NP-MRD: Showing NP-Card for (3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate (NP0244443)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 05:14:40 UTC

Updated at

2022-09-07 05:14:40 UTC

NP-MRD ID

NP0244443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate

Description

(3,4,5-Trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate belongs to the class of organic compounds known as terpene glycosides. (3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate is found in Catalpa bignonioides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone (3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201506362D          

 34 36  0  0  0  0            999 V2000
    2.2501   -2.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -4.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -5.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -5.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836   -5.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -5.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -6.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711   -7.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995   -7.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126   -8.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411   -9.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -9.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542   -9.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958  -11.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0804  -10.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6935  -11.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519  -10.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -9.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557   -6.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3688   -7.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272   -6.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -5.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141   -5.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -4.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231   -6.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6382   -6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9481   -6.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -5.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9877   -5.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592   -4.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331   -6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -6.8624    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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
  9 21  1  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  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    4.7056    1.3484   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3445    0.2525   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2221    0.1635   -1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    1.0435   -1.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3613    1.7125   -0.8095 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6325    0.7885   -0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989    1.3384    0.6379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5947    1.4188   -0.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    0.6045    0.4460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8297    1.2598    0.8411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3846    2.0502   -0.1298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    0.0212    1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8150   -0.0543    1.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3832    0.1783    3.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2401   -0.9682    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9051   -2.3223    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4384   -2.6532   -1.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1030   -0.4488   -0.5321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0113   -1.3374   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3999   -2.3929   -1.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238   -3.1261   -2.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1731    2.6386    1.3137 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1570    2.4555    2.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469    3.5550    0.7515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2524    4.3795   -0.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681    2.7741    0.0261 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7320    3.6147   -0.7591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1935   -0.9186   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3128   -0.7538    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -1.8245    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8429   -3.0885    0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679   -4.1632    0.6680 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.2596   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8879   -2.1776   -0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730    0.4865   -2.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8062    1.8140   -2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379    2.1766   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218    0.5903    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    0.0340    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    1.7437    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077    2.3630   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3910   -0.9799    1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5710    0.7550    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5113   -0.2539    3.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -3.0820    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6668   -2.4253    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2733   -2.1325   -1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5525    0.1404   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -1.7973   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2028   -0.6878   -1.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -3.2037   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8304   -1.9960   -2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8243   -3.4051   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508    3.2111    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    1.6521    2.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    4.1717    1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983    5.3356    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    2.4002    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115    4.1299   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734    0.2320    0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0274   -1.7273    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601   -5.0889    0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046   -4.2605   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0181   -2.3045   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
  5 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 22  7  1  0
 34 28  1  0
 21 53  1  0
 20 51  1  0
 20 52  1  0
 19 49  1  0
 19 50  1  0
 18 48  1  6
  9 39  1  1
  7 38  1  1
  5 37  1  6
  4 35  1  0
  4 36  1  0
 29 60  1  0
 30 61  1  0
 32 62  1  0
 33 63  1  0
 34 64  1  0
 26 58  1  1
 27 59  1  0
 24 56  1  1
 25 57  1  0
 22 54  1  1
 23 55  1  0
 10 40  1  1
 11 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
M  END


  Mrv1533004201506362D          

 34 36  0  0  0  0            999 V2000
    2.2501   -2.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -4.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -5.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -5.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836   -5.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -5.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -6.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711   -7.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995   -7.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126   -8.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411   -9.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -9.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542   -9.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958  -11.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0804  -10.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6935  -11.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519  -10.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -9.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557   -6.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3688   -7.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272   -6.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -5.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141   -5.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -4.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231   -6.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6382   -6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9481   -6.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -5.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9877   -5.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592   -4.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331   -6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -6.8624    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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
  9 21  1  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  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1C(OC2OC(COC(=O)C3=CC=C(O)C=C3)C(O)C(O)C2O)C(O)C(CO)=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O12/c23-6-5-12-13(7-24)14(8-25)16(27)20(12)34-22-19(30)18(29)17(28)15(33-22)9-32-21(31)10-1-3-11(26)4-2-10/h1-4,12,15-20,22-30H,5-9H2

> <INCHI_KEY>
UKKKMOPYFVRHGS-UHFFFAOYSA-N

> <FORMULA>
C22H30O12

> <MOLECULAR_WEIGHT>
486.47

> <EXACT_MASS>
486.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.597114900568926

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate

> <ALOGPS_LOGP>
-1.53

> <JCHEM_LOGP>
-2.725851019666667

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.189161680932722

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.497690300031186

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3833242512150434

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
114.32950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate

> <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  O   UNK     0       4.200  -5.505   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.200  -7.045   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.867  -7.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.867  -9.355   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.621 -10.260   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.156  -9.784   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.988 -10.815   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.668 -12.321   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.813 -13.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.492 -14.858   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.637 -15.888   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.317 -17.395   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.852 -17.871   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.461 -18.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.141 -19.932   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.285 -20.962   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.750 -20.486   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.895 -21.517   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.070 -18.980   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.926 -17.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.277 -12.876   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.422 -13.906   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.597 -11.369   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.062 -10.893   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.453 -10.339   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.773  -8.833   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.097 -11.725   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.191 -12.971   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.637 -11.725   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.112 -10.260   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.577  -9.784   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.897  -8.278   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.542 -12.971   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.073 -12.810   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    7   26                                                  
CONECT   26   25                                                            
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33                                                  
CONECT   30   29    4   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   29   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3,4,5-Trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoic acid	Generator

Chemical Formula

C₂₂H₃₀O₁₂

Average Mass

486.4700 Da

Monoisotopic Mass

486.17373 Da

IUPAC Name

(3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate

Traditional Name

(3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

OCCC1C(OC2OC(COC(=O)C3=CC=C(O)C=C3)C(O)C(O)C2O)C(O)C(CO)=C1CO

InChI Identifier

InChI=1S/C22H30O12/c23-6-5-12-13(7-24)14(8-25)16(27)20(12)34-22-19(30)18(29)17(28)15(33-22)9-32-21(31)10-1-3-11(26)4-2-10/h1-4,12,15-20,22-30H,5-9H2

InChI Key

UKKKMOPYFVRHGS-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

Species Name	Source	Reference
Catalpa bignonioides	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
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
11-noriridane monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-2.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	114.33 m³·mol⁻¹	ChemAxon
Polarizability	48.6 Å³	ChemAxon
Number of Rings	3	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 (3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate (NP0244443)

MOL for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

3D MOL for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

3D SDF for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

3D-SDF for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

PDB for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

3D PDB for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

SMILES for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

INCHI for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

Structure for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)

3D Structure for NP0244443 ((3,4,5-trihydroxy-6-{[2-hydroxy-5-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl]oxy}oxan-2-yl)methyl 4-hydroxybenzoate)