Distinctive chemical features of cholesterol and analogs
| Trivial name | IUPAC nomenclature | 3-OH orientation | A/B junction |
| Cholesterol | (3S, 10R, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | n/aa |
| Epicholesterol | (3R, 10R, 13R, 17R)-10, 13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | α | n/aa |
| Coprostanol | (3S, 5R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | cis |
| Epicoprostanol | (3R, 5R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | α | cis |
| Cholestanol | (3S, 5S, 8R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | trans |
| Epicholestanol | (3R, 5S, 8R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | α | trans |
| Ent-cholesterol | (3R,8R,9R,10S,13S,14R,17S)-10,13-dimethyl-17-((S)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | n/aa |
| Trivial name | IUPAC nomenclature | 3-OH orientation | A/B junction |
| Cholesterol | (3S, 10R, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | n/aa |
| Epicholesterol | (3R, 10R, 13R, 17R)-10, 13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | α | n/aa |
| Coprostanol | (3S, 5R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | cis |
| Epicoprostanol | (3R, 5R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | α | cis |
| Cholestanol | (3S, 5S, 8R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | trans |
| Epicholestanol | (3R, 5S, 8R, 9S, 10S, 13R, 14S, 17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | α | trans |
| Ent-cholesterol | (3R,8R,9R,10S,13S,14R,17S)-10,13-dimethyl-17-((S)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | β | n/aa |
Because of the presence of the double bond at C5–C6 (Fig.1), the A/B junction presents neither cis nor trans geometry.