Proc. Nati. Acad. Sci. USAVol. 74, No. 6, pp. 2222-2230, June 1977Biochemistry

Nomenclature of phosphorus-containing compounds of biochemicalimportance (Recommendations 1976)*

IUPAC-IUB COMMISSION ON BIOCHEMICAL NOMENCLATUREt

The IUPAC Commissions on the Nomenclature of Inorganicand of Organic Chemistry (CNIC and CNOC) have recentlyprovided, in the "D-Rules" (1), recommendations for naminga large number of organic compounds containing phosphorus.Many such compounds are extremely important in biochem-istry and hence in nearly all branches of biology and medicine.Most of the biochemically important ones are esters and/oranhydrides of various phosphorus-containing acids with com-plex organic alcohols and organic acids. Strict application of the"D Rules" (1) to such compounds would result, in many cases,in rather complicated names, and these would be inconvenientfor most biochemists and biologists to use.

However, other systems of nomenclature, in use in the bio-chemical literature, are available (2-5). It is the purpose of thisdocument to define and recommend certain of these for namingorganic phosphorus-containing compounds in biochemical,biological, and medical publications.A general summary and explanation of the principles in-

volved in the nomenclature of biochemically important organicphosphorus compounds is given below. Representative com-pounds and their recommended names, together with thosederived from more systematic nomenclature (4, 6, 7), includingnames formed according to the "D Rules" (1) where appro-priate, are listed in the tables.

1. Phosphoric esters, RO-PO(OH)2, are named as 0-sub-stituted phosphoric acids or as substituted alcohols (Table 1).Thus, choline 0-(dihydrogen phosphate) and 0-phosphono-choline are both appropriate names. The latter may be con-tracted to phosphocholine, but not changed to phosphoryl-choline; "phosphoryl" is defined (ref. 1, Rule 5.66) as OP< andrequires, if used, the naming of all three groups attached to thephosphorus atom. However, "phosphoryl" is retained in derivedterms such as the names of enzymes (e.g., phosphorylase) or ofprocesses (e.g., phosphorylation).Comment. The form 0-phosphono-R stems from two con-

siderations, (i) the definition (ref. 1, Rule 5.51) of phosphonicacid as HPO(OH)2, and (ii) the principle in organic nomen-clature of substitution of another atom or group for a hydrogenatom of a parent molecule, which, in this case, involves thereplacement of the H of an OH group by -P(O)(OH)2, thephosphono group (ref. 1, Rule 5.52).

* Document of the IUPAC-IUB Commission on Biochemical No-menclature (CBN),t approved by IUPAC and IUB in 1976 andpublished by permission of the International Union of Pure andApplied Chemistry (IUPAC) and the International Union of Bio--chemistry (IUB). Comments and suggestions for future revisions ofthis document may be sent to any member of CBN.t Reprints maybe obtained from the National Research Council Office of Bio-chemical Nomenclature (W. E. Cohn, Director), Biology Division,Oak Ridge National Laboratory, P.O. Box Y, Oak Ridge, TN 37830,U.S.A.

t 0. Hoffmann-Ostenhof (Chairman), W. E. Cohn (Secretary), A. E.Braunstein, H. B. F. Dixon, B. L. Horecker, W. B. Jakoby, P. Karlson,W. Klyne, C. Liebecq, and E. C. Webb.

2222

2. Phosphate may be used for "(dihydrogen phosphate),""(disodium phosphate)," etc., (a) if the nature of the counter-ions is not known or is of no importance in the context, or (b)if a mixture of ionic forms (free acid and/or monoanion and/ordianion) is in question. Thus, in most biochemical or biologicalsystems, where the pH is around 7, "glucose phosphate" maybe used in place of "glucose dihydrogen phosphate," the propernames for the protonated form.Comments. (i) Although glucose phosphate is an ester, the

term "phosphate ester" should not be used: "phosphoric ester"is the appropriate generic term. (ii) When "phosphoric" isfollowed by a generic term (e.g., ester, amide, group), the word"acid" need not intervene. Hence, "phosphoric ester" is com-plete and sufficient, and the residue transferred to glucose toform 0-phosphonoglucose (see Section 1 above) is a "phosphoricresidue." (iii) To distinguish choline phosphate (ester) fromcholine phosphate (salt), the former could be written "choline0-phosphate." However, "phosphocholine" is unambiguous.(For N-phosphono compounds, see Section 6.)

3. Phosphoric anhydrides are of two types, (a) those inwhich two or more phosphoric residues are linked by oxygenatoms to yield diphosphates, triphosphates, etc. (e.g., ADP, ATP,etc.; Table 2) and (b) those in which phosphoric acid forms a"mixed anhydride" with a different type of acid (generally acarboxylic acid, e.g., acetic acid) (Table 6). The latter are named(ref. 1, Rule 5.64) as "R-ic phosphoric anhydrides" or as "R-ylphosphates" (e.g., acetic phosphoric anhydride or acetylphosphate).Comments. (i). "Pyro" should not be used for the substituted

phosphoric anhydrides (ref. 6, Rule 4.12) (Table 2), but maybe retained in such terms as inorganic pyrophosphate (ref. 6,Rule 5.213), pyrophosphatase, pyrophosphate-glycerol trans-ferase, and pyrophosphorolysis (2). (Compare Section 1 abovere "phosphoryl".)

(ii) The prefixes di, tri, tetra, etc. should not be used to in-dicate two or more independent phosphoric residues substitutedon different oxygen (or other) atoms in a single compound; theappropriate multiplying prefixes for such compounds are bis,tris, tetrakis, etc. (ref. 1, Rule 5.51; ref. 6, Rules 2.251 and 4.12).For example, "fructose 1,6-diphosphate" could indicate a di-phosphoric residue bridging positions 1 and 6 of fructose; thecommon biochemical substance is correctly named fructose1,6-bis(phosphate) (ref. 3, Rule 4.4).

4. Phosphodiesters (Tables 3 and 4), which involve thebridging group -PO(OH)-, could be named in terms of phos-phinic acid, H2PO(OH), for which the prefix form is phos-phinico (1). However, the use of this prefix, as in ref. 2, presentscomplications in placing the locants for unsymmetrical diesters.Hence, phosphinico is contracted to phospho, which is used asan infix between the names of the two alcohols. Thus, glycer-ophosphocholine is recommended (5) for the well-knownsubstance [previously (8), but incorrectly, called glycerophos-phorylcholine; compare Section 1 above]. This recommendation

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Biochemistry: Commission on Biochemical Nomenclature

also illustrates the convention by which glycerol phPtbmUeiscontracted to glycerophosphate (8), but this should not be donein a context where "glycero" may be confused with the residueof glyceric acid, as in glycerolactone, or with the prefix glyceroused in carbohydrate nomenclature (ref. 4, Rule 9). (For theplacement of locants, see examples in Tables 1 and 4.)Comments. (i) The use of "phosphoryl" in this situation re-

quires an indication in the name that there is one hydroxylgroup remaining on the phosphoric residue, and would thusfurther lengthen the name (see Section 1 above).

(ii) The diacyl derivatives of glycerophosphocholine arecommonly expressed as derivatives of phosphatidic acid (Table4), i.e., diacylglycerophosphocholine phosphatidylcholine(8).

(iii) The trivial names for the acid radicals of nucleotides(Table 3) include the phosphoric residue, hence the latter is notspecified in oligo- or polynucleotide names, e.g., adenylylcy-tidine suffices for Ado-P-Cyd (locants omitted for clarity; cf.ref. 9).

(iv) The so-called cyclic phosphates (Table 3), of whichadenosine 3',5'-phosphate (cyclic AMP or cAMP) is the best-known example, are named in this form rather than in an in-verted form, which would yield 3',5'-phosphoadenosine. Theword "cyclic," often added before "phosphate," is unnecessaryif the locants are given.

(v) The infix "phospho" gives precedent for "diphospho,""triphospho," "tetraphospho," etc. for the doubly esterifiedoligophosphoric acids (Table 2), e.g., uridinediphosphoglucose,adenosinediphosphoribose.

5. Nucleoside Triphosphate Analogs, in which a methylenegroup (-CH2-), an imido group (-NH-), or a sulfur atomreplaces an oxygen atom bridging two phosphorus atoms, couldbe named by an extension of the convention of inorganic no-menclature (ref. 6, Rule 4.15) that employs ,u to indicate abridging group. Thus the compound symbolized as Ado-(5')P[CH2JPP could be named adenosine 5'-(1,2-,u-meth-ylene)triphosphate, and Ado(5')PP[CH2]P might be namedadenosine 5'-(2,3-,u-methylene)triphosphate. However, for the"methylene" part of these names, [a,f-methylene] and [03,y-methylenel are unambiguous, are consistent with the use ofGreek letters as locants in other situations (7), and are thereforerecommended (see Table 8). (The latter compound can betermed 5'-adenylyl methylenediphosphonate, but this namedoes not contain the significant term "triphosphate".)Comments. (i) The use of square brackets here is similar to

their use in amino-acid replacement (11), indicating a re-placement of the normal constituent.

(ii) Although the bridging methylene group in the Ado-(5')PP[CH2]P example should receive priority for numbering,i.e., should be 1,2-,-methylene to accord with inorganic no-menclature (ref. 6, Rule 4.15), this would require an additionalterm (as in Table 8, column 2); it is therefore not suitable in thiscontext, in which it is desirable to give adenosine first consid-eration (i.e., it is always considered to be linked to the a phos-phorus atom).

(iii) A terminal substitution (e.g., sulfur replacing oxygen onP3) might be named adenosine 5'-[3-thiojtriphosphate, butadenosine 5'-y-thioJtriphosphate is recommended (see iiabove).

(iv) The rules of inorganic nomenclature (ref. 6, Table II)specify "imido" as the ligand name for -NH-; it is, in this case,an imide of phosphoric acid, hence "imido" is recommended

forbiochemnical use with "triphosphate" or "diphosphate" (seeTable 8).

(v) The symbol for the nucleoside does not include the 5'-oxygen atom when the rest of the formula is written out in ex-tenso. Thus, Ado(5')P[CH2]P Ado(5')-O-PO(OH)-CH2-P03H2. Such extended representation may be useful for analogssuch as Ado(5')-CH2-PO3H2, a methylene analog of AMP, andAdo(5')-O-PO(OH)-CH2-AsO3H2.

6. Phosphoric amides (Table 5) are named by changing"acid" in the original acid name to "amide" (ref. 1, Rule 5.62).However, when the nitrogenous group supplying the amidemoiety is known by a trivial name and that name is to be re-tained, the phosphoric amide may be named in the samemanner as the esters (see Section 1 above), but not in the formin which "phosphate" is used as a suffix (see Section 2 above);e.g., phosphocreatine (for N-phosphonocreatine), but not"creatine phosphate," because the term "phosphate" meansthat all atoms attached to the phosphorus atom are oxygenatoms.Comment. The contraction "phosphoamide" for phosphoric

amide is often seen, but becomes unwieldy when either theamide or the phosphoric residue is substituted. Such compoundsshould be named as derivatives of phosphoramidic acid (or ofa phosphoramidate), or of amidophosphoric acid (amido-phosphate) [ref. 1, Rules 5.0(e), 5.53(a, b), and 5.61(a, b)].

7. Fluorophosphoric acids, when doubly esterified, becomefluorophosphates or phosphorofluoridates [ref. 1, Rules 5.53(a,b), 5.61(a, b), and 5.0(e)]. Thus, the well-known compound(PriO)2PO-F or iPr2P-F (4) may be called diisopropyl fluoro-phosphate or diisopropyl phosphorofluoridate (see Table 6).

1. "Nomenclature of Organic Chemistry, Section D," IUPAC In-formation Bulletin, Appendix 31, August 1973, pp. 60-86.

2. Enzyme Nomenclature (1972), (Elsevier Scientific PublishingCompany, Amsterdam and New York), [Supplement 1: Biochim.Biophys. Acta 429,1-45 (1976)1.

3. "Abbreviations and Symbols for Chemical Names of SpecialInterest in Biological Chemistry" (1965 Tentative Rules); Bio-chem. J. 101, 1-7 (1966); Biochemistry 5,1445-1453 (1966); andelsewhere.

4. "Nomenclature of Carbohydrates" (1969), Biochemistry 10,3983-4004 (1971); Eur. J. Biochem. 21, 455-477 (1971); andelsewhere.

5. "Nomenclature of Lipids" (1976), Hoppe-Seyler's Z. Physiol.Chem., in press; Lipids 12, 455-468 (1977).

6. IUPAC Nomenclature of Inorganic Chemistry, (1970) (But-terworths, London).

7. IUPAC Nomenclature of Organic Chemistry, Sections A, B, C,(1971) (Butterworths, London).

8. "The Nomenclature of Lipids" (1967), J. Biol. Chem. 242,4845-4849 (1967); and 245, 1511 (1970); and elsewhere. Revision(1976), in press (5).

9. "Abbreviations and Symbols for Nucleic Acids, Polynucleotides,and their Constituents" (1970), Arch. Biochem. Biophys. 145,425-436 (1971); Eur. J. Biochem. 15,203-208 (1970); and else-where.

10. "Symbols for Amino-Acid Derivatives and Peptides" (Recom-mendations 1971), Biochim. Biophys. Acta 263,205-212 (1972);J. Biol. Chem. 247, 977-983 (1972); and elsewhere.

11. "Rules for Naming Synthetic Modfications of Natural Peptides"(Tentative Rules 1966, amended 1972), Biochemistry 6,362-364(1975); and elsewhere.

12. "Nomenclature of (Y-Amino Acids" (Recommendations 1974),Biochemistry 14, 449-462 (1975); Biochem. J. 149,1-16 (1975);and elsewhere.

Proc. Natl. Acad. Sci. USA 74 (1977) 2223

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2228 Biochemistry: Commission on Biochemical Nomenclature

Table 4. Representative phospholipids (involving diesterified phosphoric acid)

Recommended nameab Other names AbbreviationsC Structure

1. sn-Glycero(3)phosphocholine

2. (3-sn-Phosphatidyl)choline

3. (3-sn-Phosphatidyl )-L-serine

4. (3-sn-Phosphatidyl)ethanol-amine

5. 2-Acyl-1-(1-alkenyl)-sn-glycero(3 )phosphocho-line

6. 1-(3-sn-Phosphatidyl )-sn-glycerol

7. 1-(3-sn-Phosphatidyl)-L-myo-inositol

8. 1-(3-sn-Phosphatidyl )-L-myo-inositol 4-phos-phate

9. 1-(3-sn-Phosphatidyl)-L -myo-inositol3,4-bis(phosphate)

10. sn-Glycero(3)-2-phosphonoethylamine f

11. (3-sn-Phosphatidyl )-ethylamine f

Glycerol choline phosphate

1,2-Diacyl-sn-glycero( 3 )phos-phocholine; lecithin d

1,2-Diacyl-sn-glycero(3 )-L-phos-phoserine; cephalind

1 ,2-Diacyl-sn-glycero(3 )phos-phoethanolamine; cephalind

GroPCho

PtdCho;acyl2 GroPCho

PtdSer;acyl2GroPSer

PtdEtn;acyl2GroPEtn

Plasmenylcholine e;plasmalogen

1, 2-Diacyl-sn-glycero(3 )-phospho(1 )-sn-glycerol

1,2-Diacyl-sn-glycero(3 )-phospho( 1 )-L-myo-inositol; phosphoinositided

1,2-Diacyl-sn-glycero(3 )phos-pho(1)-L-myo-inositol 4-phosphate;

1 ,2-diacyl-sn-glycero(3)phos-pho( 1 )-4-phospho-L-myo-inositol;

phosphoinositide 4-phos-phate d; diphosphoinositide d

1,2-Diacyl-sn-glycero(3 )phos-pho(1)-L-myo-inositol 3,4-bis(phosphate);

1,2-diacyl-sn-glycero(3 )-phospho(1 )-3,4-bis(phospho)-L-myo-inositol;

1)hosphoinositide 3,4-bis-(phosphate)d; triphospho-inositide d

sn-Glycerol 3-[ ( 2-aminoethyl )-phosphonate ]

1 ,2-Diacyl-sn-glycero(3 )-2-phosphonoethylamine

PtdGro

'CH.,OH2 1

HO_-CH.1 +

3CH.O-P-OCH2CH2N(CH3),2 1

'CH2O2CR2 I

RCO2mkH31 ~~~~+

3CH.o-P-OCH2CH2N(CH3)3CH202CR

RCO.,-CH NH2

CH20-P-OH2CHCO2H'CH202CR2 1

RCG02'CH

3CHO-P-OCH2CH2NH2'CH2OCH=-CHR21

RCO,_-CH31 ~~~~~+

3CH,O-P-OCH2CH2N(CH3)2ICH202CR 3CH20H21

RCO2.'-CH HC-9OH,13CH.,O-P-OCH2

Ptdlns

PtdIns4P

PtdIns(3,4 )P2

GroPEtNH2

PtdEtNH2

'CH,2OCR21

RCO2b_-CH3 1CHlO-P-O OH OH

OH

HOO-P

1CH202CR21

RCO2m-CH

3CH 0-P-O OHO-P

54

0-P'CHOH21

HO_-CH2

3CHO-P-HCH2CHNH2' CH2O2CR

RCO2 _CH2 1

3CH20-P-CH2CH2NH2

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 omittedfrom the recommended names and abbreviations. The infix "phospho" replaces "phosphoryl" and "phosphinico," which have been used inthe past (refs. 2 and 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 ethanolamine, Ins for inositol, and P for a phosphoricresidue 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).

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

Recommended namesa Other namesbc Structure

1. Phosphocreatine NL- -Phosphonocreatine; NH CH3N-(N-Phosphonoamidino) sarcosine P-NHC-NCHICOH

2. Phosphoglycocyamine NW -Phosphonoglycocyamine; NHNL -phosphonoguanidinoacetic acid; N NN-(N-phosphonoamidino)glycine P-NHCNHCHC0,H

3. Phosphoguanidine N-Amidinophosphoramidate; NHN-amidinophosphoramidic acid P INHCNH,

4. pros-Phosphohistidined; 3(1)-PhosphonohistidineC VNir-phosphohistidine NH

CHXCHCO.,H5. tele-Phosphohistidined; 1(3)-PhosphonohistidineC P

T-phosphohistidine

NH2~N HICHCHCO2H

a See Section 6 of the text for a discussion of the reasons for not using the "phosphate" form of name for the phosphoric amides. P-Creatineand creatine-P are valid for abbreviation purposes, on the assumption that the hyphen indicates a covalent bond; names such as creatinephosphate do not indicate a covalent bond.

b The symbol w 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 (r) and tele (T) locants, see refs. 10 and 12.

Table 6. Representative phosphoric anhydrides and fluorophosphatesa

Recommended names Other names Abbreviations Structure

1. Acetyl phosphate Monoacetyl phosphate; acetic Ac-P CHC0,-Pphosphoric monoanhydride

2. p-Aspartyl phosphate Mono-,B-aspartyl phosphate; Asp(OP) NH2B-aspartic phosphoric Hmonoanhydride a P

3. Carbamoyl phosphateh Monocarbamoyl phosphate; Cbm-P HNCO,-Pcarbamic phosphoricmonoanhydride

4. Adenosine 5'-phosphosulfate Adenosine 5'-P-phosphatosul- AP~d; HOSO-P-OCH, Adefatec; 5'-adenylyl sulfate; AdoPS

5'-adenylic sulfuric monoan-hydride HO OH

5. Adenosine 3'-phosphate 5'- Adenosine 3'-phosphate 5'-P- PAPSd; Aphosphosulfate; phosphatosulfatec; 3'-phos- PAdoPS H P A

3'-phosphoadenosine 5'- pho-5'-adenylyl sulfate;phosphosulfate 3'-phospho-5'-adenylic P-O OH

sulfuric monoanhydride6. Seryl adenylate 1-0-(5'-Adenylyl)serine; AMP-Ser; NH2

adenosine(5' )phospho(1)- Ser-P-Ado Aserine HOCHCHCO2-P-OCH2 0 Ade

*HO OH7. 3-Phosphoglyceroyl phos- 3-0-Phosphonoglyceric phos- Gri(1,3)Pf P OCH2CH(OH)CO,-P

phatee phoric monoanhydride;(glyceroyl phosphate)

3-phosphate8. Diisopropyl fluorophosphate Diisopropyl phosphorofluori- iPr2P-Fg [(CH,),CHojP(O)F

date

a See Sections 3 and 7 in text.b "Carbamyl," which is often used, is not in accord with the Organic Rules (ref. 10, 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).

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Table 7. Representative C-phosphonates

Recommended name Other namesa Structure

1. (2-Aminoethyl)phosphonic acidb 2-Phosphonoethylamine; p H1H2ciliatine

2. (2-Oxoethyl)phosphonic acid (Formylmethyl)phosphonic acid; P-CH2CHOphosphonoacetaldehyde

a The prefix "phosphonato" may be used to indicate an ionic form (ref. 1, Rule 5.52).b See also entries 10 and 11 in Table 4.

Table 8. Adenosine 5'-triphosphate analogsa

Recommended name Other namesb Abbreviations Structure

1. Adenosine 5'-[a,,s-methylene]- Adenosine (5'-0)-1,2-M- AdoP[CH2]PP; 'P A H P OAtriphosphate methylenetriphosphate; pp[CH21pA POP-CH2-P-OCH2 o Ade

adenosine (5'-P')-1,2-,u-methylenetriphosphate HO OH

2. Adenosine 5--[3,'y-imido]- Adenosine (5'-03)-,2-,u- AdoPP[NH]P; 'r a 6'triphosphate imidotriphosphate; p[NH] ppA P NH-POP-OCH2 0 Ade

adenosine (5'-P3)-1,2-,u-imidotriphosphate; HO OH

5'-adenylyl imidodi-phosphate;

5'-adenylyl iminodi-phosphonatec

3. Adenosine 5'-[,y-thio]- Adenosine-(5'-0)-1- AdoPPP[S]; O$PO-POP-0CH, o Adetriphosphate thiotriphosphate; [S]pppA; I / \ dI

adenosine (5'-P3)-1- ATP[S]thiotriphosphate HO OH

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).

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