NP-MRD: Showing NP-Card for 14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one (NP0266463)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 10:48:53 UTC

Updated at

2022-09-08 10:48:54 UTC

NP-MRD ID

NP0266463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one

Description

14-{[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]Docosa-2,4,6,8(21),16-pentaen-22-one belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. 14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one is found in Stachys albens. Based on a literature review very few articles have been published on 14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]Docosa-2,4,6,8(21),16-pentaen-22-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082212482D          

 35 41  0  0  0  0            999 V2000
    1.2348   -0.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805   -0.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    0.0947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    1.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004    2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058    2.5934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    3.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    3.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876    4.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768    3.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150    4.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    3.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6042    3.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    2.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5278    2.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381    1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820    2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6152    2.4137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    2.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3037    1.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511    1.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.4305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1147   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414    0.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340    1.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    1.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    1.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  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
 24 32  1  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  0  0  0  0
 19 35  1  0  0  0  0
M  END

     RDKit          3D

 63 69  0  0  0  0  0  0  0  0999 V2000
   -3.2295    0.0271    2.5086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910   -0.4362    1.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257   -1.4167    1.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194   -1.0753    2.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -1.9229    2.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346   -2.0668    1.3284 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7335   -0.9412    0.9959 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099   -1.1239    0.9472 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6445   -0.3277    1.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    0.9983    1.8394 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0686    1.7817    2.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7825    3.1297    2.8520 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379    1.5976    0.4988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0873    2.8635    0.4250 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.6983   -0.6474 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6571    1.2109   -1.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534   -0.6782   -0.3247 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6358   -1.5719   -1.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -2.3949    0.2766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0675   -1.3872   -0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9936   -1.7958   -1.8973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020   -0.7823   -2.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516   -0.3633   -3.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0668    0.2259   -2.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988   -0.5973   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    0.0010    0.2028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    1.2048   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0501    2.2039    0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018    3.3621    0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839    3.5070   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0209    2.5116   -2.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5769    1.3696   -1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3240   -1.9509   -1.2869 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3256   -2.8810   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253   -2.5856    0.9027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9484   -0.2494    3.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933   -2.9417    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373   -2.1632    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1818    1.1465    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    1.3588    3.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510    1.6364    2.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285    3.6478    2.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612    1.6305    0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096    3.4455   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    0.6871   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939    0.6871   -2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373   -0.4627   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6462   -2.4838   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -3.3797   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126   -1.2905   -1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3465   -0.4216   -0.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -1.0985   -3.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6247    0.1405   -2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0737   -1.2408   -3.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    0.4164   -4.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0513    2.0619    1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    4.1894    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392    4.4200   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9831    2.5697   -3.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9834   -2.3539   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -2.9562    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022   -3.9164   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3158   -3.4734    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3 35  1  0
 35 34  1  0
 34 33  1  0
 33 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 26  2  1  0
  2  1  2  0
 21 20  1  0
 20 19  1  0
  8 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 10  1  0
 19  6  1  0
  2  3  1  0
 19 35  1  0
 25 33  1  0
 32 27  1  0
 32 24  1  0
 12 42  1  0
 11 40  1  0
 11 41  1  0
 10 39  1  1
  8 38  1  1
  6 37  1  1
  4 36  1  0
 35 63  1  1
 34 61  1  0
 34 62  1  0
 33 60  1  6
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 20 50  1  0
 20 51  1  0
 19 49  1  6
 17 47  1  1
 18 48  1  0
 15 45  1  6
 16 46  1  0
 13 43  1  1
 14 44  1  0
M  END


  Mrv1652309082212482D          

 35 41  0  0  0  0            999 V2000
    1.2348   -0.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805   -0.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    0.0947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    1.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004    2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058    2.5934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    3.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    3.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876    4.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768    3.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150    4.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    3.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6042    3.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    2.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5278    2.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381    1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820    2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6152    2.4137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    2.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3037    1.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511    1.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.4305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1147   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414    0.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340    1.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    1.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    1.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  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
 24 32  1  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=C3C4CC5N(CCC6=C5N(C5=CC=CC=C65)C3=O)CC24)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28N2O8/c28-9-18-20(29)21(30)22(31)25(34-18)35-24-14-8-26-6-5-12-11-3-1-2-4-16(11)27-19(12)17(26)7-13(14)15(10-33-24)23(27)32/h1-4,10,13-14,17-18,20-22,24-25,28-31H,5-9H2

> <INCHI_KEY>
BRAQZYMVVJYIJR-UHFFFAOYSA-N

> <FORMULA>
C25H28N2O8

> <MOLECULAR_WEIGHT>
484.505

> <EXACT_MASS>
484.18456587

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.769121755363926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{11,20}.0^{13,18}]docosa-2,4,6,8(21),16-pentaen-22-one

> <JCHEM_LOGP>
-0.7298090956666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198724738525527

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207031304257711

> <JCHEM_PKA_STRONGEST_BASIC>
6.160060370643884

> <JCHEM_POLAR_SURFACE_AREA>
133.85000000000002

> <JCHEM_REFRACTIVITY>
120.51149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{11,20}.0^{13,18}]docosa-2,4,6,8(21),16-pentaen-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       2.305  -1.716   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.959  -0.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.336   0.124   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.084  -0.580   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.479   0.177   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.482   1.764   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.850   2.472   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.921   4.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.624   4.841   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.695   6.379   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.399   7.210   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.470   8.749   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.063   7.087   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.135   8.625   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.360   6.256   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.728   6.963   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.289   4.718   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.585   3.887   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.191   2.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.526   4.233   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.148   4.506   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.461   5.430   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.978   4.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.300   3.302   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.082   2.380   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       3.275   0.804   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       4.867   0.742   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.814  -0.472   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.339  -0.259   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.917   1.168   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.970   2.382   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.445   2.169   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.828   3.190   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.840   2.337   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.126   1.571   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25    2   27                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24   27                                                  
CONECT   33   25   21   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    3   19                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈N₂O₈

Average Mass

484.5050 Da

Monoisotopic Mass

484.18457 Da

IUPAC Name

14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{11,20}.0^{13,18}]docosa-2,4,6,8(21),16-pentaen-22-one

Traditional Name

14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{11,20}.0^{13,18}]docosa-2,4,6,8(21),16-pentaen-22-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=C3C4CC5N(CCC6=C5N(C5=CC=CC=C65)C3=O)CC24)C(O)C(O)C1O

InChI Identifier

InChI=1S/C25H28N2O8/c28-9-18-20(29)21(30)22(31)25(34-18)35-24-14-8-26-6-5-12-11-3-1-2-4-16(11)27-19(12)17(26)7-13(14)15(10-33-24)23(27)32/h1-4,10,13-14,17-18,20-22,24-25,28-31H,5-9H2

InChI Key

BRAQZYMVVJYIJR-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
Stachys albens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

18-oxayohimban
Yohimbine alkaloid
Pyridoindole
Beta-carboline
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyrroloazepine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Azepine
Monosaccharide
Benzenoid
Oxane
Piperidine
Vinylogous ester
Pyrrole
Heteroaromatic compound
Lactam
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Acetal
Oxacycle
Polyol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.73	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	6.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.51 m³·mol⁻¹	ChemAxon
Polarizability	48.77 Å³	ChemAxon
Number of Rings	7	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

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

163187594

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one (NP0266463)

MOL for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

3D MOL for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

3D SDF for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

3D-SDF for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

PDB for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

3D PDB for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

SMILES for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

INCHI for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

Structure for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)

3D Structure for NP0266463 (14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-15-oxa-1,11-diazahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹¹,²⁰.0¹³,¹⁸]docosa-2,4,6,8(21),16-pentaen-22-one)