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Stereoisomerism

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Definition: The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)  NIM; policy: Manual 25.5.5.1    Other names Stereoisomers; Molecular Stereochemistry; Stereoisomer; Stereochemistry, Molecular
 
SubstanceCAS Registry & nameCategoriesSource
(6R,7S,11R,10S)-15-hydroxy-sesquisabinene hydrate  0   *Sesquiterpenes Stereoisomerism. J Asian Nat Prod Res. 2012;14(3):224-34
2beta,3beta,19alpha,24-tetrahydroxyurs-12-en-28-oic acid  0   *Pentacyclic Triterpenes Stereoisomerism. J Asian Nat Prod Res. 2012 Feb;14(2); 97-104
(S)-(+)-4'-O-senecioyl-5-O-methylvisamminol  0   *Chromones Stereoisomerism. J Nat Prod. 2008 Nov;71(11):1956-60
(S)-(+)-4'-O-angeloyl-5-O-methylvisamminol  0   *Chromones Stereoisomerism. J Nat Prod. 2008 Nov;71(11):1956-60
7,8-seco-7,8-oxacassa-13,15-diene-7,17-diol  0   *Diterpenes Stereoisomerism. J Nat Prod. 2011 Sep 23;74(9):1946-51
(2S,3S)-sulfated pterosin C  0   *Indans *Sesquiterpenes *Sulfuric Acid Esters Antineoplastic Agents, Phytogenic Stereoisomerism. J Nat Prod. 2011 Sep 23;74(9):2010-3
pyridinopyrone B  0   *Polyenes *Pyridines Stereoisomerism. J Nat Prod. 2011 Aug 26;74(8):1773-8
3,7,12-trihydroxycholestan-27-oic acid  0   *Cholestanols Stereoisomerism. Chem Phys Lipids. 2011 Jul;164(5):368-77
alpha-(E)-acaridiol 8-O-beta-D-glucopyranoside  0   *Glycosides *Monoterpenes Stereoisomerism. J Asian Nat Prod Res. 2011 Sep;13(9):845-50
trans-dimer D, Axinyssa variabilis  0   *Sesquiterpenes Stereoisomerism. J Asian Nat Prod Res. 2011 Aug;13(8):770-5
(6E,12Z)-tetradecadiene-8,10-diyne-1,3-diol  0   *Fatty Alcohols *Diynes Stereoisomerism. J Asian Nat Prod Res. 2011 Apr;13(4):346-9
phenanthrene tetraol  0   *Phenanthrenes Stereoisomerism. Chem Res Toxicol. 2011 Feb 18;24(2):262-8
macrophylline A  0   *Indole Alkaloids Stereoisomerism. J Nat Prod. 2011 Jan 28;74(1):12-5
schizanthine N  0   *Tropanes Alkaloids Stereoisomerism. J Nat Prod. 2011 Jan 28;74(1):50-3
beta-isocryptoxanthin  0   *Xanthophylls Stereoisomerism. Nat Prod Commun. 2010 Nov;5(11):1733-6
(2R)-7-methoxyl-8-hydroxyethyl-4'-hydroxylflavane-2'-O-beta-D-glucopyranoside  0   *Flavonoids *Glucosides Stereoisomerism. J Asian Nat Prod Res. 2010 Aug;12(8):680-4
(1S,4S,5S)-5-exo-hydroxycamphor 5-O-beta-D-glucopyranoside  0   *Glycosides *Monoterpenes Stereoisomerism. Planta Med. 2010 Mar;76(5):461-4
neopuerarin A  0   *Glucosides *Isoflavones Stereoisomerism. J Asian Nat Prod Res. 2010 Apr;12(4):293-9
(5S(*),6R(*),7S(*))-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one  0   *Chromones Stereoisomerism. J Asian Nat Prod Res. 2010 Feb;12(2):134-7
malyngamide C  0   *Cyclohexanones *Fatty Acids, Monounsaturated Stereoisomerism. J Nat Prod. 2010 Mar 26;73(3):463-6
mattucinol-7-O-(4'',6''-O-(aS)-hexahydroxydiphenoyl)-beta-D-glucopyranoside  0   *Glycosides *Flavanones Stereoisomerism. J Nat Prod. 2009 Mar 27;72(3):327-35
tribufuroside D  0   *Saponins *Steroids Stereoisomerism. J Asian Nat Prod Res. 2009 Jun;11(6):548-53
brucojavan 2  0   *Sesquiterpenes Stereoisomerism. J Asian Nat Prod Res. 2009 Jun;11(6):539-47
2,10-diacetyl-5(Z)-cinnamoylphototaxicin II  0   *Taxoids Stereoisomerism. J Asian Nat Prod Res. 2009 Jun;11(6):534-8
conicol  0   *Terpenes Stereoisomerism. Org Lett. 2010 Feb 19;12(4):776-9
lamiridosin A  0   *Iridoids Stereoisomerism. J Nat Prod. 2009 Dec;72(12):2158-62
gabosine O  0   *Cyclohexanones Stereoisomerism. Org Lett. 2009 Nov 5;11(21):5070-3
3alpha-hydroxy chlormadinone acetate  0   Chlormadinone Acetate Stereoisomerism. Pharmacology. 2009;84(2):74-81
saccharomicin A  0   *Oligosaccharides Stereoisomerism. Org Lett. 2009 Nov 5;11(21):4850-3
xanalteric acid I  0   *Benzopyrans Stereoisomerism. J Nat Prod. 2009 Nov;72(11):2053-7
terricollene A  0   *Phenyl Ethers Stereoisomerism. J Nat Prod. 2009 Oct;72(10):1782-5
(25S)-26-O-beta-D-glucopyranosyl-furost-1beta,3beta,5beta,22alpha, 26-pentaol-3-O-beta-D-glucoside  0   *Saponins *Sterols Stereoisomerism. Magn Reson Chem. 2009 Jul;47(7):613-6
isomyrmicarin 430B  0   *Heterocyclic Compounds, 3-Ring Alkaloids Stereoisomerism. Org Lett. 2009 Jul 16;11(14):2960-3
breviflavone A  0   *Flavonoids Stereoisomerism. J Pharm Biomed Anal. 2009 Apr 5;49(3):853-7
scuteflorin A  0   *Pyranocoumarins Stereoisomerism. J Nat Prod 2009 Jun;72(6):983-7
(25R)-22-O-methyl-furost-5-en-3beta,26-diol-3-O-alpha-L-rhamnopyranosyl-(1-2)-beta-D-glucopyranoside  0   *Saponins *Sterols Stereoisomerism. Bioorg Med Chem Lett 2009 May 15;19(10):2796-800
isonuatigenone  0   *Spiro Compounds *Triterpenes Stereoisomerism. Appl Environ Microbiol 2009 Jun;75(12):4202-5
arenophthalide B  0   *Benzofurans *Glycosides Stereoisomerism. J Asian Nat Prod Res 2009;11(4):352-6
dihydrolyfoline  0   *Alkaloids *Quinolizidines Stereoisomerism. J Nat Prod 2009 Apr;72(4):749-52
(6Z,8E)-undeca-6,8,10-trien-4-one  0   *Polyenes Stereoisomerism. J Agric Food Chem 2009 Feb 25;57(4):1433-9
cyclic-tris-(R)-valineselenazole  0   *Peptides, Cyclic Stereoisomerism P-Glycoprotein/antagonists & inhibitors. Science 2009 Mar 27;323(5922):1718-22
neovibsanin A  0   *Diterpenes Stereoisomerism. Org Lett 2009 Mar 19;11(6):1253-5
28-norlup-20(29)-en-3beta-hydroxy-17beta-hydroperoxide  0   *Triterpenes Stereoisomerism. J Nat Prod 2008 Oct;71(10):1787-90
suspensoside A  0   *Glycosides *Pheromones Stereoisomerism. J Nat Prod 2008 Oct;71(10):1726-31
11alpha H-6 beta-angeloyloxy-15-carboxyeremophil-7-en-12,8-olide  0   *Sesquiterpenes Stereoisomerism. Phytochemistry 2008 Mar;69(5):1158-65
3beta-OH-tibolone  0   *Norpregnanes Stereoisomerism. Menopause 2008 Mar-Apr;15(2):386-7
2-dodecenoic acid  0   *Fatty Acids, Monounsaturated Stereoisomerism. ISME J 2008 Jan;2(1):27-36
3alpha, 24-dihydroxyurs-12-ene  0   *Triterpenes Stereoisomerism. Apoptosis 2007 Oct;12(10):1911-26
11-alpha-methoxycurvularin  0   Zearalenone/*analogs & derivatives Stereoisomerism. J Org Chem 2007 Dec 7;72(25):9846-9
sanionin A  0   *Bibenzyls Stereoisomerism. Prep Biochem Biotechnol 2007;37(4):343-52
2,3-isopropylidenedioxy-6,6-ethylenedioxy-5alpha-androst-15-en-17-one  0   *Androstenes Stereoisomerism. Bioorg Khim. 2007 May-Jun;33(3):342-8
isosilybin A  0   Silymarin/*analogs & derivatives Stereoisomerism. Carcinogenesis 2007 Jul;28(7):1533-42
3beta,8alpha-dihydroxy-13-methoxyl-4(14),10(15)-dien-(1alphaH,5alphaH,6beta H,11betaH)-12,6-olide  0   *Sesquiterpenes, Guaiane Stereoisomerism. Nat Prod Res 2007 Mar;21(3):221-6
14-deoxy-9-oxygigantecin  0   *Furans *Lactams Stereoisomerism. Org Lett 2006 Jul 20;8(15):3383-6
4-oxo-4-(2-pyridinylamino)butanoic acid  0   *Pyridines Stereoisomerism. J Colloid Interface Sci 2007 Mar 1;307(1):280-7
cinnamtannin B-1  0   *Proanthocyanidins Stereoisomerism. Arch Biochem Biophys 2007 Jan 15;457(2):235-42; J Nat Prod. 2011 Sep 23;74(9):1833-41
triumphalone  0   *Ketones Stereoisomerism. Phytochemistry 2006 Sep;67(18):2085-9
gabosine N  0   *Cyclohexanones Stereoisomerism. Org Lett 2006 Apr 13;8(8):1617-20
2-hydroxymethyl-3-methylcyclopent-2-enone  0   *Cyclopentanes Stereoisomerism. J Nat Prod 2006 Sep;69(9):1351-3
methyl 27-O-caffeoylcylicodiscate  0   *Triterpenes Stereoisomerism. J Nat Prod 2006 Aug;69(8):1218-21
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012

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