NP-MRD: Showing NP-Card for 3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one (NP0188494)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 04:50:12 UTC

Updated at

2022-09-04 04:50:12 UTC

NP-MRD ID

NP0188494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one

Description

5-(Hydroxymethyl)-4-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2,4,11,13,15-hexaen-6-one belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. 3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one is found in Nauclea officinalis. 5-(Hydroxymethyl)-4-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2,4,11,13,15-hexaen-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510292D          

 36 40  0  0  0  0            999 V2000
    2.9657   -0.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6999   -1.4026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946   -2.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7182   -2.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999   -0.8071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0579    0.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816    0.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    0.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -3.4718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -4.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  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
  6  7  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 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
 26 34  1  0  0  0  0
 29 34  1  0  0  0  0
 27 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  2  0  0  0  0
 17 36  1  0  0  0  0
M  END

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
   -1.6357   -2.2470    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930   -1.3504    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028   -0.0550    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072    0.6173    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968   -0.2450    0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0902    0.4353    0.1754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6583    0.4216   -1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608   -0.4756   -1.2952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1441   -1.8740   -1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3837   -1.7750   -2.8074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7439   -0.5364   -0.2731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9962   -0.1253   -0.7656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4172    0.3971    0.8728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2473    0.1504    1.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0083    0.0495    1.3068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9800   -1.2734    1.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764    0.6118    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -0.0327    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1981    0.5618    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2878    1.7985    0.6698 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    2.4564    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906    3.6276    1.5542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.8806    1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375    2.6901    1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    3.9569    2.0520 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386    2.4862    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    1.8053    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961    0.4486   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -0.1690   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5539   -1.4093   -0.8049 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8521   -1.6111   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846   -2.6565   -1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9522   -2.5792   -1.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6196   -1.4251   -1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8989   -0.3716   -0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5172   -0.4566   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -1.9646   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -2.2469    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2298   -3.3045   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4747   -1.8681    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    1.0168    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439    1.3232   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.5233    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1633   -0.1365   -2.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0142   -2.5487   -1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5022   -2.2783   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -2.5266   -2.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8640   -1.5533    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8382    0.1603   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5007    1.4557    0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5944    0.9706    2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7721    0.6368    2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218   -1.5657    2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003   -1.0240   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676    2.3016    2.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    2.9031    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    4.3973    2.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6832    2.7401    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4131    3.5125    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155    2.4138   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5656    1.7736    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697   -2.0788   -0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0473   -3.5647   -1.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5340   -3.4108   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7052   -1.3400   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3642    0.5561   -0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  3 17  1  0
 17 23  2  0
 23 24  1  0
 24 25  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 29 19  1  0
 19 18  2  0
 15  6  1  0
 18 17  1  0
 19 20  1  0
 36 28  1  0
 36 31  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  1
  8 44  1  6
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  1
 12 49  1  0
 13 50  1  6
 14 51  1  0
 15 52  1  1
 16 53  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 30 62  1  0
 32 63  1  0
 33 64  1  0
 34 65  1  0
 35 66  1  0
 18 54  1  0
M  END


  Mrv1533004241510292D          

 36 40  0  0  0  0            999 V2000
    2.9657   -0.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6999   -1.4026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946   -2.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7182   -2.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999   -0.8071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0579    0.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816    0.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    0.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -3.4718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -4.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  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
  6  7  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 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
 26 34  1  0  0  0  0
 29 34  1  0  0  0  0
 27 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  2  0  0  0  0
 17 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(COC1OC(CO)C(O)C(O)C1O)C1=C(CO)C(=O)N2CCC3=C(NC4=CC=CC=C34)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30N2O8/c1-2-13(12-35-26-24(33)23(32)22(31)20(11-30)36-26)16-9-19-21-15(14-5-3-4-6-18(14)27-21)7-8-28(19)25(34)17(16)10-29/h2-6,9,20,22-24,26-27,29-33H,7-8,10-12H2,1H3

> <INCHI_KEY>
XRSKCXMPZFQFCK-UHFFFAOYSA-N

> <FORMULA>
C26H30N2O8

> <MOLECULAR_WEIGHT>
498.532

> <EXACT_MASS>
498.200215934

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
53.032438822777216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-4H,6H,7H,12H-indolo[2,3-a]quinolizin-4-one

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
-1.3257951236666659

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.101880463837539

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.197765163696992

> <JCHEM_PKA_STRONGEST_BASIC>
-2.505929858746433

> <JCHEM_POLAR_SURFACE_AREA>
155.71

> <JCHEM_REFRACTIVITY>
132.10109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6H,7H,12H-indolo[2,3-a]quinolizin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.536  -0.891   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.923  -1.155   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.614  -1.243   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.307  -2.618   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.844  -2.706   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.537  -4.082   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.074  -4.170   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.689  -1.419   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.226  -1.507   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.996  -0.043   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.841   1.244   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.459   0.045   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.766   1.420   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.921  -5.105   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.228  -6.481   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.303  -6.305   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.611  -7.680   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       5.841  -6.217   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    3   18   36                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   26   29                                                  
CONECT   35   27   23   36                                                  
CONECT   36   35   17                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀N₂O₈

Average Mass

498.5320 Da

Monoisotopic Mass

498.20022 Da

IUPAC Name

3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-4H,6H,7H,12H-indolo[2,3-a]quinolizin-4-one

Traditional Name

3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6H,7H,12H-indolo[2,3-a]quinolizin-4-one

CAS Registry Number

Not Available

SMILES

CC=C(COC1OC(CO)C(O)C(O)C1O)C1=C(CO)C(=O)N2CCC3=C(NC4=CC=CC=C34)C2=C1

InChI Identifier

InChI=1S/C26H30N2O8/c1-2-13(12-35-26-24(33)23(32)22(31)20(11-30)36-26)16-9-19-21-15(14-5-3-4-6-18(14)27-21)7-8-28(19)25(34)17(16)10-29/h2-6,9,20,22-24,26-27,29-33H,7-8,10-12H2,1H3

InChI Key

XRSKCXMPZFQFCK-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
Nauclea officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
5-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Benzodioxole
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Aldehyde
Organooxygen compound
Organic oxide
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	1.11	ALOGPS
logP	-1.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.71 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.1 m³·mol⁻¹	ChemAxon
Polarizability	53.03 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one (NP0188494)

MOL for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

3D MOL for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

3D SDF for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

3D-SDF for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

PDB for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

3D PDB for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

SMILES for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

INCHI for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

Structure for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)

3D Structure for NP0188494 (3-(hydroxymethyl)-2-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-2-yl)-6h,7h,12h-indolo[2,3-a]quinolizin-4-one)