Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)

RF-9. Derivatives of Parent Structures

Continued from RF-8. Bond Order Modifications

Contents of this section

RF-9. Derivatives of Parent Structures

Derivatives of parent structures are named according to the usual methods of systematic organic nomenclature (ref 2, 3) as far as possible.

RF-9.1. Prefixes and Suffixes

The prefixes and suffixes of organic nomenclature are used in the prescribed manner to name atoms and groups that are considered to substitute for hydrogen atoms of parent structures. In naming derived acids and related characteristic groups, unmodified parent structures are used as far as possible.


8α-Ethyleudesmane11-oxo-5α-cholan-24-oic acid

Aspidospermidine-21-carboxylic acid1(14)a-Homoeburnamenin-1a-one error details


RF-9.2. Modifications to Principal Characteristic Groups

Modifications to principal characteristic groups, such as esters, acetals, etc., are named by the usual methods of organic nomenclature. Cyclic modifications, such as lactones, cyclic acetals, etc., are named preferably as such rather than as fused ring, bridged, or spiro modified parent structures (see also RF-6.1).


Methyl 5β-androstane-17β-carboxylateAspidospermidin-4-one ethylene dithioketal error details

RF-9.3. Substituent Prefix Names

Substituent prefix names for natural product parent structures may be formed in the usual way by adding a suffix, such as "-yl", "-diyl", "-ylidene", to the name of the parent structure with elision of the final "e", if any, of the parent structure name before "y".


3α-Hydroxy-5α-androstan-17β-yl butyrate

Acetaldehyde 4,5α-epoxy morphinan-6β,7β-diyl acetal(1R)-1-(17-Norcorynan-16-yl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
error details

RF-9.4. Ring Assemblies and Spiro Derivatives

Ring assemblies and spiro derivatives of parent structures are named in the usual manner (ref 2, 3).


(4ξ)-2,2,6'-Trimethyl-9',10'-didehydrospiro[1,3-dioxolane-4,8'-ergoline] error details11,11',12,12'-Tetradehydro-

Note: In the ring assembly name (dione) above the hydroxy group is created by the seco operation. To provide for the explicit citation of the hydroxy group as a substituent, the oxygen atom could be removed first using the nor operation; this would be followed by the seco operation and the addition of the prefix "hydroxy-".

References for this section

2. International Union of Pure and Applied Chemistry, Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, l979 edition, Pergamon Press, Oxford, 1979.

3. International Union of Pure and Applied Chemistry, A Guide to IUPAC Nomenclature of Organic Compounds, Blackwell Scientific Publications, Oxford, 1993. [Corrections see Pure Appl. Chem., 71, 1327-1330 (1999).]

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