Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

6β,8β-Dihy-droxy-eremophil-7(11)-en-8α,12-olide.

ABSTRACT: The title compound, C(15)H(22)O(4), an eremophilane sesquiternoid, was isolated from the roots of Ligularia virgaurea. Both six-membered rings (A and B) adopt chair conformations and the five-membered ring is almost planar (r.m.s. deviation = 0.016 Å). The two methyl and two hy-droxy groups adopt a syn conformation and the A/B ring junction is cis-fused. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into [100] chains.

SUBMITTER: Zhang ZX

PROVIDER: S-EPMC3247365 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

6β,8β-Dihy-droxy-eremophil-7(11)-en-8α,12-olide.

Zhang Zhan-Xin ZX Fei Dong-Qing DQ

Acta crystallographica. Section E, Structure reports online 20111012 Pt 11

The title compound, C(15)H(22)O(4), an eremophilane sesquiternoid, was isolated from the roots of Ligularia virgaurea. Both six-membered rings (A and B) adopt chair conformations and the five-membered ring is almost planar (r.m.s. deviation = 0.016 Å). The two methyl and two hy-droxy groups adopt a syn conformation and the A/B ring junction is cis-fused. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into [100] chains. ...[more]

PMID: 22219983

Similar Datasets

6β-Hy-droxy-eremophil-7(11)-en-8β,12-olide.

Project description:The title eremophilenolide, C(15)H(22)O(3), is a natural compound isolated from Senecio laetus Edgew. The two cis-fused six-membered rings have chair confomations and the five-membered ring has a planar envelope conformation [maximum deviation = 0.010 (1) Å]. The β-hy-droxy group participates in inter-molecular O-H⋯O hydrogen bonding, forming mol-ecular chains along the a axis.

| S-EPMC3120521 | biostudies-literature

3β-Acet-oxy-8β,10β-dihy-droxy-6β-meth-oxy-eremophil-7(11)-en-8,12-olide.

Project description:The title compound, C(18)H(26)O(7), is an eremophilenolide which has been isolated from the plant Ligularia duciformis for the first time. The present study confirms the atomic connectivity assigned on the basis of (1)H and (13)C NMR spectroscopy. The mol-ecule contains three fused rings, two six-membered rings in chair confomations and a five-membered ring in a flattened envelope conformation. Two hy-droxy groups are involved in formation of intra- and inter-molecular O-H⋯O hydrogen bonds. The latter ones link mol-ecules into chains propagating in [010].

| S-EPMC3007320 | biostudies-literature

5α-Hy-droxy-eudesm-4(15),11(13)-dien-8β,12-olide.

Project description:The title compound, C(15)H(20)O(3), a sesquiterpene lactone, was isolated from the aerial parts of Carpesium minus Hemsl. (Compositae). The mol-ecule is composed of three rings, with the two cyclo-hexane rings in chair conformations and the cyclo-pentane ring adopting a twist conformation. The A/B ring junction is trans-fused. The absolute configuration shown has been arbitrarily assigned. In the crystal, mol-ecules are linked into [100] chains by O-H⋯O hydrogen bonds.

| S-EPMC3344144 | biostudies-literature

Crystal structure of 4α-hy-droxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate.

Project description:The title compound, C15H22O3·H2O, is a natural producr isolated from Chloranthus japonicus, which is a eudesmane sesquiterpenoid. The two trans-fused six-membered rings have chair confomations. In the crystal, O-H⋯O hydrogen bonds link the components into corrugated layers parallel to the bc plane. There are C-H⋯O inter-actions present within and between the layers.

| S-EPMC4518932 | biostudies-literature

3β,6β-Diacet-oxy-5,9α-dihy-droxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate.

Project description:The title compound, C31H48O7·0.04CH3COOH, is a polyoxy-genated steroid obtained by selective chemical oxidation of 7-de-hydro-cholesteryl acetate. The asymmetric unit comprises three mol-ecules of the steroid (Z' = 3) and a mol-ecule of acetic acid which has occupancy factor 0.131 (5). The geometric parameters of the independent mol-ecules do not reveal significant differences. In one mol-ecule, the terminal isopropyl group is disordered over two sets of sites with occupancy ratio 0.869 (5):0.131 (5). The three mol-ecules reveal different hydrogen-bonding patterns. Each of them is involved in an intra-molecular S(6) hydrogen-bonding motif, involving hy-droxy groups as donor and acceptor. In the crystal, two independent mol-ecules form dimers through hydrogen bonding between an OH donor and an acetate carbonyl acceptor, giving rise to R 2 (2)(16) ring patterns. A single hydrogen bond between the OH group and a ketone carbonyl group is observed between two symmetry-independent mol-ecules.

| S-EPMC3685037 | biostudies-literature

8β-Eth-oxy-eremophil-3,7(11)-diene-8α,12;6α,15-diolide.

Project description:The title compound, C17H20O5, an eremophilane sesquiternoid, was isolated from the roots of Ligularia lapathifolia. The mol-ecule contains four fused rings of which the six-membered ring A adopts a half-chair conformation, the six-membered ring B adopts a chair conformation, the five-membered ring C is almost planar (r.m.s. deviation = 0.015 Å) and the five-membered ring D adopts an envelope conformation with the quaternary C atom as the flap. The methyl and the eth-oxy groups adopt a syn conformation and the A/B ring junction is cis-fused. No directional inter-molecular inter-actions could be identified in the crystal.

| S-EPMC3770365 | biostudies-literature

4α,6α-Dihy-droxy-1β-methyl-sulfonyl-8α,9α-ep-oxy-2β,12-epoxymethano-β-dihydro-agarofuran.

Project description:The title mol-ecule, C(16)H(24)O(8)S, is a dihydro-agrofuran derivative and has a heteropolycyclic structure. One cyclohexane ring exhibits a chair conformation and the other a non-chair conformation. In the crystal structure there is an inter-molecular C-H⋯O hydrogen-bonding inter-action to stabilize the packing.

| S-EPMC3200600 | biostudies-literature

3β,6α-Diacet-oxy-5,9α-dihy-droxy-5α-cholest-7-en-11-one.

Project description:The title compound, C31H48O7, a polyoxygenated steroid, was obtained by chemical oxidation of 7-de-hydro-cholesteryl acetate. The mol-ecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intra-molecular S(6) O-H⋯O hydrogen-bonding motif involving a hy-droxy donor and acceptor is observed. In the crystal, chains of mol-ecules running along the b axis are formed via O-H⋯O hydrogen bonds between hy-droxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 21 screw axes.

| S-EPMC3770383 | biostudies-literature

(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy-droxy-3,7-dimethyl-11-methyl-idene-13-oxabicyclo-[8.3.0]tridec-6-en-12-one.

Project description:The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair-chair conformation. The dihedral angle between the two rings is 66.4 (2)°. In the crystal, mol-ecules are linked into chains propagating along the a axis by O-H⋯O hydrogen bonds.

| S-EPMC3247566 | biostudies-literature

Propargylaminyl 3α-hy-droxy-11-oxo-18β-olean-12-en-29-oate.

Project description:The title compound, C(33)H(49)NO(3), is the propargyl-amide of 18β-glycyrrhetinic acid, a penta-cyclic triterpenoid of inter-est as a therapeutic agent. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring C in a half-chair conformation. In the crystal, the terminal N-propargylcarboxamide group has remarkable structural effects on weak hydrogen-bond-like inter-actions. Particularly noteworthy are an inter-molecular O-H⋯π inter-action accepted side-on by the terminal alkyne group [O⋯C = 3.097 (2) and 3.356 (2) Å] and a short inter-molecular C-H⋯O inter-action [C⋯O = 3.115 (2) Å] donated by the alkyne C-H group. An N-H⋯O [N⋯O = 3.251 (2) Å] and a C(alkyl)-H⋯O [C⋯O = 3.254 (2) Å] interaction complement the crystal structure.

| S-EPMC3247445 | 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