NP-MRD: Showing NP-Card for 3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0157298)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 14:38:59 UTC

Updated at

2022-09-02 14:38:59 UTC

NP-MRD ID

NP0157298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

3-Hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. 3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Lilium auratum and Lilium mackliniae. 3-Hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517142D          

 30 31  0  0  0  0            999 V2000
   -2.8579   -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
   -1.4289   -4.1250    0.0000 C   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
    0.0000   -4.1250    0.0000 C   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   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 C   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
  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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 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
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    8.5992    2.8291    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8360    1.6878    0.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8104    0.8345   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5400    1.0984    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4808    0.2395   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384    0.5267    0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1297   -0.2192    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7939    0.1608    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    1.1904    1.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6622   -0.5915    0.3029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.2401    0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6811   -1.2030    0.3885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3844   -2.5922    0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3334   -2.4466    2.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -0.7971    0.9066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764   -0.6387   -0.0903 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1894    0.6883   -0.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610    1.0139   -0.7466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4957    2.5351   -0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4055    3.0563   -1.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4949    0.4321    0.1051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7263    0.8334   -0.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3542   -1.0510    0.0390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2238   -1.5927    1.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9797   -1.5698    0.2189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8401   -2.7059   -0.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7253   -0.8624   -0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0108   -1.1284   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0388   -0.2767   -1.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3071   -0.5609   -1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0183    2.4948    1.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5323    3.2727    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9759    3.5360    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3061    1.9658    0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023    1.4242    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1742   -1.0983   -0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473   -0.1018    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8639    0.7463    0.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -1.3176   -0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2814   -3.2130    0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4559   -3.0049    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -1.8198    2.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795   -0.8988   -1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4454    0.6541   -1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4687    2.8744   -1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4010    2.8121    0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1406    3.9529   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3629    0.7999    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4103    0.1273   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7982   -1.3818   -0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2993   -2.5735    0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9057   -1.9861    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4987   -2.4229   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9560   -1.5470   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1882   -1.9968   -1.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0962    0.0513   -1.2391 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  5 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29  3  1  0
 25 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  6
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  6
 18 44  1  6
 19 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  0
 23 50  1  6
 24 51  1  0
 25 52  1  1
 26 53  1  0
 27 54  1  0
 28 55  1  0
 30 56  1  0
M  END


  Mrv1533004171517142D          

 30 31  0  0  0  0            999 V2000
   -2.8579   -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
   -1.4289   -4.1250    0.0000 C   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
    0.0000   -4.1250    0.0000 C   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   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 C   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
  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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 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
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCC(CO)OC2OC(CO)C(O)C(O)C2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O11/c1-27-13-6-10(2-4-12(13)22)3-5-15(23)28-9-11(7-20)29-19-18(26)17(25)16(24)14(8-21)30-19/h2-6,11,14,16-22,24-26H,7-9H2,1H3

> <INCHI_KEY>
QZXPMZIZXXPWSU-UHFFFAOYSA-N

> <FORMULA>
C19H26O11

> <MOLECULAR_WEIGHT>
430.406

> <EXACT_MASS>
430.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.65259158191788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.80

> <JCHEM_LOGP>
-1.0371955376666657

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.21033035444174

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.865813196902597

> <JCHEM_PKA_STRONGEST_BASIC>
-2.975558428242702

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
100.94120000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27    5   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₆O₁₁

Average Mass

430.4060 Da

Monoisotopic Mass

430.14751 Da

IUPAC Name

3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OCC(CO)OC2OC(CO)C(O)C(O)C2O)=CC=C1O

InChI Identifier

InChI=1S/C19H26O11/c1-27-13-6-10(2-4-12(13)22)3-5-15(23)28-9-11(7-20)29-19-18(26)17(25)16(24)14(8-21)30-19/h2-6,11,14,16-22,24-26H,7-9H2,1H3

InChI Key

QZXPMZIZXXPWSU-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
Lilium auratum	LOTUS Database	35616633
Lilium mackliniae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroidal glycoside
Glycosyl compound
O-glycosyl compound
Dihydropyranone
Cyclohexenone
Oxepane
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Polyol
Carboxylic acid derivative
Acetal
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.8	ALOGPS
logP	-1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	100.94 m³·mol⁻¹	ChemAxon
Polarizability	42.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

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-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0157298)

MOL for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0157298 (3-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)