Continued from Recommendations and Table 1

Contents (continued)

Table 2. Representative oligophosphoric esters (oligophosphates)
Table 3. Representative bisnucleoside phosphates and cyclic phosphates
Table 4. Representative phospholipids (involving diesterified phosphoric acid)
Table 5. Phosphoric amides (phosphoramidic acids or amidophosphoric acids)
Table 6. Representative phosphoric anhydrides and fluorophosphates
Table 7. Representative C-phosphonates
Table 8. Adenosine 5'-triphosphate analogs

	Recommended names	Other names	Abbreviationsa	Structure
1.	Farnesyl diphosphate; farnesol diphosphate	Farnesyl trihydrogen   diphosphate; farnesol (trihydrogen   diphosphate)
2.	Adenosine 5'-diphosphateb	5'-Diphosphoadenosine; 5'-adenylyl phosphate	adenosine-5'PP; Ado5'PP; PPAdo; ADP
3.	5-Phospho-α-D-ribosyl   diphosphatec; α-D-ribosyl   diphosphate   5-phosphate	5-O-Phosphono-α-D-ribosyl diphosphate; 5-phospho-α-D-ribofuranosyl   diphosphate; 1-diphospho-5-phospho-α-D-   -ribofuranose; α-D-ribose 1-diphosphate   5-phosphate	PPRibPd; PRib-PP
4.	Guanosine 2'(or 3')-diphosphate   5'-triphosphate	2'(or 3')-Diphospho-5'-tri-   phosphoguanosine; 2'(or 3')-diphosphoguanylyl   triphosphate	pppGpp; p3Gp2
5.	Guanosine(5')tetra-   phospho(5')guanosine; bis(guanylyl) diphosphate	P1,P4-Bis(5'-guanosyl)   tetraphosphate; bis(5'-guanylyl) diphosphate	G(5')p4(5')G; (ppG)2
6.	7-Methylguanosine(5')tri-   phospho(5')-2'-O-   -methylguanosinee	P1-(7-Methyl-5'-guanosinium-   -5'-yl) P3-(2'-O-methyl-5'-   -guanosyl) triphosphate; 7-methylguanosinium   5'-(2'-O-methylguanosine   5'-triphosphate)	m7G(5')ppp(5')Gm
7.	Uridine(5')diphospho(1)-α-   -D-glucosec	Uridine diphosphate glucose; uridine 5'-(α-D-glucopyranosyl   diphosphate); α-D-glycopyranosyl   5'-uridylyl phosphate	UDP-Glc; U5'pp1Glc; UDPGf
8.	Cytidine(5')diphosphocholinec	Cytidine diphosphate choline; cytidine 5'-(choline   diphosphate); choline (5'-cytidylyl   phosphate)	CDP-choline; CDP-Cho
9.	Adenosine(5')diphospho(5)-β-   -D-ribosec,g	Adenosine diphosphate   ribose; adenosine 5'-(β-D-ribose   5-diphosphate)	ADP-Rib; A5'pp5Rib; (Rib5)ppA
10.	2'-(5-Phospho-β-D-ribosyl)adenosine   5'-phosphatec,g	2'-(5-Phospho-β-D-ribofur-   anosyl)adenosine   5'-phosphate; 2'-(5-phospho-β-D-ribofur-   anosyl)-5'-adenylic acid	AMP(P-Rib); P-Ado(P-Rib); pA2'(pRib); pRib(l-2')pA; iso(ADP-Rib); ψADP-Ribh

^a The symbol Rib for the ribose residue is defined in ref 3. Other symbols are defined in ref 9, especially P or p = phosphoric residue.

^b Triphosphates are treated similarly. Analogs of ATP are further delineated in Table 6. Other nucleoside terms may replace "adenosine," "adenylyl," and "Ado" (ref 9).

^c Locants and descriptors are custoinarily omitted for the isomers shown, so that the terms may be written as, e.g., phosphoribosyl diphosphate, uridinediphosphoglucose (compound 7).

^d The abbreviation PPRP is seen often in the literature; it is not recommended.

^e Bis(nucleotides) of this type, including the methylation as shown, appear to be the common 5'-terminus of many, if not all, of the RNAs of RNA-containing viruses. The use of 7-methyl guanosine instead of the more correct 7-methyl-7-guanosinium is common.

^f Common, but can be ambiguous in context with galactose. Glc for glucose is preferred.

^g Cleavage of "poly(ADP-Rib)" at the 2' linkage of the adenosine moieties gives compound 9, and between the phosphoric residues gives compound 10. Although compound 10 is not an oligophosphoric ester and does not really belong in this table, it is included because it is most often encountered in conjunction with the isomeric compound 9.

^h Disfavored; given here because of occurrence in the literature. (ψ has other meanings in this context.)

Table 3. Representative bisnucleoside phosphates and cyclic phosphates (ref 3, 9).

	Recommended namea	Other nameb	Abbreviations	General structurec
1.	Adenylyl (3'-5')cytidine	Cytidylyl(5'3')adenosine	A-C; Ado-3'P5'-Cyd
2.	Adenylyl(3'-5')cytidine   3'-phosphate	3'-Phosphocytidylyl(5'3')adenosine	A-Cp; Ado-3'P5'-CydP
3.	5'-Phosphoadenylyl(3'-5')cytidine   3'-phosphate	3'-Phosphocytidylyl(5'3')adenosine   5'-phosphate	pA-Cp; PAdo-3'P5'-CydP
4.	5'-Phosphodeoxyadenylyl(3'-5')-   thymidined	Thymidylyl(5'3')deoxyadenosine   5'-phosphate	pdA-dT; d(pA-T); P-dAdo-3'P5'-dThd
5.	5'-Triphosphoguanylyl(3'-5')cytidine	Cytidyly1(5'3')guanosine   5'-triphosphate	pppG-C
6.	Cytidine 2',3'-phosphate	Cytidine 2'3'-(cyclic)phosphatee	Cyd>P; Cyd-2',3'-P; C>p
7.	Adenosine 3',5'-phosphate	Adenosine 3',5'-(cyclic)phosphatee	Cyclic AMP; cAMP; Ado-3',5'-P

^a The infix (3'-5') may be omitted if no ambiguity may arise.

^b Many other names, including permutations of those given, are possible, e.g., adenosine(3')-phospho(5')cytidine and 5'-(3'-adenyiyl)cytidine for compound 1.

^c General structure for entries 1-5: R = OH in entries 1, 2, 3, and 5; H in 4. R' = H in 1, 4, and 5; P in 2 and 3. R" = Hin 1 and 2; P in 3 and 4; POPOP in 5.

^d The prefix "ribo" precedes "thymidine" when 5-methyluridine is meant. The symbols Thd and T indicate the latter; dThd and dT represent thymidine (ref 3, 9).

^e "(Cyclic)" is redundant when locants are given in compounds 6 and 7, but is helpful. It is necessary when, in repeated usage, the locants are omitted.

Table 4. Representative phospholipids (involving diesterified phosphoric acid)

	Recommended namea,b	Other names	Abbreviationsc	Structure
1.	sn-Glycero(3)phosphocholine	Glycerol choline phosphate	GroPCho
2.	(3-sn-Phosphatidyl)choline	1,2-Diacyl-sn-glycero(3)phosphocholine; lecithind	PtdCho; acyl2GroPCho
3.	(3-sn-Phosphatidyl)-L-serine	1,2-Diacyl-sn-glycero(3)-L-phosphoserine; cephalind	PtdSer; acyl2GroPSer
4.	(3-sn-Phosphatidyl)ethanolamine	1,2-Diacyl-sn-glycero(3)phospho-   ethanolamine; cephalind	PtdEtn; acyl2GroPEtn
5.	2-Acyl-1-(1-alkenyl)-sn-   glycero(3)phosphocholine	Plasmenylcholinee; plasmalogen
6.	1-(3-sn-Phosphatidyl)-sn-   glycerol	1,2-Diacyl-sn-glycero(3)phospho(1)-sn-   -glycerol	PtdGro
7.	1-(3-sn-Phosphatidyl)-D-myo-   inositol	1,2-Diacyl-sn-glycero(3)phospho(1)-D-myo-   inositol; phosphoinositided	PtdIns
8.	1-(3-sn-Phosphatidyl)-D-myo-   inositol 4-phosphate	1,2-Diacyl-sn-glycero(3)phospho(1)-D-myo-   inositol 4-phosphate; 1,2-diacyl-sn-glycero(3)phospho(1)-4-   -phospho-D-myo-inositol; phosphoinositide 4-phosphated; diphosphoinositided	PtdIns4P; PtdIns-4-P
9.	1-(3-sn-Phosphatidyl)-D-myo-   inesitol 4,5-bis(phosphate)	1,2-Diacyl-sn-glycero(3)phospho(1)-D-myo-   inositol 4,5-bis(phosphate); 1,2-diacyl-sn-glycero(3)-phospho(1)-4,5-bis-   (phospho)-D-myo-inositol; phosphoinositide 4,5-bis(phosphate)d; triphosphoinositided	PtdIns(4,5)P2; PtdIns-4,5-P2
10.	sn-Glycero(3)-2-   -phosphonoethylaminef	sn-Glycerol 3-[(2-aminoethyl)phosphonate]	GroPEtNH2
11.	(3-sn-Phosphatidyl)ethylaminef	1,2-Diacyl-sn-glycero(3)-2-   -phosphonoethylamine	PtdEtNH2

^a Stereospecific numbering denoted by sn is defined in ref 8. If fully defined in a paper, sn and various locants and descriptors may be omitted from the recommended names and abbreviations. The infix "phospho" replaces "phosphoryl" and "phosphinico," which have been used in the past (ref 2, 3) (see Sections 1 and 4 of the text).

^b Phosphatidyl = 1,2-diacyl-sn-glycero(3)phospho, which may replace it when desired. For O-alkenyl- and O-alkyl-substituted glycero compounds ("lyso" compounds), see entry 5 and ref 5.

^c The symbols Ptd for phosphatidyl, Gro for glycerol, Cho for choline, Ser for serine, Etn for othanolamine, Ins for inositol, and P for a phosphoric residue are defined in ref 5.

^d Trivial names occasionally used in the past; not recommended. Included here only for reference.

^e Plasmenyl and plasmanyl are defined in ref 5.

^f Phosphonic derivatives, containing a P-C bond (compare entry 4, also Table 7).

Table 5. Phosphoric amides (phosphoramidic acids or amidophosphoric acids)

	Recommended namesa	Other namesb,c	Structure
1.	Phosphocreatine	Nω-Phosphonocreatine; N-(N-Phosphonoamidino)sarcosine
2.	Phosphoglycocyamine	Nω-Phosphonoglycocyamine; N-phosphonoguanidinoacetic acid; N-(N-phosphonoamidino)glycine
3.	Phosphoguanidine	N-Amidinophosphoramidate; N-amidinophosphoramidic acid
4.	pros-Phosphohistidined; τ-phosphohistidine	3(1)- Phosphonohistidinec
5.	tele-Phosphohistidined; τ-phosphohistidine	1(3)-Phosphonohistidinec

^b The symbol ω is used to mean the NH₂ terminal group.

^c The prefix "phosphonato" may be used to indicate an ionic form (ref 1, Rule 5.52).

^d For definition of pros (π) and tele (τ) locants, see ref 10, 12.

Table 6. Representative phosphoric anhydrides and fluorophosphates^a

Asp(βP)

	Recommended names	Other names	Abbreviations	Structure
1.	Acetyl phosphate	Monoacetyl phosphate; acetic phosphoric monoanhydride	Ac-P	CH3CO2-P
2.	β-Aspartyl phosphate	Mono-β-aspartyl phosphate; β-aspartic phosphoric monoanhydride
3.	Carbamoyl phosphateb	Monocarbamoyl phosphate; carbamic phosphoric monoanhydride	Cbm-P	H2NCO2-P
4.	Adenosine   5'-phosphosulfate	Adenosine 5'-P-phosphatosulfatec; 5'-adenylyl sulfate; 5'-adenytic sulfuric monoanhydride	APSd; AdoPS
5.	Adenosine 3'-phosphate   5'-phosphosulfate; 3'-phosphoadenosine   5'-phosphosulfate	Adenosine 3'-phosphate 5'-P-phosphatosulfatec; 3'-phospho-5'-adenylyl sulfate; 3'-phospho-5'-adenylic sulfuric monoanhydride	PAPSd; PAdoPS
6.	Seryl adenylate	1-O-(5'-Adenylyl)serine; adenosine(5')phospho(1)serine	AMP-Ser; Ser-P-Ado
7.	3-Phosphoglyceroyl   phosphatee	3-O-Phosphonoglyceric phosphoric   monoanhydride; (glyceroyl phosphate) 3-phosphate	Gri(1,3)P2f
8.	Diisopropyl fluorophosphate	Diisopropyl phosphorofluoridate	iPr2P-Fg	[(CH3)2CHO]2P(O)F

^a See Sections 3 and 7 in text.

^b "Carbamyl," which is often used, is not in accord with the Organic Rules (ref 7 Rule 431.2).

^c See Rules of Inorganic Nomenclature (ref 6, Rule 4.211).

^d Commonly used in the literature; Ado form is preferred for A and P and S for the acid residues.

^e See entry 16 in Table 1.

^f See footnote b in Table 1.

^g Equivalent to DIPF, FDIP, DFP, and Dip-F (ref 10).

Table 7. Representative C-phosphonates

	Recommended name	Other namesa	Structure
1.	(2-Aminoethyl)phosphonic acidb	2-Phosphonoethylamine; ciliatine
2.	(2-Oxoethyl)phosphonic acid	(Formyimethyl)phosphonic acid; phosphonoacetaldehyde	P-CH2CHO

^b See also entries 10 and 11 in Table 4.

Table 8. Adenosine 5'-triphosphate analogs^a

Adenosine
  5'-α,β-μ-methylenetri-
  phosphate;
adenosine
  5'-[α,β-methylene]tri-
  phosphate

	Recommended name	Other namesb	Abbreviations	Structure
1.	Adenosine (5'O1)-1,2-μ-   -methylenetriphosphate; adenosine (5'P1)-1,2-μ-   -methylenetriphosphate	AdoP[CH2]PP; pp[CH2]pA
2.	Adenosine   5'-β,γ-μ-imidotri-   phosphate; adenosine   5'-[β,γ-imido]tri-   phosphate	Adenosine (5'O3)-1,2-μ-   -imidotriphosphate; adenosine (5'P3)-1,2-μ-   -imidotriphosphate; 5'-adenylyl imidodiphosphate; 5'-adenylyl iminodiphosphonatec	AdoPP[NH]P; p[NH]ppA
3.	Adenosine   5'-γ-thiotri-   phosphate	Adenosine (5'O3)-1-   -thiotriphosphate; adenosine (5'-P3)-1-   -thiotriphosphate	AdoPPP[S]; [S]pppA; ATP[S]

^a See Section 5 in text.

^b Adaptation of principles of inorganic nomenclature for isopolyanions (ref 6, Rule 4.15).

^c "Iminodiphosphonate", is derived from organic nomenclature principles (ref 7, Rules B-15.1, C-815.1).