Ursodeoxycholate

(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Formula: C24H40O4 (392.2926)
Chinese Name: 熊去氧胆酸, 熊脱氧胆酸
BioDeep ID: BioDeep_00000000066 ( View LC/MS Profile)
SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](C[C@H]1C[C@@H]3O)O



Found 25 Sample Hits

m/z Adducts Species Organ Scanning Sample
375.2858 [M+H-H2O]+
PPM:9.5
Marker Pen NA DESI (None)
3ul_0.8Mpa_RAW_20241016-PAPER PNMK - MEMI_test
Resolution: 30μm, 315x42

Description

By writing the four English letters “PNMK” on white paper with a marker pen, and then scanning with a DESI ion source to obtain the scanning result. The signal of the chemical substances on the marker pen used appears on the channel with an m/z value of 322.1918, 323.1953, 546.4010, and etc, from the single cell deconvolution sampling layer class_4. This test data was tested by chuxiaoping from PANOMIX’s R&D laboratory.

392.288 [M]+
PPM:10.4
Marker Pen NA DESI (None)
3ul_0.8Mpa_RAW_20241016-PAPER PNMK - MEMI_test
Resolution: 30μm, 315x42

Description

By writing the four English letters “PNMK” on white paper with a marker pen, and then scanning with a DESI ion source to obtain the scanning result. The signal of the chemical substances on the marker pen used appears on the channel with an m/z value of 322.1918, 323.1953, 546.4010, and etc, from the single cell deconvolution sampling layer class_4. This test data was tested by chuxiaoping from PANOMIX’s R&D laboratory.

393.2989 [M+H]+
PPM:2.6
Homo sapiens Liver MALDI (DHB)
20171107_FIT4_DHBpos_p70_s50 - Rappez et al (2021) SpaceM reveals metabolic states of single cells
Resolution: 50μm, 70x70

Description

393.2992 [M+H]+
PPM:1.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_17 - MTBLS58
Resolution: 17μm, 208x108

Description

1 male adult wild-type rat was obtained from Inserm U1085 - Irset Research Institute (University of Rennes1, France). Animals were age 60 days and were reared under ad-lib conditions. Care and handling of all animals complied with EU directive 2010/63/EU on the protection of animals used for scientific purposes. The whole epididymis was excised from each animal immediately post-mortem, loosely wrapped rapidly in an aluminum foil and a 2.5% (w/v) carboxymethylcellulose (CMC) solution was poured to embed the epididymis to preserve their morphology. To remove air bubbles, the filled aluminum molds was gently freezed by depositing it on isopentane or dry ice, then on the nitrogen vapors and finally by progressively dipping the CMC/sample coated with aluminum foil into liquid nitrogen (or only flush with liquid nitrogen). Frozen tissues were stored at -80 °C until use to avoid degradation.

393.2988 [M+H]+
PPM:2.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

393.2987 [M+H]+
PPM:3.1
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

392.3138 [M-H2O+NH4]+
PPM:5.4
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

393.2985 [M+H]+
PPM:3.6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

392.3136 [M-H2O+NH4]+
PPM:5.9
Rattus norvegicus normal MALDI (DHB)
epik_dhb_head_ito01_05 - MTBLS58
Resolution: 17μm, 183x105

Description

393.2982 [M+H]+
PPM:4.4
Rattus norvegicus normal MALDI (DHB)
epik_dhb_head_ito01_05 - MTBLS58
Resolution: 17μm, 183x105

Description

392.3138 [M-H2O+NH4]+
PPM:5.4
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_06 - MTBLS58
Resolution: 17μm, 183x103

Description

393.2984 [M+H]+
PPM:3.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_14 - MTBLS58
Resolution: 17μm, 205x103

Description

393.2969 [M+H]+
PPM:7.7
Mus musculus Lung MALDI (DHB)
image1 - MTBLS2075
Resolution: 40μm, 187x165

Description

Fig. 2 MALDI-MSI data from the same mouse lung tissue analyzed in Fig. 1. A: Optical image of the post-MSI, H&E-stained tissue section. B–D, F–G: Ion images of (B) m/z 796.6855 ([U13C-DPPC+Na]+), (C) m/z 756.5514 ([PC32:0+Na]+), (D) m/z 765.6079 ([D9-PC32:0+Na]+), (F) m/z 754.5359 ([PC32:1+Na]+), and (G) m/z 763.5923 ([D9-PC32:1+Na]+). E, H: Ratio images of (E) [D9-PC32:0+Na]+:[PC32:0+Na]+ and (H) [D9-PC32:1+Na]+:[PC32:1+Na]+. Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. U13C-DPPC, universally 13C-labeled dipalmitoyl PC; PC, phosphatidylcholine; MSI, mass spectrometry imaging; H&E, hematoxylin and eosin. Fig 1-3, Fig S1-S3, S5

393.2966 [M+H]+
PPM:8.4
Mus musculus Lung MALDI (DHB)
image3 - MTBLS2075
Resolution: 40μm, 146x190

Description

Fig. 4 MALDI-MSI data of mouse lung tissue after administration with D9-choline and U13C-DPPC–containing Poractant alfa surfactant (labels administered 12 h prior to tissue collection). Ion images of (A) m/z 796.6856 ([U13C-DPPC+Na]+), (B) m/z 756.5154 [PC32:0+Na]+), and (C) m/z 765.6079 ([D9-PC32:0+Na]+). D: Overlay image of [U13C-PC32:0+Na]+ (red) and [D9-PC32:0+Na]+ (green). Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

393.2967 [M+H]+
PPM:8.2
Mus musculus Lung MALDI (DHB)
image4 - MTBLS2075
Resolution: 40μm, 162x156

Description

Fig 6c Fig. 6 MALDI-MSI of U13C-PC16:0/16:0 acyl chain remodeling. A: Averaged MALDI mass spectrum from lung tissue collected from mice euthanized 12 h after administration of D9-choline and U13C-DPPC–containing Poractant alfa surfactant. The ion at m/z 828.6321 is assigned as the [M+Na]+ ion of 13C24-PC16:0_20:4 formed by acyl remodeling of U13C-PC16:0/16:0. The “NL” value refers to the intensity of the base peak in the full range MS1 spectrum. B: MS/MS spectrum of precursor ions at m/z 828.5 ± 0.5 with fragment ions originating from [13C24-PC16:0_20:4+Na]+ annotated. Part-per-million (ppm) mass errors are provided in parentheses. C, D: MALDI-MSI data of [U13C-DPPC+Na]+ (blue), [PC36:4+Na]+ (green) and [13C24-PC16:0_20:4+Na]+ (red) in lung tissue collected from mice (C) 12 h and (D) 18 h after label administration. All images were visualized using total-ion-current normalization and hotspot removal (high quantile = 99%). MS/MS, tandem mass spectrometry; MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

393.2971 [M+H]+
PPM:7.2
Mus musculus Lung MALDI (DHB)
image5 - MTBLS2075
Resolution: 40μm, 163x183

Description

Supplementary Figure S8. MALDI-MSI data of mouse lung tissue administered with D9-choline and U 13C-DPPC–containing Poractant alfa surfactant (labels administered 18 h prior to sacrifice). Ion images of (a) m/z 796.6856 ([U13C-DPPC+Na]+), (b) m/z 756.5154 [PC32:0+Na]+ and (c) m/z 765.6079 ([D9-PC32:0+Na]+). (d) Overlay image of [U13C-DPPC+Na]+ (red) and [D9-PC32:0+Na]+ (green). Parts per million (ppm) mass errors are indicated in parentheses. All images were visualised using totalion-current normalisation and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0.

393.2973 [M+H]+
PPM:6.7
Mus musculus Lung MALDI (DHB)
image2 - MTBLS2075
Resolution: 40μm, 550x256

Description

Supplementary Figure S6. Ion distribution images for (a) [PC36:4+Na]+ (m/z 804.5514) and (b) [PC38:6+Na]+ (m/z 828.5515) obtained from mouse lung tissue collected 6 h after administration of D9- choline and U13C-DPPC–containing CHF5633. Parts-per-million (ppm) mass errors are indicated in parentheses. (c) Magnification of the boxed region in (a) with selected bronchiolar regions outlined in white boxes. (d) The corresponding H&E-stained tissue section with the same selected bronchiolar regions outlined in black boxes. These data demonstrate the co-localisation of the polyunsaturated lipids PC36:4 and PC38:6 with the bronchiolar regions of the lung. All MSI images were visualised using total ion current normalisation and hotspot removal (high quantile = 99%).

393.2961 [M+H]+
PPM:9.7
Macropus giganteus Brain MALDI (BPYN)
170321_kangaroobrain-dan3-pos_maxof50.0_med1 - 170321_kangaroobrain-dan3-pos_maxof50.0_med1
Resolution: 50μm, 81x50

Description

Sample information Organism: Macropus giganteus (kangaroo) Organism part: Brain Condition: Wildtype Sample growth conditions: Wild

410.3229 [M+NH4]+
PPM:8.7
Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

357.2774 [M+H-2H2O]+
PPM:3.9
Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

410.3226 [M+NH4]+
PPM:9.4
Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

410.3235 [M+NH4]+
PPM:7.2
Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

357.2754 [M+H-2H2O]+
PPM:9.5
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

410.3203 [M+NH4]+
PPM:15
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

393.2973 [M+H]+
PPM:6.7
Drosophila melanogaster brain MALDI (DHB)
Drosophila18 - 2019-10-16_14h26m34s
Resolution: 5μm, 686x685

Description

Sample information Organism: Drosophila melanogaster Organism part: Brain Condition: Healthy Sample preparation Sample stabilisation: Frozen Tissue modification: Frozen MALDI matrix: 2,5-dihydroxybenzoic acid (DHB) MALDI matrix application: TM sprayer Solvent: Aceton/water MS analysis Polarity: Positive Ionisation source: Prototype Analyzer: Orbitrap Pixel size: 5μm × 5μm Annotation settings m/z tolerance (ppm): 3 Analysis version: Original MSM Pixel count: 469910 Imzml file size: 696.23 MB Ibd file size: 814.11 MB


Ursodeoxycholic acid is a bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of an ursodeoxycholate. Ursodeoxycholic acid is an epimer of [chenodeoxycholic acid]. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. Ursodiol is a Bile Acid. Ursodeoxycholic acid or ursodiol is a naturally occurring bile acid that is used dissolve cholesterol gall stones and to treat cholestatic forms of liver diseases including primary biliary cirrhosis. Ursodiol has been linked to rare instances of transient and mild serum aminotransferase elevations during therapy and to rare instances of jaundice and worsening of liver disease in patients with preexisting cirrhosis. Ursodeoxycholic acid is a natural product found in Myocastor coypus with data available. Ursodiol is a synthetically-derived form of ursodiol, a bile acid produced by the liver and secreted and stored in the gallbladder. Also produced by the Chinese black bear liver, ursodiol has been used in the treatment of liver disease for centuries. This agent dissolves or prevents cholesterol gallstones by blocking hepatic cholesterol production and decreasing bile cholesterol. Ursodiol also reduces the absorption of cholesterol from the intestinal tract. An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. See also: Dimethicone; pancrelipase; ursodiol (component of). Ursodeoxycholic acid, also known as ursodeoxycholate or acid deoxyursocholic, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Ursodeoxycholic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [HMDB] Ursodeoxycholic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=128-13-2 (retrieved 2024-07-02) (CAS RN: 128-13-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).