NP-MRD: Showing NP-Card for (2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate (NP0319217)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-11 20:08:18 UTC

Updated at

2022-09-11 20:08:19 UTC

NP-MRD ID

NP0319217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate

Description

O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate, also known as (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4’-(tri-acetylrhamnoside), 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. O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. (2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate is found in Moringa oleifera. This could make O-ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308011919542D          

 33 34  0  0  0  0            999 V2000
10013.101710014.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.959410015.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.674610015.3053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10017.387810015.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.101010015.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10018.816210015.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.387810016.5419    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10011.676010013.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.245810014.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.676010016.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.245810015.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.245810015.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.531410015.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.816810015.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.816810014.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.531210014.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.245810014.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.674410015.7185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.960010015.3059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.960010014.4810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.674410014.0686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.388910014.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.388910015.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.531110015.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.816010015.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.531710014.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.246710013.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.532210012.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.391410012.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.962110012.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.392610012.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.105710013.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.530910015.3045    0.0000 C   0  0  0  0  0  0  0  0  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
 12 13  2  0  0  0  0
 13 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 12  1  0  0  0  0
  1 15  1  0  0  0  0
 12  2  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 22 23  1  0  0  0  0
 22  1  1  1  0  0  0
 21  8  1  6  0  0  0
 20  9  1  6  0  0  0
 19 11  1  1  0  0  0
 18 10  1  6  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 31  1  0  0  0  0
 27 30  2  0  0  0  0
 29 32  2  0  0  0  0
  4  7  2  0  0  0  0
  6 33  1  0  0  0  0
M  END

     RDKit          3D

 62 63  0  0  0  0  0  0  0  0999 V2000
    9.8145    0.9120   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8979    2.1071   -0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5669    1.6473   -0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0899    0.8397    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0558    0.3333    1.6861 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    0.4448    0.4660 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    0.8953   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966    0.3925   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1346   -0.8085   -1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.3056   -0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -0.6231   -0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199   -1.1569   -0.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -0.6334    0.5019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0252   -1.4550    1.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2041   -2.0746    1.2318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6036   -2.8359    2.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541   -1.1003    0.9812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2094   -1.7184    0.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5407   -1.9443    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4523   -2.5988   -0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0170   -1.5895    1.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7949    0.1462    0.2767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3165    0.9937    1.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7957    2.2909    1.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2798    3.1809    2.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    2.7034    0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -0.3914   -0.5184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2439    0.4251   -1.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2797    0.0151   -2.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    0.8993   -4.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636   -1.1681   -3.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216    0.5725    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235    1.0784    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5743    0.9848   -1.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2113   -0.0057   -0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2869    0.8676    0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1449    2.7994   -1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9570    2.6852    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870   -0.1624    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372    0.5475   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    2.0012   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8966   -1.3587   -1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5597   -2.2552   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329    0.3399    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545   -2.8598    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621   -3.2172    2.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493   -2.1069    3.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100   -3.6448    2.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8820   -0.8334    1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9394   -1.7619   -1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2002   -3.2392   -0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8456   -3.1522   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5436    0.6177   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730    3.7086    2.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    3.9277    2.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    2.5899    3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9010   -1.3771   -0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637    0.3019   -4.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    1.1955   -4.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186    1.7599   -3.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    1.1538    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8114    2.0206    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 11 32  1  0
 32 33  2  0
 33  8  1  0
 27 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
 10 43  1  0
 13 44  1  1
 15 45  1  6
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  1
 20 50  1  0
 20 51  1  0
 20 52  1  0
 22 53  1  6
 25 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  6
 30 58  1  0
 30 59  1  0
 30 60  1  0
 32 61  1  0
 33 62  1  0
M  END


  Mrv1652308011919542D          

 33 34  0  0  0  0            999 V2000
10013.101710014.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.959410015.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.674610015.3053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10017.387810015.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.101010015.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10018.816210015.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.387810016.5419    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10011.676010013.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.245810014.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.676010016.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.245810015.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.245810015.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.531410015.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.816810015.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.816810014.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.531210014.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.245810014.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.674410015.7185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.960010015.3059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.960010014.4810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.674410014.0686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.388910014.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.388910015.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.531110015.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.816010015.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.531710014.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.246710013.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.532210012.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.391410012.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.962110012.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.392610012.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.105710013.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.530910015.3045    0.0000 C   0  0  0  0  0  0  0  0  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
 12 13  2  0  0  0  0
 13 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 12  1  0  0  0  0
  1 15  1  0  0  0  0
 12  2  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 22 23  1  0  0  0  0
 22  1  1  1  0  0  0
 21  8  1  6  0  0  0
 20  9  1  6  0  0  0
 19 11  1  1  0  0  0
 18 10  1  6  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 31  1  0  0  0  0
 27 30  2  0  0  0  0
 29 32  2  0  0  0  0
  4  7  2  0  0  0  0
  6 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO9S/c1-6-27-22(33)23-11-16-7-9-17(10-8-16)32-21-20(31-15(5)26)19(30-14(4)25)18(12(2)28-21)29-13(3)24/h7-10,12,18-21H,6,11H2,1-5H3,(H,23,33)/t12-,18-,19+,20+,21-/m0/s1

> <INCHI_KEY>
WYFYRQBBNVSDHV-CDEOHPBMSA-N

> <FORMULA>
C22H29NO9S

> <MOLECULAR_WEIGHT>
483.532

> <EXACT_MASS>
483.156302221

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.69879351345427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
2.582482312666666

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.69198359790125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.281671315053015

> <JCHEM_POLAR_SURFACE_AREA>
118.62

> <JCHEM_REFRACTIVITY>
118.37439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-AUG-19         0                                  
HETATM    1  O   UNK     0    8691.1238692.928   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8696.4588696.006   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8697.7938695.237   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8699.1248696.006   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8700.4558695.237   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8701.7908696.006   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0    8699.1248697.545   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0    8688.4628691.389   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8685.7928692.928   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8688.4628697.545   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8685.7928696.006   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8695.1258695.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8693.7928696.008   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8692.4588695.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8692.4588693.698   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8693.7928692.928   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8695.1258693.698   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8688.4598696.008   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8687.1258695.238   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8687.1258693.698   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8688.4598692.928   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8689.7938693.698   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8689.7938695.238   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0    8684.4588695.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8683.1238696.005   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8684.4598693.694   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0    8685.7948691.387   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8684.4608690.615   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8689.7978690.621   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8687.1298690.618   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8689.8008689.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8691.1318691.393   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8703.1248695.235   0.000  0.00  0.00           C+0
CONECT    1   15   22                                                       
CONECT    2    3   12                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5   33                                                       
CONECT    7    4                                                            
CONECT    8   21   29                                                       
CONECT    9   20   27                                                       
CONECT   10   18                                                            
CONECT   11   19   24                                                       
CONECT   12   13   17    2                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    1                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   19   23   10                                                  
CONECT   19   18   20   11                                                  
CONECT   20   19   21    9                                                  
CONECT   21   20   22    8                                                  
CONECT   22   21   23    1                                                  
CONECT   23   18   22                                                       
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    9   28   30                                                  
CONECT   28   27                                                            
CONECT   29    8   31   32                                                  
CONECT   30   27                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33    6                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-a-L-rhamnosyloxy)benzyl]thiocarbamate	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-a-L-rhamnosyloxy)benzyl]thiocarbamic acid	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamic acid	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamic acid	Generator
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetic acid	HMDB
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetate	HMDB
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetic acid	HMDB
(Z)-N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)	HMDB
(Z)-N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4’-(tri-acetylrhamnoside)	HMDB
(Z)-O-Ethyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
(Z)-O-Ethyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
(Z)-O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
(Z)-O-Ethyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)	HMDB
N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4’-(tri-acetylrhamnoside)	HMDB
O-Ethyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
O-Ethyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
O-Ethyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB

Chemical Formula

C₂₂H₂₉NO₉S

Average Mass

483.5320 Da

Monoisotopic Mass

483.15630 Da

IUPAC Name

(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate

Traditional Name

(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)C=C1

InChI Identifier

InChI=1S/C22H29NO9S/c1-6-27-22(33)23-11-16-7-9-17(10-8-16)32-21-20(31-15(5)26)19(30-14(4)25)18(12(2)28-21)29-13(3)24/h7-10,12,18-21H,6,11H2,1-5H3,(H,23,33)/t12-,18-,19+,20+,21-/m0/s1

InChI Key

WYFYRQBBNVSDHV-CDEOHPBMSA-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
Moringa oleifera	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

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Tricarboxylic acid or derivatives
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Thiocarbamic acid ester
Carboxylic acid ester
Thiocarbamic acid derivative
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organosulfur 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	3.3	ALOGPS
logP	2.58	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.62 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	118.37 m³·mol⁻¹	ChemAxon
Polarizability	49.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031946

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008633

KNApSAcK ID

Not Available

Chemspider ID

8498489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10323025

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,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate (NP0319217)

MOL for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

3D MOL for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

3D SDF for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

3D-SDF for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

PDB for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

3D PDB for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

SMILES for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

INCHI for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

Structure for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)

3D Structure for NP0319217 ((2s,3s,4r,5r,6s)-4,5-bis(acetyloxy)-6-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-2-methyloxan-3-yl acetate)