NP-MRD: Showing NP-Card for (2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate (NP0245049)

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Record Information

Version

2.0

Created at

2022-09-07 05:59:08 UTC

Updated at

2022-09-07 05:59:09 UTC

NP-MRD ID

NP0245049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate

Description

(2S,3S,4S,5S,6S)-4-(acetyloxy)-5-hydroxy-6-{[(2S,4S,5S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]Dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2E)-3-phenylprop-2-enoate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. (2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate is found in Gmelina arborea. Based on a literature review very few articles have been published on (2S,3S,4S,5S,6S)-4-(acetyloxy)-5-hydroxy-6-{[(2S,4S,5S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]Dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2E)-3-phenylprop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072207592D          

 48 53  0  0  1  0            999 V2000
    0.3130    4.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740    3.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    3.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1170    3.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1780    2.3418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9210    1.9832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6030    2.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819    1.1604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7249    0.8019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -0.0209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4874   -0.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8753   -0.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791   -1.5964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.8271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6907   -2.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2866   -3.1990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0786   -2.9683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -3.5389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4666   -3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -3.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -4.3402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0741   -4.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -4.5709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4899   -5.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -4.0003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2982   -4.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -1.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684   -1.3174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4430   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162   -2.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509   -1.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.5538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2999    0.6963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    1.0548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1251    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    1.8776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2471    2.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9291    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    0.9492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3541    1.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    2.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792    1.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5222    1.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832    2.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9011    3.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581    2.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 15 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 33 32  1  1  0  0  0
 10 33  1  0  0  0  0
 29 33  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 43 48  1  0  0  0  0
M  END


  Mrv1652309072207592D          

 48 53  0  0  1  0            999 V2000
    0.3130    4.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740    3.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    3.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1170    3.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1780    2.3418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9210    1.9832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6030    2.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819    1.1604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7249    0.8019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -0.0209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4874   -0.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8753   -0.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791   -1.5964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.8271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6907   -2.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2866   -3.1990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0786   -2.9683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -3.5389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4666   -3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -3.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -4.3402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0741   -4.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -4.5709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4899   -5.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -4.0003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2982   -4.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -1.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684   -1.3174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4430   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162   -2.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509   -1.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.5538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2999    0.6963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    1.0548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1251    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    1.8776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2471    2.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9291    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    0.9492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3541    1.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    2.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792    1.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5222    1.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832    2.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9011    3.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581    2.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 15 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 33 32  1  1  0  0  0
 10 33  1  0  0  0  0
 29 33  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 43 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H]3O[C@]3(CO)C3C2C=CO[C@H]3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](OC(C)=O)[C@H]1OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O16/c1-14-25(45-19(36)9-8-16-6-4-3-5-7-16)27(43-15(2)35)24(40)31(42-14)46-26-17-10-11-41-29(20(17)32(13-34)28(26)48-32)47-30-23(39)22(38)21(37)18(12-33)44-30/h3-11,14,17-18,20-31,33-34,37-40H,12-13H2,1-2H3/b9-8+/t14-,17?,18+,20?,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31-,32+/m0/s1

> <INCHI_KEY>
WUGDNVYHMVWTAP-PYOGHYBESA-N

> <FORMULA>
C32H40O16

> <MOLECULAR_WEIGHT>
680.656

> <EXACT_MASS>
680.231635208

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
66.63101961589992

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5S,6S)-4-(acetyloxy)-5-hydroxy-6-{[(2S,4S,5S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
-0.6807131603333345

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.516920602152325

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.964537339262034

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601929344

> <JCHEM_POLAR_SURFACE_AREA>
232.65999999999997

> <JCHEM_REFRACTIVITY>
156.78029999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5S,6S)-4-(acetyloxy)-5-hydroxy-6-{[(2S,4S,5S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.584   8.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.698   6.576   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.575   5.710   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.085   5.907   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.199   4.371   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.586   3.702   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.859   4.568   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.700   2.166   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.087   1.497   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.200  -0.039   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.510  -0.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.988  -0.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.101  -1.484   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.734  -2.980   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.256  -3.411   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.889  -4.906   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -5.971   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.480  -5.541   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.592  -6.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.071  -6.175   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.183  -7.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.226  -8.102   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.338  -9.167   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.747  -8.532   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.381 -10.028   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.635  -7.467   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.157  -7.898   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.143  -2.345   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.608  -2.459   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.560  -3.998   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.204  -4.727   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.082  -2.251   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.025  -1.034   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.426   1.300   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.040   1.969   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.234   1.103   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.926   3.505   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.461   4.174   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.734   3.308   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.621   1.772   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -3.121   3.977   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.394   3.111   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -5.781   3.780   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -7.054   2.913   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -8.441   3.583   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.555   5.118   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -7.282   5.985   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -5.895   5.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   15   11   29                                                  
CONECT   29   28   30   32   33                                             
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   10   29                                                  
CONECT   34    8   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    5   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   43                                                       
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4S,5S,6S)-4-(Acetyloxy)-5-hydroxy-6-{[(2S,4S,5S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0,]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₆

Average Mass

680.6560 Da

Monoisotopic Mass

680.23164 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H]3O[C@]3(CO)C3C2C=CO[C@H]3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](OC(C)=O)[C@H]1OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C32H40O16/c1-14-25(45-19(36)9-8-16-6-4-3-5-7-16)27(43-15(2)35)24(40)31(42-14)46-26-17-10-11-41-29(20(17)32(13-34)28(26)48-32)47-30-23(39)22(38)21(37)18(12-33)44-30/h3-11,14,17-18,20-31,33-34,37-40H,12-13H2,1-2H3/b9-8+/t14-,17?,18+,20?,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31-,32+/m0/s1

InChI Key

WUGDNVYHMVWTAP-PYOGHYBESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gmelina arborea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
O-glycosyl compound
Glycosyl compound
Styrene
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.68	ChemAxon
pKa (Strongest Acidic)	11.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	232.66 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	156.78 m³·mol⁻¹	ChemAxon
Polarizability	66.63 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

163189449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate (NP0245049)

MOL for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0245049 ((2s,3s,4s,5s,6s)-4-(acetyloxy)-5-hydroxy-6-{[(2s,4s,5s,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-2-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)