkaloids

Alternative Parents

Substituents

C21-norgelsemium skeleton
Indole or derivatives
Oxepane
Aralkylamine
Oxane
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organic nitrogen compound
Carbonyl group
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	0.5	ALOGPS
logP	0.52	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.09	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.39 m³·mol⁻¹	ChemAxon
Polarizability	42.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

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 [3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate (NP0187489)

MOL for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

PDB for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

Structure for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0187489 ([3,4,5-trihydroxy-6-(3-hydroxy-5-methoxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate)