NP-MRD: Showing NP-Card for [5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate (NP0320687)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 22:28:58 UTC

Updated at

2022-09-11 22:28:58 UTC

NP-MRD ID

NP0320687

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate

Description

[5-({4,5-Dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. [5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate is found in Cucurbita pepo. [5-({4,5-Dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500362D          

 38 41  0  0  0  0            999 V2000
    3.4666   -8.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -7.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612   -7.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762   -6.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8558   -6.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -6.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -5.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215   -4.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -4.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9346   -5.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7551   -5.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0906   -6.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9111   -6.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400   -5.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605   -5.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -4.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893   -3.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0839   -4.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -3.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -2.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.8852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -2.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458   -1.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -1.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938   -1.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868   -1.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722   -0.7325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    0.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516    1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996    1.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    1.6213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623    0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784   -2.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -1.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269   -5.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -6.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 23 35  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
  4 38  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -5.0026   -3.2242   -0.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3872   -2.1012   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811   -1.0508   -0.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1364   -1.2217   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405    0.1161   -0.2942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5279    0.4949   -1.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9846    1.1128    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9549    1.7951    1.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579    1.3568    0.7525 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1862    1.1428    1.7466 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399    1.8590    1.6077 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5879    1.0070    1.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9615    0.9315    0.1673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482   -0.1071   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613    0.0890   -2.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5403   -0.9687   -2.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103   -2.2457   -2.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3157   -3.3690   -3.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310   -3.9089   -3.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6568   -2.8965   -3.5938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982   -2.4431   -1.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7225   -1.3762   -0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926    1.4363    2.3447 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9434    2.7603    2.1656 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8913    3.1233    3.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2468    2.9500    4.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.6951    2.2986 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4608    4.3189    1.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    2.8254    2.7527 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4743    3.5604    3.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    0.0318    0.0630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7605   -1.0099    0.9655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7505   -1.8583   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6340   -2.9041   -1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9305   -2.6773   -1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3262   -1.4203   -1.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4249   -0.4245   -1.7770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1528   -0.6089   -1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347   -1.6169    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6458   -1.9756   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3398    1.4374   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.7401    0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5341    0.5342    1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    2.0829   -0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473    2.4797    0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991    0.0086    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231    1.0971   -2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8709   -0.8233   -3.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1698   -2.9740   -4.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -4.1406   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -4.2603   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -4.6914   -4.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0425   -2.5416   -2.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5404   -3.4691   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906   -1.5874    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918    2.9684    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363    4.1696    3.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663    2.4371    3.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151    3.8273    4.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9014    4.4761    3.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667    4.5355    0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754    2.2697    3.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087    4.5172    3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544   -0.0849   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0148   -0.7879    1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3199   -3.9199   -0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6025   -3.5245   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3330   -1.2195   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4516    0.2464   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  6
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
  5 31  1  0
 31 32  1  0
 14 22  1  0
 22 21  2  0
 21 17  1  0
 11 12  1  0
 31  9  1  0
 38 33  1  0
 20 53  1  0
 19 51  1  0
 19 52  1  0
 18 49  1  0
 18 50  1  0
 16 48  1  0
 15 47  1  0
 12 46  1  1
 24 56  1  6
 25 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  1
 28 61  1  0
 29 62  1  1
 30 63  1  0
 11 45  1  6
  9 44  1  6
  7 42  1  0
  7 43  1  0
  6 41  1  0
  4 39  1  0
  4 40  1  0
 34 66  1  0
 35 67  1  0
 36 68  1  0
 38 69  1  0
 31 64  1  6
 32 65  1  0
 22 55  1  0
 21 54  1  0
M  END


  Mrv1533004261500362D          

 38 41  0  0  0  0            999 V2000
    3.4666   -8.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -7.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612   -7.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762   -6.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8558   -6.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -6.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -5.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215   -4.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -4.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9346   -5.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7551   -5.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0906   -6.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9111   -6.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400   -5.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605   -5.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -4.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893   -3.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0839   -4.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -3.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -2.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.8852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -2.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458   -1.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -1.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938   -1.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868   -1.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722   -0.7325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    0.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516    1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996    1.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    1.6213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623    0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784   -2.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -1.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269   -5.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -6.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 23 35  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
  4 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320687

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1=CC=C(OC2OC(CO)C(O)C(O)C2OC2OCC(O)(COC(=O)C3=CC=CN=C3)C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO12/c27-9-7-14-3-5-16(6-4-14)36-23-20(19(30)18(29)17(11-28)37-23)38-24-21(31)25(33,13-35-24)12-34-22(32)15-2-1-8-26-10-15/h1-6,8,10,17-21,23-24,27-31,33H,7,9,11-13H2

> <INCHI_KEY>
SXPOXYLEVCBOBE-UHFFFAOYSA-N

> <FORMULA>
C25H31NO12

> <MOLECULAR_WEIGHT>
537.518

> <EXACT_MASS>
537.184625442

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.81844347446102

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-1.075947799666666

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.64518461835278

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.792988355974312

> <JCHEM_PKA_STRONGEST_BASIC>
3.24186812750984

> <JCHEM_POLAR_SURFACE_AREA>
197.48999999999998

> <JCHEM_REFRACTIVITY>
126.08949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0       6.471 -15.192   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.566 -13.946   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.034 -14.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.129 -12.861   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.597 -13.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.692 -11.776   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.319 -10.369   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.413  -9.123   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.118  -9.284   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.745 -10.691   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.276 -10.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.902 -12.259   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.434 -12.420   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.181  -9.606   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.713  -9.767   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.555  -8.199   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.460  -6.954   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.023  -8.038   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.397  -6.632   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.302  -5.386   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.842  -5.386   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.318  -3.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.072  -3.016   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.103  -1.871   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.042  -1.871   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.535  -2.192   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.495  -1.047   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.001  -1.367   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.019   0.417   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.487   0.738   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.963   2.202   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.933   3.347   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       0.574   3.027   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       1.050   1.562   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.826  -3.921   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.362  -3.445   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.850 -10.208   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.755 -11.454   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   38                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   23   20   36                                                  
CONECT   36   35                                                            
CONECT   37    7   38                                                       
CONECT   38   37    4                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
[5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₁NO₁₂

Average Mass

537.5180 Da

Monoisotopic Mass

537.18463 Da

IUPAC Name

[5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate

Traditional Name

[5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

OCCC1=CC=C(OC2OC(CO)C(O)C(O)C2OC2OCC(O)(COC(=O)C3=CC=CN=C3)C2O)C=C1

InChI Identifier

InChI=1S/C25H31NO12/c27-9-7-14-3-5-16(6-4-14)36-23-20(19(30)18(29)17(11-28)37-23)38-24-21(31)25(33,13-35-24)12-34-22(32)15-2-1-8-26-10-15/h1-6,8,10,17-21,23-24,27-31,33H,7,9,11-13H2

InChI Key

SXPOXYLEVCBOBE-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
Cucurbita pepo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxepane
Monosaccharide
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Hemiacetal
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
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	-0.46	ALOGPS
logP	-1.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	197.49 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.09 m³·mol⁻¹	ChemAxon
Polarizability	53.82 Å³	ChemAxon
Number of Rings	4	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

72989832

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate (NP0320687)

MOL for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

3D MOL for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

3D SDF for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

3D-SDF for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

PDB for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

3D PDB for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

SMILES for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

INCHI for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

Structure for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)

3D Structure for NP0320687 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl pyridine-3-carboxylate)