Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid.

ABSTRACT: The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H?O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along [010]. The absolute configuration of the compound was assigned on the basis of optical rotation measurements.

SUBMITTER: Beattie KD

PROVIDER: S-EPMC3275267 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid.

Beattie Karren D KD Bhadbhade Mohan M MM Craig Donald C DC Leach David N DN

Acta crystallographica. Section E, Structure reports online 20120125 Pt 2

The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H⋯O hydrogen bond in the crystal lattice, forming hydr ...[more]

PMID: 22347123

Similar Datasets

3α-Hy-droxy-tirucalla-8,24-dien-21-oic acid.

Project description:The title compound, C(30)H(48)O(3), a triterpene isolated from the resin of canarium schweinfurthiiand, is an isomer of the previously reported triterpene 3α-hy-droxy-tirucalla-7,24-dien-21-oic acid [Mora et al. (2001 ▶). Acta Cryst. C57, 638-640], which crystallizes in the same trigonal space group. The title mol-ecule consists of four fused rings having chair, half-chair, half-chair and envelope conformations for rings A, B, C and D, respectively (steroid labelling). An intra-molecular C-H⋯O hydrogen bond generates an S(7) ring. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O inter-actions, forming (001) sheets.

| S-EPMC3099970 | biostudies-literature

A cocrystal of 3α-hy-droxy-tirucalla-8,24-dien-21-oic acid and 3β-fluoro-tirucalla-7,24-dien-21-oic acid (0.897:0.103).

Project description:The title compound, 0.897C(30)H(48)O(3).0.103C(30)H(47)O(2)F is a co-crystal of two triterpenes isolated from the resin of Canarium schweinfurthiiand Engl. Both triterpenes consists of four trans-fused rings having chair/half-chair/half-chair and envelope conformations. The mol-ecular conformations are stabilized by intra-molecular C-H⋯O hydrogen bonds, forming rings of S(7) graph-set motif. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O and C-H⋯O inter-actions, forming sheets parallel to (001). All atoms. excepting the axially-oriented hydroxyl group in the major component and the equatorially-oriented fluorine atom in the minor component, are overlapping.

| S-EPMC3099936 | biostudies-literature

11,20-Dihy-droxy-3-oxopregna-1,4-dien-21-oic acid monohydrate.

Project description:The title compound, C(21)H(28)O(5)·H(2)O, is the hydrate of a steroid derivative and was obtained by degradation of solid prednisolone sodium phosphate. The six C atoms in ring A are nearly co-planar with a mean deviation of 0.015?Å. Rings B and C are both in chair conformations, while ring D has an envelope form. In the crystal, inter-molecular O-H?O hydrogen-bonding inter-actions occur between the hy-droxy groups, carbonyl O atoms and solvent water mol-ecules, resulting in an overall three-dimensional structure.

| S-EPMC3120479 | biostudies-literature

(4S,5S,6S)-4-Hy-droxy-3-meth-oxy-5-methyl-5,6-ep-oxy-cyclo-hex-2-en-1-one.

Project description:The title compound, C(8)H(10)O(4), was isolated from culture extracts of the endophytic fungus Xylaria sp. (PB-30). The cyclo-hexenone ring exhibits a flattened boat conformation. In the crystal structure, mol-ecules related by translation along the b axis are linked into chains through O-H⋯O hydrogen bonds. Weak non-classical C-H⋯O contacts are also observed in the structure.

| S-EPMC3008014 | biostudies-literature

(1S,2S,3R,4S,5R,7S,8S,10R,13S)-2-Debenzoyl-10-deacetyl-2-(3-fluoro-benzo-yl)-7,10-bis-(2,2,2-trichloro-eth-oxy-carbon-yl)baccatin III ethyl acetate monosolvate monohydrate.

Project description:In the title compound, C(35)H(37)Cl(6)FO(14)·C(4)H(8)O(2)·H(2)O, the absolute configurations (1S,2S,3R,4S,5R,7S,8S,10R,13S) for the nine chiral centres of the mol-ecule has been determined. In the crystal, mol-ecules are linked by O-H⋯O and O-H⋯Cl hydrogen bonds.

| S-EPMC3051954 | biostudies-literature

17?-Hy-droxy-17?-methyl-androsta-1,4-dien-3-one.

Project description:The title compound, C20H28O2, is a steroid with strong anabolic properties. The present solvent-free form crystallizes with two mol-ecules per asymmetric unit. In the crystal, both mol-ecules are involved in the formation of O-H?O hydrogen-bonded chains which extend along the b-axis direction.

| S-EPMC3588272 | biostudies-literature

(1R,2S,4S,4aS,8S,8aS)-4-Hy-droxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexa-hydro-1H-4a,1-(ep-oxy-methano)-naphthalen-2-yl acetate.

Project description:The title compound, C15H20O5, presents a bis-norsesquiterpene skeleton, with a trans-deca-line backbone constrained by the lactone bridge. The α-hy-droxy substituent and the methyl group belonging to the two deca-line rings are in axial positions, whereas the other methyl group and the acyl group occupy the sterically preferred equatorial positions. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules are linked into chains along [010] by O-H⋯O hydrogen bonds.

| S-EPMC3685084 | biostudies-literature

(3R,4S,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]tetra-hydro-furan-2-one.

Project description:The title compound, C(11)H(18)O(3), was synthesized to prove the relative configuration of the corresponding acyclic C1-C8 stereopentade. It crystallizes with two mol-ecules in the asymmetric unit, which show only slight differences. The mol-ecules are linked via O-H⋯O hydrogen bonds, resulting in two crystallographically independent chains of mol-ecules propagating in the a-axis direction. The absolute configuration was known from the synthesis.

| S-EPMC2962143 | biostudies-literature

(1R,2R,3R,4S,5S)-3-Methyl-8-oxa-bicyclo-[3.2.1]oct-6-ene-2,4-diyl diacetate.

Project description:The mol-ecule of the title compound, C(12)H(16)O(5), has crystallographically imposed mirror symmetry with the mirror plane passing through the endocyclic O atom and the mid-point of the double bond. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming chains running along the a axis.

| S-EPMC3213568 | biostudies-literature

Potassium (1R,4R,5S,8S)-4,5,8-trihy-droxy-3-oxo-2,6-dioxabicyclo-[3.3.0]octane-4-sulfonate dihydrate.

Project description:The title salt, K(+)·C6H7O9S(-)·2H2O, formed by reaction of dehydro-l-ascorbic acid with potassium hydrogen sulfite in water, crystallizes as colourless plates. The potassium ion is coordinated by eight O atoms arising from hy-droxy or sulfonate groups. The sulfonate group is bonded to the C atom neighbouring that of the lactone carbonyl group. As is commonly observed in crystalline l-ascorbic acid derivatives, the O atom of the primary hy-droxy group is linked to the second C atom from the lactone C atom, forming a hemi-acetal function, thereby creating a bicyclic system of two fused five-membered rings, both of which have envelope conformations with one of the shared C atoms as the flap. Addition of the sulfur nucleophile occurs from the less hindered face. One of the two independent lattice water mol-ecules has hydrogen bonds to sulfonate O atoms of two different anions and is the acceptor of bonds from hy-droxy groups of two further anions; the second lattice water mol-ecule donates to the carbonyl and a hy-droxy O atom in different anions, and accepts from a hy-droxy O atom in a further anion. Thus, through K-O coordination and hydrogen bonds, the potassium cations, sulfonate anions and water mol-ecules are linked in a three-dimensional network.

| S-EPMC3588254 | 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