NP-MRD: Showing NP-Card for proteacin (NP0203422)

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Record Information

Version

2.0

Created at

2022-09-04 22:52:37 UTC

Updated at

2022-09-04 22:52:37 UTC

NP-MRD ID

NP0203422

Secondary Accession Numbers

None

Natural Product Identification

Common Name

proteacin

Description

(2S)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetonitrile belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. proteacin is found in Apis cerana. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose (2S)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetonitrile is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Proteacin
  Mrv1572004231619332D          

 33 35  0  0  0  0            999 V2000
    2.4576   -0.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7423    0.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -0.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1764    0.2602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0302   -0.1472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1696   -1.3931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8918   -0.1541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1798    1.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    0.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269   -0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883   -0.9824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1662   -2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6037    0.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -0.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234   -1.8038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5969   -1.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8746   -2.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158    0.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    1.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    1.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    1.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364    1.0919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2483    1.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5260    0.2772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9466    1.0680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2175   -0.1335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8243   -0.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260    0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6585    1.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -0.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6277   -0.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500    1.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  6  0  0  0
  5  9  1  0  0  0  0
  5 10  1  6  0  0  0
  6 11  1  0  0  0  0
  6 12  1  1  0  0  0
  7 13  1  1  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  3  0  0  0  0
 11 17  1  6  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  6  0  0  0
 26 29  1  0  0  0  0
 26 30  1  1  0  0  0
 27 31  1  1  0  0  0
 29 32  1  6  0  0  0
 30 33  1  0  0  0  0
  7 11  1  0  0  0  0
 20 21  1  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -2.0373   -4.0425    1.0939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356   -2.9422    0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552   -1.5371    0.3760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1347   -0.8855    1.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2676   -0.3918    0.6473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3883    0.9995    0.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3165    1.3546   -0.2732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3513    2.8442   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094    3.2976   -0.9421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6922    0.8310    0.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4935    1.1234   -1.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6206   -0.6934    0.1070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8270   -1.2219    0.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480   -0.9723    1.1714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4617   -2.3452    1.2832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308   -0.9304    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1900   -1.7053    0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769   -1.1346    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382    0.2103    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8187   -0.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0818    0.1931   -0.0194 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8308    0.7202    1.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0345    0.0326    1.1122 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7513    0.2892    2.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9330   -0.4358    2.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925    0.5158   -0.0357 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1828   -0.0076    0.0313 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2221    0.0355   -1.3133 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8630    0.5798   -2.4247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880    0.4775   -1.3402 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1223   -0.2822   -2.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4747    1.0074   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7571    0.4134    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -1.5155   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2459   -0.6434   -0.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724    0.8813   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7392    3.3958    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0675    3.0153   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    2.8487   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1379    1.2708    0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4080    0.7743   -1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2738   -1.0651   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7309   -2.0353    1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9088   -0.4723    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975   -2.6392    2.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809   -2.7762    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368   -1.7692    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033   -0.8903    0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635   -1.0451    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0385    1.3636    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1610   -0.0444    3.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8710   -1.2901    2.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673    1.6137   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4565   -0.2162   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2410   -1.0892   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2680    1.1812   -2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742    1.5446   -1.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7001    0.2794   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118    2.0608   -0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555    1.0459    0.0132 H   0  0  0  0  0  0  0  0  0  0  0  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  3  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19 32  1  0
 32 33  2  0
  5 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  7  1  0
 33 16  1  0
 30 21  1  0
  9 39  1  0
  8 37  1  0
  8 38  1  0
  7 36  1  6
  5 35  1  6
  3 34  1  6
 17 46  1  0
 18 47  1  0
 21 48  1  1
 23 49  1  6
 24 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  6
 27 54  1  0
 28 55  1  6
 29 56  1  0
 30 57  1  6
 31 58  1  0
 32 59  1  0
 33 60  1  0
 14 44  1  1
 15 45  1  0
 12 42  1  6
 13 43  1  0
 10 40  1  1
 11 41  1  0
M  END

Proteacin
  Mrv1572004231619332D          

 33 35  0  0  0  0            999 V2000
    2.4576   -0.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7423    0.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -0.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1764    0.2602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0302   -0.1472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1696   -1.3931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8918   -0.1541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1798    1.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    0.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269   -0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883   -0.9824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1662   -2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6037    0.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -0.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234   -1.8038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5969   -1.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8746   -2.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158    0.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    1.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    1.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    1.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364    1.0919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2483    1.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5260    0.2772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9466    1.0680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2175   -0.1335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8243   -0.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260    0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6585    1.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -0.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6277   -0.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500    1.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  6  0  0  0
  5  9  1  0  0  0  0
  5 10  1  6  0  0  0
  6 11  1  0  0  0  0
  6 12  1  1  0  0  0
  7 13  1  1  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  3  0  0  0  0
 11 17  1  6  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  6  0  0  0
 26 29  1  0  0  0  0
 26 30  1  1  0  0  0
 27 31  1  1  0  0  0
 29 32  1  6  0  0  0
 30 33  1  0  0  0  0
  7 11  1  0  0  0  0
 20 21  1  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO12/c21-5-10(31-20-18(29)16(27)14(25)12(7-23)33-20)8-1-3-9(4-2-8)30-19-17(28)15(26)13(24)11(6-22)32-19/h1-4,10-20,22-29H,6-7H2/t10-,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1

> <INCHI_KEY>
RJPLGQRRNXUSQI-UUGBRMIUSA-N

> <FORMULA>
C20H27NO12

> <MOLECULAR_WEIGHT>
473.431

> <EXACT_MASS>
473.153325313

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.57953060790703

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetonitrile

> <ALOGPS_LOGP>
-1.49

> <JCHEM_LOGP>
-3.388684549333333

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.424990828525882

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.903182586890525

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084265018608

> <JCHEM_POLAR_SURFACE_AREA>
222.54999999999995

> <JCHEM_REFRACTIVITY>
104.22169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
proteacin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Proteacin                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-16         0                                  
HETATM    1  C   UNK     0       4.588  -0.275   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.252   0.498   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.581  -1.821   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.929   0.486   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.923  -0.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.917  -2.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.265  -0.288   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.936   2.013   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.594   0.492   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.917  -1.821   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.258  -1.834   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.910  -4.128   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.594   0.473   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.747  -0.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.607   2.032   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.910  -3.367   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       8.581  -2.600   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.233  -4.901   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.083   0.505   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.728   2.811   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.076   2.045   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.399   2.818   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.735   2.038   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.063   2.767   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.715   0.517   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.367   1.994   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.006  -0.249   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.405  -0.217   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -7.329   0.479   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.696   2.728   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.006  -1.757   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.638  -0.288   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -9.987   1.955   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9   10                                                  
CONECT    6    3   11   12                                                  
CONECT    7    4   13   11                                                  
CONECT    8    4                                                            
CONECT    9    5   14   15                                                  
CONECT   10    5   16                                                       
CONECT   11    6   17    7                                                  
CONECT   12    6   18                                                       
CONECT   13    7                                                            
CONECT   14    9   19                                                       
CONECT   15    9   20                                                       
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   14   21                                                       
CONECT   20   15   21                                                       
CONECT   21   19   22   20                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23   27   28                                                  
CONECT   26   24   29   30                                                  
CONECT   27   25   31   29                                                  
CONECT   28   25                                                            
CONECT   29   26   32   27                                                  
CONECT   30   26   33                                                       
CONECT   31   27                                                            
CONECT   32   29                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₇NO₁₂

Average Mass

473.4310 Da

Monoisotopic Mass

473.15333 Da

IUPAC Name

(2S)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetonitrile

Traditional Name

proteacin

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H27NO12/c21-5-10(31-20-18(29)16(27)14(25)12(7-23)33-20)8-1-3-9(4-2-8)30-19-17(28)15(26)13(24)11(6-22)32-19/h1-4,10-20,22-29H,6-7H2/t10-,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1

InChI Key

RJPLGQRRNXUSQI-UUGBRMIUSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Phenolic glycoside
O-glycosyl compound
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Polyol
Nitrile
Carbonitrile
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cyanogenic glycoside (CHEBI:8525 )
Cyanogenic glucosides derived from thyrosine (C08339 )

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	-3.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	222.55 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.22 m³·mol⁻¹	ChemAxon
Polarizability	44.58 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

C00001453

Chemspider ID

Not Available

KEGG Compound ID

C08339

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

656521

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for proteacin (NP0203422)

MOL for NP0203422 (proteacin)

3D MOL for NP0203422 (proteacin)

3D SDF for NP0203422 (proteacin)

3D-SDF for NP0203422 (proteacin)

PDB for NP0203422 (proteacin)

3D PDB for NP0203422 (proteacin)

SMILES for NP0203422 (proteacin)

INCHI for NP0203422 (proteacin)

Structure for NP0203422 (proteacin)

3D Structure for NP0203422 (proteacin)