Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(20R,24R,25S)-3?,7?,12?,27-Tetra-acet-oxy-24,26-ep-oxy-5?-cholestane.

ABSTRACT: In the title anhydro-scymnol tetra-acetate, C(35)H(54)O(9), the fused chair conformation of the cyclo-hexane A/B ring junction is cis with a 5?-H configuration. The compound has a trimethyl-ene oxide ring at position 24,26 and four acetate groups at the 3?,7?,12?,27 positions.

SUBMITTER: Ketuly KA

PROVIDER: S-EPMC2977710 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(20R,24R,25S)-3α,7α,12α,27-Tetra-acet-oxy-24,26-ep-oxy-5β-cholestane.

Ketuly Kamal Aziz KA A Hadi A Hamid AH Ng Seik Weng SW

Acta crystallographica. Section E, Structure reports online 20090410 Pt 5

In the title anhydro-scymnol tetra-acetate, C(35)H(54)O(9), the fused chair conformation of the cyclo-hexane A/B ring junction is cis with a 5β-H configuration. The compound has a trimethyl-ene oxide ring at position 24,26 and four acetate groups at the 3α,7α,12α,27 positions. ...[more]

PMID: 21583846

Similar Datasets

Studies on the Importance of the 7α-, and 12α- hydroxyl groups of N-Aryl-3α,7α,12α-trihydroxy-5β-cholan-24-amides on their Antigermination Activity Against a Hypervirulent Strain of Clostridioides (Clostridium) difficile.

Project description:Chenodeoxycholic acid (CDCA) is a natural germination inhibitor for C. difficile spores. In our previous study (J. Med. Chem., 2018, 61, 6759-6778), we identified N-phenyl-3α,7α,12α-trihydroxy-5β-cholan-24-amide as an inhibitor of C. difficile strain R20291 with an IC50 of 1.8 μM. Studies of bile salts on spore germination have shown that chenodeoxycholate, ursodeoxycholate and lithocholate are more potent inhibitors of germination compared to cholate. Given this, we created amide analogs of chenodeoxycholic, deoxycholic, lithocholic and ursodeoxycholic acids using amines identified from our previous studies. We found that chenodeoxy- and deoxycholate derivatives were active with potencies equivalent to those for cholanamides. This indicates that only 2 out of the 3 hydroxyl groups are needed for activity and that the alpha stereochemistry at position 7 is required for inhibition of spore germination.

| S-EPMC9236192 | biostudies-literature

3?-Acet-oxy-6-hy-droxy-imino-cholestane.

Project description:Two independent mol-ecules comprise the asymmetric unit of the title cholestane derivative, C(29)H(49)NO(3) {systematic name: (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethyl-hex-yl]-6-hy-droxy-imino-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta-[a]phenanthren-3-yl ace-tate}. The major differences between the mol-ecules relate to the relative orientations of the terminal acetyl [C-C-O-C torsion angles = -158.8?(3) and -81.7?(3)°] and alkyl groups [C-C-C-C = 168.9?(3) and 65.8?(4)°]. In the crystal, the independent mol-ecules associate via pairs of O-H?N hydrogen bonds, forming dimeric aggregates. Supra-molecular layers in the ab plane are mediated by C-H?O inter-actions.

| S-EPMC3100065 | biostudies-literature

3β-Acet-oxy-12α-chloro-d-friedooleanan-28,14β-olide.

Project description:The title compound, C(32)H(49)ClO(4), was obtained along with nitrile and lactam products in the POCl(3)-catalysed Beckmann rearrangement from 3β-acet-oxy-12-hydroxyiminoolean-28-olic acid methyl ester. The mechanism of the transformation leading to the title compound remains unclear and requires further investigation. Rings A, B and E are in chair conformations, ring C has a twisted-boat conformation, ring D a conformation halfway between boat and twisted-boat and rings D and E are cis-fused. In the crystal, mol-ecules are connected by weak inter-molecular C-H⋯O hydrogen bonds into layers extending parallel to the bc plane.

| S-EPMC3051923 | biostudies-literature

(20R)-24-Bromo-5β-cholane.

Project description:In the title compound (5S,8R,9R,10R,13S,14S,17R,20R)-24-bromo-5β-cholane, C(24)H(41)Br, the fused-chair conformation of the cyclo-hexane A/B ring junction is cis with a 5β-H configuration.

| S-EPMC2977798 | biostudies-literature

(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetra-acet-oxy-2,13-bis-(benz-yloxy)-21-methyl-19,21-secohetisan-19-al hemi-hydrate.

Project description:In the crystal structure of the title compound, C(43)H(46)NO(13)·0.5H(2)O, the mol-ecule assumes a U-shaped conformation, the terminal benzene rings being approximately parallel and partially overlapped with each other. The mol-ecule contains eight alicyclic and heterocyclic rings. The cyclo-hexane rings adopt chair conformations, the other three six-membered carbocyclic rings form a bicyclo-[2.2.2]octane system with a boat conformation for each six-membered ring, the six-membered heterocyclic ring has a chair conformation and both of the five-membered rings have envelope conformations. The solvent water mol-ecule links with the organic mol-ecule via classic O-H⋯O and weak C-H⋯O hydrogen bonding in the crystal structure.

| S-EPMC2969740 | biostudies-literature

6β-Acet-oxy-1α,7β,11β,15β-tetra-hydr-oxy-7α,20-ep-oxy-ent-kaur-16-ene.

Project description:The title compound, C(22)H(32)O(7), a natural ent-kaurane diterpenoid also referred to as Maoyecrystal F, was obtained from the medicinal plant Isodon nervosa. There are four rings with the expected cis and trans junctions. Cyclohexane ring A adopts a chair conformation, rings B and C adopt boat conformations, while the five-membered ring has an envelope conformation. The mol-ecules stack along the a axis in the crystal and are linked together by inter-molecular O-H⋯O hydrogen bonds.

| S-EPMC2979918 | biostudies-literature

Comprehensive Bile Acid Profiling of ABCB4-mutated Patients and the Prognostic Role of Taurine-conjugated 3α,6α,7α,12α-Tetrahydroxylated Bile Acid in Cholestasis.

Project description:Background and aimsWe asked if comprehensive bile acid profiling could provide insights into the physiopathology of ABCB4-mutated patients and evaluated the prognostic value of taurine-conjugated tetrahydroxylated bile acid (tauro-THBA) in cholestasis.MethodsSerum bile acid profiles were evaluated in 13 ABCB4-mutated patients with 65 healthy controls by ultra-high-performance liquid chromatography/multiple-reaction monitoring-mass spectrometry (UPLC/MRM-MS). The concentration of tauro-THBA was compared between ABCB4-mutated patients with different prognoses. The areas under the curve (AUCs) of tauro-THBA were compared between ABCB11-mutated patients with native liver survival and those who died or underwent liver transplantation before 3 years of age by receiver operating characteristic curve (ROC), with another patient cohort for further verification.ResultsThe overall hydrophobicity indices of bile acids in ABCB4-mutated patients (12.99±3.25 m) were significantly lower than those of healthy controls (14.02±1.74 m, p<0.000). That was due to markedly increased bile acid modifications including conjugation, sulfation, and ketonization. Differences in the tauro-THBA concentration in ABCB4-mutated patients with different prognoses were not significant. ROC analysis indicated that levels of tauro-THBA of <60 nM yielded an AUC of 0.900 with a sensitivity of 80% and specificity of 87.5% for ABCB11-mutated patients with different prognoses (p=0.0192). Of the 15 patients with good prognosis, 14 were classified correctly and four of the five patients with a poor prognosis were classified correctly (14:15 vs. 1:5, p=0.005) with tauro-THBA as a classifier.ConclusionsTauro-THBA concentration may be a biomarker for predicting the clinical outcome in low gamma-glutamyl transferase intrahepatic cholestasis patients.

| S-EPMC10851069 | biostudies-literature

(22E,24R)-3α,5-Cyclo-5α-ergosta-22-en-6-one.

Project description:In the title mol-ecule, C(28)H(44)O, the two six-membered rings have a chair conformation and the two five-membered rings haveenvelope conformations. The crystal packing exhibits no short inter-molecular contacts. The absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of the title compound.

| S-EPMC3051649 | biostudies-literature

(1α,2β,3α,7α,11α,13β)-1,3,11-Triacet-oxy-2,13-bis-(benz-yloxy)-7-hydr-oxy-21-methyl-N,19-secohetisan-19-al.

Project description:The title compound (delgradine), C(41)H(43)NO(12), is a hetisine-type C(20)-diterpenoid alkaloid, isolated from the roots of Aconitum carmichaeli Debx. In the crystal structure, the mol-ecule assumes an U-shaped conformation, the terminal benzene rings being approximately parallel and partially overlapped with each other. The mol-ecule contains eight alicyclic and heterocyclic rings. Cyclo-hexane rings A and B adopt similar chair conformations; the six-membered rings C, D and E form a bicyclo-[2.2.2]octane system with a boat conformation for each six-membered ring, the six-membered heterocyclic ring F has a screw-boat conformation and both of the five-membered rings G and H have envelope conformations. The crystal structure contains inter-molecular O-H⋯O hydrogen bonding.

| S-EPMC2962025 | biostudies-literature

Poly[(?-2-acet-oxy-benzoato)(2-acet-oxy-benzoato)-?-aqua-mercury(II)].

Project description:In the title compound, [Hg(C(9)H(7)O(4))(2)(H(2)O)](n), the Hg(II) ion is five-coordinated by three acetylsalicylate anions and water leading to the formation of a coordination polymer extending parallel to (001). O-H?O and C-H?O hydrogen bonds are effective in the stabilization of the crystal structure.

| S-EPMC3212253 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data