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. Author manuscript; available in PMC: 2021 Dec 29.
Published before final editing as: J Am Soc Mass Spectrom. 2020 Jun 29:10.1021/jasms.0c00015. doi: 10.1021/jasms.0c00015

Table 1.

Negative Ionization Mode DTCCSN2 Measurements for [M − H]− Ion Forms of Unsulfated Bile Acids Reported in This Studya

Sub-class Name Molecular Formula R1 R2 R3 R4 m/z DTCCSN2 (Å2) [M−H]− % RSD
dehydrolithocholic acid C24H38O3 =O −H −H −H 373.27 205.5 0.121
3,6-diketocholic acid C24H36O4 =O =O −H −H 387.25 200.9 0.223
dehydrodeoxycholic acid C24H36O4 =O −H −H =O 387.25 190.7 0.818
3-oxo-12α-cholic acid C24H38O4 =O −H −H α−OH 389.27 200.8 0.027
3,7,12-tri-betacholanic acid C24H34O5 =O −H =O =O 401.23 192.4 0.049
7,12-dioxolithocholic acid C24H36O5 −OH −H =O =O 403.25 190.3 0.188
7-ketodeoxvcholic acid C24H38O5 α−OH −H =O α−OH 405.26 204.2 0.044
aoocholic acid C24H38O4 α−OH −H −H α−OH 389.27 189.1 0.246
7α, 12α, dihydroxy-5β-cholanic acid C24H40O4 −H −H α−OH α−OH 391.28 200.6 0.079
3β, 7α, dihydroxy-5β-cholanic acid C24H39DO4 β−OH, α−D −H α−OH −H 392.29 202.7 0.043
lithocholic acid C24H40O3 α−OH −H −H −H 375.29 198.9 0.307
chenodeoxycholic acid C24H40O4 α−OH −H α−OH −H 391.28 202.3 0.079
hyodeoxycholic acid C24H40O4 α−OH α−OH −H −H 391.28 199.2 0.241
murideoxycholic acid C24H40O4 α−OH β−OH −H −H 391.28 200.3 0.241
ursodeoxycholic acid C24H40O4 α−OH −H β−OH −H 391.28 198.3 0.198
cholic acid C24H40O5 α−OH −H α−OH α−OH 407.28 202.9 0.146
hyocholic acid C24H40O5 α−OH α−OH α−OH −H 407.28 190.1 0.166
α-muricholic acid C24H40O5 α−OH β−OH α−OH −H 407.28 192.4 0.120
β-muricholic acid C24H40O5 α−OH β−OH β−OH −H 407.28 190.8 0.075
glycolithocholic acid C26H43NO4 α−OH −H −H −H 432.31 199.5 0.097
glycodeoxycholic acid C26H43NO5 α−OH −H −H α−OH 448.31 199.9 0.079
glycoursodeoxycholic acid C26H43NO5 α−OH −H β−OH −H 448.31 201.1 0.062
glycocholic acid C26H43NO6 α−OH −H α−OH α−OH 464.30 202.2 0.041
taurolithocholic acid C26H45NO5S α−OH −H −H −H 482.29 206.4 0.062
taurochenodeoxycholic acid C26H45NO6S α−OH −H α−OH −H 498.29 207.2 0.080
taurohyodeoxycholic acid C26H45NO6S α−OH α−OH −H −H 498.29 206.3 0.087
tauroursodeoxycholic acid C26H45NO6S α−OH −H β−OH −H 498.29 207.6 0.061
taurocholic acid C26H45NO7S α−OH −H α−OH α−OH 514.28 207.6 0.079
taurohyocholic acid C26H45NO7S α−OH α−OH α−OH −H 514.28 208.4 0.083
tauro-α-muricholic acid C26H45NO7S α−OH β−OH α−OH −H 514.28 209.4 0.067
tauro-β-muricholic acid C26H45NO7S α−OH β−OH β−OH −H 514.28 209.5 0.115
tauro-ω-muricholic acid C26H45NO7S α−OH α−OH β−OH −H 514.28 209.3 0.297
a

Bile acids are grouped by subclass, and entries within each subclass are sorted by increasing m/z ratio. Structural nomenclature and composition of the R groups are displayed in the table along with chemical formula and m/z. Numeration of the R groups refers to positions shown in Figure 1. At each R position, the substituent was either hydrogen (−H), alpha or beta hydroxyl (α- or β-OH), or doubly bonded oxygen (=O). Precision is reported as relative standard deviation (%RSD) for n = 3 measurements made on three separate days. The subclasses are color coded in the leftmost column, with grey representing oxidized bile acids, yellow representing unsaturated bile acids, purple representing atypical bile acids, blue representing unconjugated bile acids, orange representing glycine conjugated bile acids, and green representing taurine conjugated bile acids. Values for ion forms observed in positive ionization mode are reported in the accompanying Supplemental Information (Table S1). Additional measurements taken in negative ionization mode are reported in Tables S2 and S3.