Instruction to search natural compounds on CH-NMR-NP
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Compound Search
Here is the initial page for database search.

The Name (compound name)、Atoms and Molecular Formula、MolecularWeight、13C Chemical Shift、1H Chemical Shift、No Signal Region、PartialStructure、classification number（NP No.）can be used as query items. Eachitem is used as a logical AND operator. 1H chemical shift search can be used
when the Enable Detailed Search check box was clicked.

Name

A compound name is used as a query. The compound name is usually a trivial
name, which is described in the original paper, but some of them may be achemical name (IUPAC Name, etc.). A search word is a partial match retrieval,but ‘*’ or ‘!’ can be used as wildcard character. A ‘*’ matches any number ofcharacter, and a ‘!’ matches only one character. When using wildcard
character, a search word will be a exact word.
Atoms

The number of atoms of carbon, hydrogen, nitrogen and oxygen are used as aquery. The other element should be set in the ‘Molecular Formula’ form. A
atom number can be specified as a range. For example, ’21-23’ at ‘C’ searches
compounds that have carbons from 21 to 23. The ‘-21’ at ‘C’ searches
compounds have not exceeding 21 carbons. The ’23-‘ at ‘C’ searches
compounds that have more than 23 carbons. The ‘0’ searches compounds that
contain none of specified element.
Molecular Formula

A molecular formula is used as a query. It is case insensitive, and an order ofelements has no limitation. The range specification cannot be used, but ‘0’searches compounds that contain none of specified element. For example,‘C15H18BrS2’ and ‘BrS2c15h18’ find same compounds.

Molecular Weight

A molecular weight is used as a query. The value can be range specified. The
value in the database is rounded.
13C Chemical Shift

A 13C chemical shift (ppm unit) is used as a query. The multiple chemicalshifts can be set by comma-delimited format. An allowance is applied to all
chemical shifts. All chemical shifts are used as logical AND operators,
however, similarity can loosen search condition. For example, 3 chemical
shifts with 70% similarity searches compounds have 2 of 3 specified chemicalshifts.
The ‘From File’ button can be used for setting chemical shifts list. The
chemical shifts list is automatically set, when a “peak picked carbon spectrum”
is specified. A specified file must be a .jdf file (Delta NMR software format).
The solvent peak markers are recommended to be eliminated before
uploading because database does not include solvent peaks.

When using the ‘Enable Detailed Search’, the number of bonded 1H atoms(multiplicity of carbon) can be specified. For example, the ‘3’ should bespecified in this field, if the searching 13C chemical shift is CH3. Commadelimited specification can be used to specify this for multiple carbon signals.
When the multiplicities of some carbons are unclear, those carbons should beallocated at the back. For example, if the 13C chemical shifts are ’40, 41, 71’
and these multiplicities are ‘CH3, CH2, unclear’, this field should be ‘3, 2’.
When the ‘Search bonded 1H chemical shift(s)’ is on, it searches compounds
that have specified 13C bonding to specified 1H. A manner of array in the fields
is same as ‘number of bonded 1H atoms’, but if 1H of CH2 are non-equivalent,
two same 13C chemical shifts should be specified. For example, to searchcompounds that have 13C at 72 ppm is bonded to 1H at 3.9 ppm and 4.4 ppm,
put ’72,72’ in 13C chemical shift field and ‘7.9, 4.4’ in 1H chemical shift field.
Please note that there are a lot of compounds that have not enough 1Hchemical shift information in the database.
13C No Signal Region

A no signal region of 13C chemical shift (ppm unit) is used as a query.

Structure Search

A partial structure is used as a query. The JavaScript ‘JSME Molecular
Editor’ and ‘RDKit cartridge’ are used for structure drawing and structure
search respectively.
NP No.

A classification number（NP No.）is used as a query. NP No. can be range
specified.

1H Chemical Shift (w/ Enable Detailed Search)

A 1H chemical shift (ppm unit) is used as a query. The multiple chemical shifts
can be set by comma-delimited format. An allowance is applied to all chemicalshifts. All chemical shifts are used as logical AND operators, however,similarity can loosen search condition. For example, 3 chemical shifts with
70% similarity searches compounds have 2 of 3 specified chemical shifts.
The ‘From File’ button can be used for setting chemical shifts list. The
chemical shifts list is automatically set, when a “peak picked proton spectrum”
is specified. A specified file must be a .jdf file (Delta NMR software format).
*Please note that proton J-splitting are not considered and there are a lot ofcompound that have not enough 1H chemical shift information.
1H No Signal Region (w/ Enable Detailed Search)

A no signal region of 1H chemical shift (ppm unit) is used as a query.
Sort

Search result is sorted in descending order of carbon number as a default.
The compounds of same carbon number are sorted in descending of numberof hydrogen, nitrogen, oxygen, in that order. The NP No., compound name(alphabetical), number of atoms (CHNO), molecular weight, similarity can beused for sorting in ascending or descending order.

Search Result

In the search result list, the compound name, structure, NP No., molecular
formula, and solvent are displayed for each compounds. When clicking thecompound name or structure, detailed data will be displayed on a newwindow.

Detailed data display

Print Layout display

Paging

In a detailed data page, a chemical structure (w/ assignment number),compound information, an assignment List and a 13C NMR spectrum areshown as a default. The paging buttons (it follows sorting in search results)
located at the page bottom.

・ Chemical Structure
a chemical structure is corresponding to the original paper. All carbons
are numbered for spectrum assignment. Abbreviated partial structure
e.g. Acetyl, Benzyl, Glu are transcribed into full structure. The carbon
number is corresponding to the original paper, but non-number e.g.
alpha, beta, 1’, 1”, etc. were replaced into numeric character. A
duplicative number is not used for one-to-one assignment to chemical
shifts. The equivalent carbons are not numbered.

・ Compound Information➢Name (trivial name or chemical name in the original paper)
Special character including Greek alphabet are replaced intoalphameric character. Superscript, subscript, arrows are alsoreplaced. A long authoritative chemical name might be described if
it is only written in the paper.

➢Molecular Formula
Molecular formula formed based on the chemical structure.

➢

Molecular Weight
Molecular formula weight based on the chemical structure. The
value after the decimal point might be different from originalpaper. This is explained as resulting from diverseness of naturalabundance at production area.

➢NP No.
A classification number for each compound.

➢Spectral Key
Corresponding to spectrum (13C NMR and 1H NMR)➢Source
The feed material for the extraction of natural product. Described
as an academic name in usual case.

➢Remarks
A brief comment (plant, fish, shellfish, fungus, etc.) about
extraction feed.

➢Characteristic
The characterization described by author of original paper.

➢Chemical Name
An authoritative chemical name as represented by IUPAC name if
it is described in the original paper.

➢CAS Registry No.

➢Solvent
The solvent for NMR experiment, and measurement condition(temperature, pH, etc.) are described. The most of them are 2535 °C is assumed if temperature is not specified.

➢1H Frequency

An observing frequency of the 1H NMR (magnetic field of NMRmachine). The maximum frequency in the experimental section isused if it is not described for individual data.
➢Shift Ref.
A chemical shift reference of NMR spectra. For example, in case ofCDCl3, the description ‘7.25 / 77.0’ means that 1H signal of residual
CHCl3 was set to 7.25 ppm and 13C signal of CDCl3 was set to 77.0
ppm as according to the paper.

➢Reference
An original paper of corresponding data. It is described with firstauthor only. The URL link target is a result of google scholar
search.
In case of the 6,000 compounds from SDBS-NMR, reference shows
SDBS registry number.

➢Comments
A comment by database editor.

・ Assignment List
Numbering of each 13C, chemical shift of 13C, carbon type (CH3, CH2, CH,C), chemical shift of bonded 1H, comment including J coupling pattern of1H and J value etc. are described. When using 13C Chemical shift queryat the compound search, matched 13C were highlighted. 1H chemical shift

on the row without 13C number shows 2nd chemical shift of nonequivalent 1H or OH/NH. In case of OH/NH, it is specified in commentfield.
・ Show 13C NMR Spectrum (checkbox)
The ON shows 13C NMR spectrum, and OFF hides it. Show/Hide state isreflected on the print layout page.
・ 13C NMR Spectrum
The virtual 13C NMR spectrum with assignment carbon number isshown. When using 13C Chemical shift query at the compound search,matched 13C were highlighted. The intensity of individual peakcorrespond to the number of carbon. The display range of spectrum canbe expanded by drag & drop operation or numerical entry. Click resetbutton to reset view.
The checkboxes at the bottom (C, CH, CH2, CH3) switches Show/Hidecorresponding peaks. The APT checkbox switches spectrum to up (CH3,CH) and down (CH2, C) view. The ‘Show 1H NMR Shifts’ checkbox shows
1H chemical shift graph.

➢「Download 13C NMR data in Delta format」
Delta format 13C NMR spectrum data can be downloaded byclicking this link. The downloaded data can be opened by Delta
software, and it is easy to compare with measured NMR spectra.

・ 1H NMR Shifts
The 1H chemical shifts graph is shown. It is only a isotropic chemicalshift, and J splitting pattern is not shown.

・ View 1H and 13C Spectra
In case of the 6,000 compounds from SDBS-NMR, measured spectra canbe shown.

・ Print Layout
The print layout without unnecessary information e.g. header/footer,
URL links, buttons is shown in a new window. The ON/OFF states ofspectra are reflected on a print layout.

・ Paging
The paging of search result can be done by clicking paging buttons at thepage bottom. The page is corresponding to the sorting number of searchresult.

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