Shorthand notation for Sterols (ST)

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= Examples  =
= Examples  =
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{| class="wikitable" style="text-align: center"
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|-
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! scope="col" | Bond type<br>
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! scope="col" | Lipid class level mass$<br>
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! scope="col" | Lipid species level§<br>
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! scope="col" | Bond type level<br>
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! scope="col" | LIPID MAPS Structure level <br>
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|-
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|-
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| Cholesterol <br>
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| ST (386)<br>
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| ST 27:1_OH <br>
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| ST 27:1_OH<br>
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| ST 27:1/OH [5Z,3βOH ]<br>
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|-
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| 3β-Hydroxycholestenoic acid<br>
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| ST (416)<br>
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| ST A27:1_OH <br>
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| ST A27:1_OH<br>
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| ST A27:1/OH [5Z,3βOH,25(R),26CO2H]<br>
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|-
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| Lithocholic acid <br>
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| ST (376)<br>
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| ST A24_OH<br>
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| ST A24_OH<br>
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| ST A24/OH [5βH,3αOH,24CO2H]<br>
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|-
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| Progesterone<br>
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| ST (314)<br>
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| ST 21:3_OH2<br>
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| ST 21:1_O2<br>
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| ST 21:1/O2 [4Z,3O,20O]<br>
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|-
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| Testosterone<br>
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| ST (288)<br>
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| ST 19:2_OH2<br>
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| ST 19:1 _OH_O<br>
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| ST 19:1/OH/O [4Z,17βOH,3O]<br>
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|-
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| Dehydroepiandrosterone<br>
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| ST (288)<br>
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| ST 19:2_OH2<br>
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| ST 19:1_OH_O<br>
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| ST 19:1/OH/O [5Z,3βOH,17O]<br>
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|-
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| 17β-Estradiol<br>
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| ST (272)<br>
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| ST 18:3_OH2<br>
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| ST 18:3_OH2<br>
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| ST 18:3/OH2 [1Z,3E,5E,3OH,17βOH]<br>
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|-
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| Taurocholic acid<br>
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| ST (515)<br>
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| ST A24_OH3_T<br>
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| ST A24_OH3_T<br>
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| ST A24/OH3/T [5βH, 3αOH,7αOH,12αOH,24T]<br>
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|-
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| Glycochenodeoxycholic acid<br>
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| ST (449)<br>
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| ST A24_OH2_G<br>
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| ST A24_OH2_G<br>
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| ST A24/OH2/G [5βH, 3αOH,7αOH,24G]<br>
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|-
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| Dehydroepiandrosterone sulfate<br>
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| ST (368)<br>
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| ST 19:2_OH2_S<br>
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| ST 19:1_OH_O_S<br>
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| ST 19:1/OH/O/S [5Z,3βOH,17O,3S]<br>
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|-
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| 24(S)-Hydroxycholesterol 3-sulfate, 24-glucuronide<br>
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| ST (658)<br>
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| ST 27:1_OH2_S_GlcA<br>
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| ST 27:1_OH2_S_GlcA<br>
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| ST 27:1/OH2/S/GlcA [5Z,3βOH,24(S)OH,3S,24GlcA]<br>
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|-
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| Cholesteryl palmitate<br>
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| ST (624)<br>
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| SE 27:1/16:0<br>
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| SE 27:1/16:0<br>
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| CE 16:0<br>
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|-
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| Cholesteryl linoleate<br>
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| ST (648)<br>
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| SE 27:1/18:2<br>
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| SE 27:1/18:2<br>
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| CE 18:2(9Z,12Z)<br>
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|-
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| Zymosteryl oleate<br>
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| ST (648)<br>
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| SE 27:2/18:1<br>
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| SE 27:2/18:1<br>
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| SE 27:2 [5α,8E,24,3βFA]/18:1(9Z)<br>
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|}
$ m is the uncharged molecular mass<br>  
$ m is the uncharged molecular mass<br>  
[[Category:Nomenclature]]
[[Category:Nomenclature]]

Current revision

Rules for the annotation

  • Shorthand notation: ST number of carbon atoms:number of double bonds.
  • Annotation at the lipid species level is based on natural sterols possessing 18, 19, 21, 24, or 27 carbons and at least one hydroxyl group at position 3.
  • Functional groups, including all hydroxyl groups, are shown after the number of double bonds separated by an underscore and followed by the number of groups if more than one.
  • Proven positions of functional groups are shown after the number of double bonds separated by a slash. Specific stereochemistry of functional groups is shown in square brackets, (R) and (S) configurations are preferred for side-chain stereochemistry and are given in italics in parenthesis.
  • In the case of fully proven structures of cholesterol and cholesteryl esters abbreviations FC and CE, respectively can be used. CE is followed by number of carbons:number of double bonds of the fatty acid esterified to the hydroxyl group at position 3.
  • In the case of unproven structures and other sterol esters (SE) the shorthand notation is used as above followed by slash number of carbons:number of double bonds of the fatty acid esterified to the hydroxyl group.
  • In the case of bile acids the shorthand notation is prefaced by A to indicate an acid and at the structure level the location of the acid group (CO2H) is indicated.
  • Precursor-ion scans reveal the presence of conjugating groups, i.e. taurine (T) or glycine (G), conjugated to the carboxylic acid group of bile acids through an amide bond, sulfuric acid (S) conjugated to a hydroxyl group through an ester bond, glucuronic acid (GlcA), N-acetylglucosamine (GlcNAc), and hexose (Hex) sugars assumed to be linked to a hydroxyl group through an acetal linkage.

Lipid class abbreviations

  • Sterols - ST
  • Steryl esters -SE
  • Free cholesterol - FC
  • Cholesteryl ester - CE
  • Bile acids:
    • Cholic acid - CA
    • Chenodeoxycholic acid - CDCA
    • Deoxycholic acid - DCA
    • Ursodeoxycholic acid - UDCA
    • Hyodeoxycholic acid - HDCA
    • Lithocholic acid - LCA
    • Glycocholic acid - GCA
    • Taurocholic acid - TCA

Examples

Bond type
Lipid class level mass$
Lipid species level§
Bond type level
LIPID MAPS Structure level
Cholesterol
ST (386)
ST 27:1_OH
ST 27:1_OH
ST 27:1/OH [5Z,3βOH ]
3β-Hydroxycholestenoic acid
ST (416)
ST A27:1_OH
ST A27:1_OH
ST A27:1/OH [5Z,3βOH,25(R),26CO2H]
Lithocholic acid
ST (376)
ST A24_OH
ST A24_OH
ST A24/OH [5βH,3αOH,24CO2H]
Progesterone
ST (314)
ST 21:3_OH2
ST 21:1_O2
ST 21:1/O2 [4Z,3O,20O]
Testosterone
ST (288)
ST 19:2_OH2
ST 19:1 _OH_O
ST 19:1/OH/O [4Z,17βOH,3O]
Dehydroepiandrosterone
ST (288)
ST 19:2_OH2
ST 19:1_OH_O
ST 19:1/OH/O [5Z,3βOH,17O]
17β-Estradiol
ST (272)
ST 18:3_OH2
ST 18:3_OH2
ST 18:3/OH2 [1Z,3E,5E,3OH,17βOH]
Taurocholic acid
ST (515)
ST A24_OH3_T
ST A24_OH3_T
ST A24/OH3/T [5βH, 3αOH,7αOH,12αOH,24T]
Glycochenodeoxycholic acid
ST (449)
ST A24_OH2_G
ST A24_OH2_G
ST A24/OH2/G [5βH, 3αOH,7αOH,24G]
Dehydroepiandrosterone sulfate
ST (368)
ST 19:2_OH2_S
ST 19:1_OH_O_S
ST 19:1/OH/O/S [5Z,3βOH,17O,3S]
24(S)-Hydroxycholesterol 3-sulfate, 24-glucuronide
ST (658)
ST 27:1_OH2_S_GlcA
ST 27:1_OH2_S_GlcA
ST 27:1/OH2/S/GlcA [5Z,3βOH,24(S)OH,3S,24GlcA]
Cholesteryl palmitate
ST (624)
SE 27:1/16:0
SE 27:1/16:0
CE 16:0
Cholesteryl linoleate
ST (648)
SE 27:1/18:2
SE 27:1/18:2
CE 18:2(9Z,12Z)
Zymosteryl oleate
ST (648)
SE 27:2/18:1
SE 27:2/18:1
SE 27:2 [5α,8E,24,3βFA]/18:1(9Z)

$ m is the uncharged molecular mass

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