NP-MRD: Showing NP-Card for (1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid (NP0214634)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 13:59:25 UTC

Updated at

2022-09-05 13:59:25 UTC

NP-MRD ID

NP0214634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid

Description

(1S,2R,6E,7S,8R,9S,10S)-6-ethylidene-9,13,16-trihydroxy-11,20-dimethyl-8-(propan-2-yl)-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]Icosa-12,14,16-triene-2-carboxylic acid belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. (1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid is found in Hunteria umbellata. Based on a literature review very few articles have been published on (1S,2R,6E,7S,8R,9S,10S)-6-ethylidene-9,13,16-trihydroxy-11,20-dimethyl-8-(propan-2-yl)-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]Icosa-12,14,16-triene-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215592D          

 33 37  0  0  1  0            999 V2000
    4.3839    3.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    2.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0161    1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787    0.8366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064    1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8341    1.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100    1.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    0.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    2.4644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9742    3.2783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6116    3.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768    4.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070    4.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    3.6390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0671    4.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645    3.0448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2969    3.4245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    4.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9669    1.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465    0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    0.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238    1.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160    2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034    2.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794    2.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    3.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3690    3.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11  3  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 18 23  1  0  0  0  0
  7 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
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 67 71  0  0  0  0  0  0  0  0999 V2000
   -2.5273    2.7582   -1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    2.4462    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3098    1.4884    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886    1.3062    2.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    1.4535    3.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5185    1.7170    2.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219    0.4715    1.4553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6641   -0.5911    2.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765   -1.5705    2.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611   -0.5745    3.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    0.6221    0.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4010   -0.5860   -0.5021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4334   -0.5753   -1.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -1.9314   -2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966   -0.4520   -0.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022   -0.8920   -1.0735 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0125   -1.8357   -2.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9861   -1.0805    0.0128 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8904   -2.0971    0.9196 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981   -3.4355    0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076   -1.8994    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973   -0.4051    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    0.1769    0.9178 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8939    1.0531    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    2.4055    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    3.2015    0.9700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9642    3.0169   -0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326    2.2837   -1.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    0.9036   -1.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1687    0.2401   -2.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920    0.3010   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3068   -1.0827   -0.6536 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149   -2.1770   -1.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501    2.4312   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820    3.8802   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961    2.3276   -1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6653    3.0350    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5078    2.0971    2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2945    0.3581    2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507    2.5664    1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    1.9825    2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913    0.2387    4.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5745    1.3195   -0.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6322   -1.5434    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3184    0.1408   -2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352   -2.7726   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5342   -2.0533   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285   -1.8891   -3.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863   -0.5417    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3854    0.4244   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829   -1.3171   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    0.0782   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -1.7200   -2.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -3.7599    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3904   -4.1851    1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265   -3.5467   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   -2.3775    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948   -2.3553    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915   -0.1084    3.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687   -0.1131    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805    4.1993    1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    4.0993   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3178    2.7318   -2.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1613   -0.7142   -2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337   -2.4567   -2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2013   -1.9772   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8699   -3.1383   -0.5231 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 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  1
 19 20  1  0
 19 21  1  0
 21 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
  7  8  1  1
  8 10  1  0
  8  9  2  0
 11  3  1  0
 23 18  1  0
 31 24  1  0
 23  7  1  0
 32 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  4 38  1  0
  4 39  1  0
  6 40  1  0
  6 41  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  6
 17 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 26 61  1  0
 27 62  1  0
 28 63  1  0
 30 64  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
 10 42  1  0
M  END


  Mrv1652309052215592D          

 33 37  0  0  1  0            999 V2000
    4.3839    3.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    2.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0161    1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787    0.8366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064    1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8341    1.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100    1.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    0.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    2.4644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9742    3.2783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6116    3.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768    4.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070    4.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    3.6390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0671    4.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645    3.0448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2969    3.4245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    4.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9669    1.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465    0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    0.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238    1.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160    2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034    2.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794    2.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    3.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3690    3.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11  3  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 18 23  1  0  0  0  0
  7 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
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\COC[C@]2([C@H]1[C@@H](C(C)C)[C@H](O)[C@]13N(C)CC[C@]21C1=C(O)C=CC(O)=C1N3C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34N2O6/c1-6-14-11-33-12-23(22(31)32)18(14)17(13(2)3)21(30)25-24(23,9-10-26(25)4)19-15(28)7-8-16(29)20(19)27(25)5/h6-8,13,17-18,21,28-30H,9-12H2,1-5H3,(H,31,32)/b14-6-/t17-,18-,21+,23+,24+,25-/m1/s1

> <INCHI_KEY>
GZCHFHNDJQALPF-MOIZRIIWSA-N

> <FORMULA>
C25H34N2O6

> <MOLECULAR_WEIGHT>
458.555

> <EXACT_MASS>
458.241686823

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.576696206445334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,6E,7S,8R,9S,10S)-6-ethylidene-9,13,16-trihydroxy-11,20-dimethyl-8-(propan-2-yl)-4-oxa-11,20-diazapentacyclo[8.7.3.0^{1,10}.0^{2,7}.0^{12,17}]icosa-12,14,16-triene-2-carboxylic acid

> <JCHEM_LOGP>
0.1717576214950579

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.806371444642553

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7135057793583135

> <JCHEM_PKA_STRONGEST_BASIC>
6.705944311432718

> <JCHEM_POLAR_SURFACE_AREA>
113.7

> <JCHEM_REFRACTIVITY>
124.74389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6E,7S,8R,9S,10S)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0^{1,10}.0^{2,7}.0^{12,17}]icosa-12,14,16-triene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.183   6.555   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.435   5.036   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.245   4.059   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.497   2.539   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.307   1.562   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.865   2.103   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.548   3.415   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.424   2.645   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.885   2.715   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.675   1.126   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.804   4.600   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.552   6.120   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.742   7.097   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.490   8.616   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.226   7.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.695   6.793   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.859   8.181   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.920   5.684   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.287   6.392   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.977   7.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.384   5.311   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.695   3.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.172   4.164   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.805   3.455   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.417   1.965   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.513   0.884   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.068   1.556   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.164   2.637   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.776   4.128   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.873   5.209   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.708   4.537   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       1.398   5.914   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       0.689   7.281   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11   23                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7    3   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23   32                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18    7   24                                             
CONECT   24   23   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31   18   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,6E,7S,8R,9S,10S)-6-Ethylidene-9,13,16-trihydroxy-11,20-dimethyl-8-(propan-2-yl)-4-oxa-11,20-diazapentacyclo[8.7.3.0,.0,.0,]icosa-12,14,16-triene-2-carboxylate	Generator

Chemical Formula

C₂₅H₃₄N₂O₆

Average Mass

458.5550 Da

Monoisotopic Mass

458.24169 Da

IUPAC Name

(1S,2R,6E,7S,8R,9S,10S)-6-ethylidene-9,13,16-trihydroxy-11,20-dimethyl-8-(propan-2-yl)-4-oxa-11,20-diazapentacyclo[8.7.3.0^{1,10}.0^{2,7}.0^{12,17}]icosa-12,14,16-triene-2-carboxylic acid

Traditional Name

(1S,2R,6E,7S,8R,9S,10S)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0^{1,10}.0^{2,7}.0^{12,17}]icosa-12,14,16-triene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C\C=C1\COC[C@]2([C@H]1[C@@H](C(C)C)[C@H](O)[C@]13N(C)CC[C@]21C1=C(O)C=CC(O)=C1N3C)C(O)=O

InChI Identifier

InChI=1S/C25H34N2O6/c1-6-14-11-33-12-23(22(31)32)18(14)17(13(2)3)21(30)25-24(23,9-10-26(25)4)19-15(28)7-8-16(29)20(19)27(25)5/h6-8,13,17-18,21,28-30H,9-12H2,1-5H3,(H,31,32)/b14-6-/t17-,18-,21+,23+,24+,25-/m1/s1

InChI Key

GZCHFHNDJQALPF-MOIZRIIWSA-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
Hunteria umbellata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Pseudophrynamine skeleton
Carbazole
Pyrroloindole
Indole
Indole or derivatives
Alkaloid or derivatives
Dialkylarylamine
1-hydroxy-2-unsubstituted benzenoid
Oxane
N-alkylpyrrolidine
Benzenoid
Cyclic alcohol
Pyrrole
Pyrrolidine
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Azacycle
Polyol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Alcohol
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	0.17	ChemAxon
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	6.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	113.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	124.74 m³·mol⁻¹	ChemAxon
Polarizability	47.58 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163186404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid (NP0214634)

MOL for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

3D MOL for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

3D SDF for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

3D-SDF for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

PDB for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

3D PDB for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

SMILES for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

INCHI for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

Structure for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)

3D Structure for NP0214634 ((1s,2r,6e,7s,8r,9s,10s)-6-ethylidene-9,13,16-trihydroxy-8-isopropyl-11,20-dimethyl-4-oxa-11,20-diazapentacyclo[8.7.3.0¹,¹⁰.0²,⁷.0¹²,¹⁷]icosa-12,14,16-triene-2-carboxylic acid)