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Ketcher is a tool to draw molecular structures and chemical reactions.

Ketcher Overview

Ketcher is a tool to draw molecular structures and chemical reactions. The application operates in two modes - Standalone and Remote:

  • Standalone mode is based on WASM and can be run as client-only application without a backend.

  • Remote version requires Indigo Service as a backend server to perform complex calculations (When the server is not responding you can continue to work in the application although some of the functions will be unavailable).

Ketcher consists of the following elements:

Note : Depending on the screen size, some tools on the Tool palette can be displayed in expanded or collapsed forms.

Using the Tool palette, you can

  • draw and edit a molecule or reaction by clicking on and dragging atoms, bonds, and other elements provided with the buttons on the Atoms toolbar and Tool palette;

  • delete any element of the drawing (atom or bond) by clicking on it with the Erase tool;

  • delete the entire molecule or its fragment using the lasso, rectangle, or fragment selection and the Erase tool;

  • draw special structures (see the following sections);

  • select the entire molecule or its fragment in one of the following ways (click on the button align=center to see the list of available options):

To select one atom or bond, click Lasso (1) or Rectangle Selection tool (2), and then click the atom or bond.

To select the entire structure:

  • Select the Fragment Selection tool (3) and then click the object.

  • Select the Lasso or Rectangle Selection tool, and then drag the mouse to select the object.

-Ctrl-clickwith the Lasso or Rectangle Selection tool.

To select multiple atoms, bonds, structures, or other objects, do one of the following:

-Shift-clickwith the Lasso or Rectangle Selection tool selects some (connected or not) atoms/bonds.

  • With the Lasso or Rectangle Selection tool click and drag the mouse around the atoms, bonds, or structures that you want to select.

Note :Ctrl+Shift-click each structurewith the Lasso or Rectangle Selection tool selects several structures.

You can use the buttons of the Main toolbar:

  • Clear Canvas (1) button to start drawing a new molecule; this command clears the drawing area;

  • Open… (2) and Save As… (3) buttons to import a molecule from a molecular file or save it to a supported molecular file format;

  • Copy with additional abilties to Copy As (4), Paste (5), Cut (6) buttons to perform the corresponding actions;

  • Undo (7) / Redo (8) to manage the last actions taken on the canvas;

  • Aromatize (Alt+a) / Dearomatize (Ctrl+Alt+a) buttons to mark aromatic structures (to convert a structure to the Aromatic or Kekule presentation);

  • Layout button (11) to change the position of the structure to work with it with the most convenience;

  • Clean Up button (12) to improve the appearance of the structure by assigning them uniform bond lengths and angles.

  • Calculate CIP button (13) to determine R/S and E/Z configurations;

  • Check Structure button (Alt+s) to check the following properties of the structure. Check will be conducted immediately when the operation is selected. You can check only the Settings you are interested in and check structure again with new settings by clicking on Check button. Apply button will save the Settings checked and they will be applied for the file saving.

  • Calculated Values button (15) to display some properties of the structure:

  • 3D Viewer button (16) to open the structure in the three-dimensional

  • Settings button (17) to make some settings for molecular files:

  • Help button (18) to view Help;

  • About button (19) to display version and copyright information of the program.

  • Fullscreen mode button (20) allows to initiate displaying Ketcher window in the fullscreen mode.

  • Zoom panel (21) displays the current zoom percentage. Click to expand the Zoom panel and use the following actions: Zoom percentage (22) to set the view manually, Zoom in (23) / Zoom out (24) to scale the view gradually, Zoom 100% (25) to enable the default zoom setting.

3D Viewer

The structure appears in a modal window after clicking on the 3D Viewer button on the top panel:

You can perform the following actions:

  • Rotate the structure holding the left mouse button;

  • Zoom In/Out the structure;

Ketcher Settings allow to change the appearance of the structure and background coloring on the 3D Viewer tab.

"Lines" drawing method, "Bright" atom name coloring method and "Light" background coloring are default.

Drawing Atoms

To draw/edit atoms you can:

  • select an atom in the Atoms toolbar and click inside the drawing area;

  • if the desired atom is absent in the toolbar, click on the button to invoke the Periodic Table and click on the desired atom (available options: Single – selection of a single atom, List – choose an atom from the list of selected options (To allow one atom from a list of atoms of your choice at that position), Not List - exclude any atom on your list at that position).

  • add an atom to the existing molecule by selecting an atom in the Atoms toolbar, clicking on an atom in the molecule, and dragging the cursor; the atom will be added with a single bond; vacant valences will be filled with the corresponding number of hydrogen atoms;

  • change an atom by selecting an atom in the Atoms toolbar and clicking on the atom to be changed; in the case a wrong valence appears the atom will be underlined in red;

  • change an atom by clicking on an existing atom with the Selection tool and starting to enter text after that; type another atom symbol in the text box:

  • change the charge of an atom by selecting the Charge Plus or Charge Minus tool and clicking consecutively on an atom to increase/decrease its charge:

  • change an atom or its properties by double-clicking on the atom to invoke the Atom Properties dialog (the dialog also provides atom query features):

  • click on the button to use the Extended table and select a corresponding Generic group or Special Node:

Drawing Bonds

To draw/edit bonds you can:

  • Click an arrow on the Bond tool in the Tool palette to open the drop-down list with the following bond types:















  • select a bond type from the drop down list and click inside the drawing area; a bond of the selected type will be drawn;

  • click on an atom in the molecule; a bond of the selected type will be added to the atom at the angle of 120 degrees;

  • add a bond to the existing molecule by clicking on an atom in the molecule and dragging the cursor; in this case you can set the angle manually;

  • change the bond type by clicking on it;

  • use the Chain Tool to draw consecutive single bonds;

  • change a bond or its properties by double-clicking on the bond to invoke the Bond Properties dialog:

  • clicking on the drawn stereo and dative bonds change their direction.

  • clicking with the Single Bond tool or Chain tool switches the bond type cyclically: Single-Double-Triple-Single.

Drawing R-Groups

Use the R-Group toolbox to draw R-groups in Markush structures:

Selecting the R-Group Label Tool (1) and clicking on an atom in the structure invokes the dialog to select the R-Group label for a current atom position in the structure:

Selecting the R-Group label and clicking OK converts the structure into a Markush structure with the selected R-Group label:

Note : You can choose several R-Group labels simultaneously:

Particular chemical fragments that may be substituted for a given R-Group form a set of R-Group members. R-Group members can be any structural fragment, including functional groups and single atoms or atom lists.

To create a set of R-Group members:

  1. Draw a structure to become an R-Group member.

  2. Select the structure using the R-Group Fragment Tool (2) to invoke the R-Group dialog; in this dialog select the label of the R-Group to assign the fragment to.

  3. Click on Apply to convert the structure into an R-Group member.

An R-Group attachment point is the atom in an R-Group member fragment that attaches the fragment to the initial Markush structure.

Selecting the Attachment Point Tool (3) and clicking on an atom in the R-Group fragment converts this atom into an attachment point. If the R-Group contains more than one attachment point, you can specify one of them as primary and the other as secondary. You can select between either the primary or secondary attachment point using the dialog that appears after clicking on the atom:

If there are two attachment points on an R-Group member, there must be two corresponding attachments (bonds) to the R-Group atom that has the same R-Group label. Clicking on Apply in the above dialog creates the attachment point.

Schematically, the entire process of the R-Group member creation can be presented as:

R-Group Logic

Ketcher enables one to add logic when using R-Groups. To access the R-Group logic:

  1. Create an R-Group member fragment as described above.

  2. Move the cursor over the entire fragment for the green frame to appear, then click inside the fragment. The following dialog appears:

  3. Specify Occurrence to define how many of an R-Group occurs. If an R-Group atom appears several times in the initial structure, you will specify Occurrence">n", n being the number of occurrences; if it appears once, you see "R1 > 0".

  4. Specify H at unoccupied R-Group sites ( RestH ): check or clear the checkbox.

  5. Specify the logical Condition. Use the R-Group condition If R(i) Then to specify whether the presence of an R-Group is dependent on the presence of another R-Group.

Marking S-Groups

To mark S-Groups, use the S-Group tool and the following dialog that appears after selecting a fragment with this tool:

Available S-Group types:

Generic

Generic is a pair of brackets without any labels.

Multiple group

A Multiple group indicates a number of replications of a fragment or a part of a structure in contracted form.

SRU Polymer

The Structural Repeating Unit (SRU) brackets enclose the structural repeating of a polymer. You have three available patterns: head-to-tail (the default), head-to-head, and either/unknown.

Superatom

An abbreviated structure (abbreviation) is all or part of a structure (molecule or reaction component) that has been abbreviated to a text label. Structures that you abbreviate keep their chemical significance, but their underlying structure is hidden. The current version can't display contracted structures but correctly saves/reads them into/from files.

Data S-Groups

The Data S-Groups Tool is a separate tool for comfortable use with the accustomed set of descriptors (like Attached Data in Marvin Editor).

You can attach data to an atom, a fragment, a multifragment, a single bond, or a group. The defined set of Names and Values is introduced for each type of selected elements:

  • Select the appropriate S-Group Field Name.

  • Select the appropriate Field Value.

  • Labels can be specified as Absolute, Relative or Attached.

Changing Structure Display

Use the Rotate tool to change the structure display:

Rotate Tool (1) Erase (Del) (4)

This tool allows rotating objects.

  • If some objects are selected, the tool rotates the selected objects.
  • If no objects are selected, or all objects are selected, the tool rotates the whole canvas
  • The default rotation step is 15 degrees.
  • Press and hold the Ctrl key for more gradual continuous rotation with 1 degree rotation step

Select any bond on the structure and click Alt+H to rotate the structure so that the selected bond is placed horizontally. Select any bond on the structure and click Alt+V to rotate the structure so that the selected bond is placed vertically.

Flip Tool (2, 3)

This tool flips the objects horizontally or vertically.

  • If some objects are selected, the Horizontal Flip tool (or Alt+H) flips the selected objects horizontally
  • If no objects are selected, or all objects are selected, the Horizontal Flip tool (or Alt+H) flips each structure horizontally
  • If some objects are selected, the Vertical Flip tool (or Alt+V) flips the selected objects vertically
  • If no objects are selected, or all objects are selected, the Vertical Flip tool (or Alt+V) flips each structure vertically

Drawing Reactions

To draw/edit reactions you can:

  • draw reagents and products as described above;
  • use options of the Reaction Arrow Tool to draw an arrow. Select the arrow needed from the list
  • draw pluses in the reaction equation using the Reaction Plus Tool
  • map same atoms in reagents and products with the Reaction Mapping Tools . Explore the available reaction mapping tools below:

.

1 – Reaction Auto-Mapping Tool

2 – Reaction Mapping Tool

3 – Reaction Unmapping Tool

Drawing graphical objects

To draw graphical objects click the arrow on the Shape Ellipse tool in the Tools palette to open the drop-down list with the following tools:

.

Shape Ellipse (1), Shape Rectangle (2), and Shape Line (3).

Creating text objects on the canvas

To add text to the canvas click the Add text tool in the Tools palette and click the canvas to open the Text editor window:

  • To enter text, type in the Text editor field.
  • To edit text, double click the text object on the canvas.
  • Change the text style to bold and italic, make it subscript and superscript while typing or by selecting text and applying styles.

Templates toolbar

You can add templates (rings or other predefined structures) to the structure using the Templates toolbar together with the Custom Templates button located at the bottom:



To add a ring to the molecule, select a ring from the toolbar and click inside the drawing area, or click on an atom or a bond in the molecule.

Rules of using templates:

  • Selecting a template and clicking on an atom in the existing structure adds the template to the structure connected with a single bond:

  • Selecting a template and dragging the cursor from an atom in the existing structure adds the template directly to this atom resulting in the fused structure:

  • Dragging the cursor from an atom in the existing structure results in the single bond attachment if the cursor is dragged to more than the bond length; otherwise the fused structure is drawn.

  • Selecting a template and clicking on a bond in the existing structure created a bond-to-bond fused structure:

  • The bond in the initial structure is replaced with the bond in the template.

  • This procedure doesn't change the length of the bond in the initial structure.

  • Dragging the cursor relative to the initial bond applies the template at the corresponding side of the bond.

Note : The added template will be fused by the default attachment atom or bond preset in the program.

Note : User is able to define the attachment atom and bond by clicking the Edit button for template structure in the Template Library.

The Custom Templates button allows to view the list of templates available; both built-in and created by user:

To create a user template:

  • draw a structure.

  • click the Save as button.

  • click the Save to Templates button. Template edit form will be displayed

  • enter a name and define the attachment atom and bond by clicking on the structure preview. Click on Apply button to save the template.

Saved template will be available in User Templates tab in the list of templates.

Functional Groups

Ketcher allows you to select and use Functional Groups to properly represent your structure on the canvas. Set of functional groups available is predefined and can't be changed right now.

Explore the list of the Functional Groups available in the Templates library. Open it using the icon in the bottom toolbar:

Navigate to the Functional Groups tab to explore the FGs available:

Filter Functional Groups by name:

To add Functional Group to the canvas and join it to the structure do the following:

  1. Select the proper FG in the FG menu and click Add to canvas
  2. Click on the atom FG should connect with on the canvas: bond will be created automatically and FG will be joined to the structure.

You can just click on the canvas having the FG selected. To connect it with other structure on the canvas do the following:

  1. Select Simple Bond tool in the left Ketcher toolbar
  2. Drag bond from the connection atom and drop it to the Functional Group on the canvas.

Functional Group on the canvas can be Expanded to view it's internal structure. Expanded group can be Contracted back to the compact presentation.

You can also Remove the Abbreviation on the group - it will allows you to work with the functional group atoms and bonds as with regular atoms and bonds on the canvas. To Expand, Contract and Remove Abbreviation:

  1. Click on the FG with right mouse button:
  2. Select the command from the context menu

Please, note that a lot of Ketcher tools will be not applicable for the separate atoms and bonds of FG. FG can only be selected as a whole. It can also be deleted, moved, or rotated only as an entire entity.

Ketcher will let you know if the tool is not applicable for the FG and will suggest to Remove the Abbreviation immediately:

Aromatize & Dearomatize operations will not be applied to the rings that are part of the FG.

Functional Groups will be considered as super atoms when opening and saving .mol files.

Working with Files

Ketcher supports the following molecular formats that can be entered either manually or from files:

You can use the Open… and Save As… buttons of the Main toolbar to import a molecule from a molecular file or save it to a supported molecular file format.

The Open Structure dialog enables one to either browse for a file or manually input, e.g. the Molfile ctable for the molecule to be imported:

The text editor form is initiated for the text from the Clipboard and when the file is selected for opening. It allows to immediately edit the text representation before opening the structure:

Ketcher suggests 2 ways for structure to be opened:

Open as New Project will clear the canvas and position new structure on it. Add to Canvas will save the structure in the clipboard. Click on the canvas to place it.

The Save Structure dialog enables one to save the molecular file:

Select the format needed in the File Format drop down.
Check out the Warnings tab if it's represented. It provides the list of chemical information that can't be saved properly to the format selected.

You can save a structure as image (in Standalone mode and in Remote mode when the server is available) by selectinig the SVG Document or PNG Image format. Please, note that saving structure to the image formats will results in chemical information loss in the file. You will not be able to open files in these formats in Ketcher. Supported graphics file formats are: Portable Network Graphics (.png) and Scalable Vector Graphics (.svg).

Stereochemistry

When the structure with the correct tetrahedral stereochemistry is created on the canvas you can open the ‘Enhanced Stereochemistry’ window by clicking the Stereochemistry button and assign stereo marks:

In the Stereochemistry tab in Settings you can:

  • enable/disable display of the Stereo flags
  • set the text of the Absolute/AND/OR/Mixed flags
  • change the style of the Label display at stereogenic centers
  • select the color of Absolute/AND/OR stereogenic centers
  • choose one of the four color display modes
  • enable/disable option when Chiral flag is ignored (false by default)

When option Ignore the chiral flag is true it will affect opening and saving of MDL V2000 and MDL V3000 files, as well as the display of labels at stereogenic centers and stereo flags:

  • stereo flags are not displayed

  • labels at stereogenic centers are displayed only for non-absolute groups

  • MDL V2000 and MDL V3000 file formats will save stereo information according to the following table

This parameter can be changed via ketcher.setSettings() api, e.g. ketcher.setSettings({ ignoreChiralFlag: true })

Hotkeys

You can use keyboard hotkeys (including Numeric keypad) for some features/commands of the Editor. To display the hotkeys just place the cursor over a toolbar button. If a hotkey is available for the button, it will appear in brackets after the description of the button.

NOTE: Mod key is Command on OSX and Ctrl on PC systems

General

Shortcut Action
Mod+Delete Clear Canvas
Mod+o Open…
Mod+s Save As…
Mod+z Undo
Mod+Shift+z, Mod+y Redo
Mod+x Cut
Mod+c Copy
Mod+Shift+f Copy Image
Mod+m Copy as MOL
Mod+Shift+k Copy as KET
Mod+v Paste
Mod+a Select All
Mod+Shift+a Deselect All
Mod+d Select descriptors

Server

Shortcut Action
Alt+a Aromatize
Ctrl+Alt+a Dearomatize
Mod+l Layout
Mod+Shift+l Clean Up
Mod+p Calculate CIP
Alt+s Check structure
Alt+c Calculate values

Debug

Shortcut Action
Mod+Shift+r force-update
Alt+Shift+r qs-serialize

Tools

Shortcut Action
Mod+h Hand tool
Escape Rotate between: Lasso Selection, Rectangle Selection, Fragment Selection
Delete, Backspace Erase
Alt+e Stereochemistry
+ Charge Plus
- Charge Minus
Alt+r Rotate Tool
Alt+h Horizontal Flip
Alt+v Vertical Flip
Mod+g Rotate between: S-Group, Data S-Group
Mod+r Rotate between: R-Group Label Tool, Attachment Point Tool
Mod+Shift+r, Mod+r R-Group Fragment Tool
1 Rotate between: Single Bond, Single Up Bond, Single Down Bond, Single Up/Down Bond
2 Rotate between: Double Bond, Double Cis/Trans Bond
3 Triple Bond
4 Aromatic Bond
0 Any Bond
Alt+t Add text

Atoms

Shortcut Action
h Atom H
c Atom C
n Atom N
o Atom O
s Atom S
p Atom P
f Atom F
b Atom Br
i Atom I
k Atom K
Shift+c Atom Cl
Shift+s Atom Si
Shift+n Atom Na
Shift+b Atom B
r Pseudoatom
d Deuterium
a Any atom
q Any heteroatom
m Any metal
x Any halogen
/ Display the Atom Properties dialog box

Bonds

Shortcut Action
/ Open bond properties

Zoom

Shortcut Action
Mod+_, Mod+- Zoom Out
Mod+=, Mod++ Zoom In
Mod+Shift+0 Zoom 100%

Templates

Shortcut Action
Shift+t Structure Library
t Rotate between: Benzene, Cyclopentadiene, Cyclohexane, Cyclopentane, Cyclopropane, Cyclobutane, Cycloheptane, Cyclooctane

FunctionalGroups

Shortcut Action
Shift+f Functional Groups

Help

Shortcut Action
?, &, Shift+/ Help

Note : Please, useCtrl+Vto paste the selected object in Google Chrome and Mozilla Firefox browsers.