Modifications

Modification Abbreviation Peptide Frequency Classification Smile
tetraxetan DOTA Dotatate Gallium Ga 68, Edotreotide gallium Ga-68, Lutetium Lu 177 dotatate 3 A C1CN(CCN(CCN(CCN1CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O
diethylenetriaminepentaacetic acid DTPA Pentetreotide 1 A O=C(O)CN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O
2-aminoethoxy-2-ethoxy acetic acid AEEA Semaglutide 2 P O=C(COCCOCCN)O
(2-aminoethyl)carbamic acid (2-aminoethyl)carbamoyl Pasireotide 1 B NCCNC(O)=O
N-acetyl muramic acid N-AcMur Mifamurtide 1 P C[C@H](C(O)=O)O[C@H]1[C@@H]([C@H](OC([C@@H]1NC(C)=O)O)CO)O
hydrazinecarboxamide NHNHCONH2 Goserelin 1 P NC(NN)=O
2-aminobutane-1,3-diol 2-aminobutane-1,3-diol Pentetreotide, Edotreotide 2 P CC(O)C(N)CO
threoninol Thr-ol Octreotide 1 P CC(C(CO)N)O
2,6-dioxohexahydropyrimidine-4-carboxylic acid 2,6-dioxohexahydropyrimidyl Degarelix 1 P O=C(C[C@@H](C(O)=O)N1)NC1=O
ethane-1,2-diamine diaminoethyl Caspofungin 1 B NCCN
urea ureido Capreomycin, Viomycin, Enviomycin, Degarelix 5 P NC(N)=O
glycinol (ethanolamine) glycinol Gramicidin A 1 P C(CO)N
1-methyl-2,6-dioxohexahydropyrimidine-4-carboxylic acid 1-methyl-2,6-dioxohexahydropyrimidyl Taltirelin 1 P CN1C(C[C@@H](C(O)=O)NC1=O)=O
2-morpholin-4-yl-acetic acid 2-morpholinacetyl Carfilzomib 1 B OC(CN1CCOCC1)=O
2-(1-amino-2-methylbutyl)-4,5-dehydro-1,3-thiazole-4-carbonyl 2-(1-amino-2-methylbutyl)-4,5-dehydro-1,3-thiazole-4-carbonyl Bacitracin 1 B OC([C@@H]1CSC([C@@H](N)[C@H](CC)C)=N1)=O
pyroglutamic acid Pyr Leuprolide, Buserelin, Triptorelin, Goserelin, Gonadorelin, Nafarelin, Histrelin, Protirelin 8 P C1CC(=O)N[C@@H]1C(=O)O
1-methylcyclopropane-1-sulfonamide 1-Me-cyclopropane-1-sulfonamide Voxilaprevir 1 P NS(=O)(C1(C)CC1)=O
cyclopropanesulfonamide cyclopropanesulfonamide Paritaprevir, Grazoprevir 2 P NS(C1CC1)(=O)=O
pyrazine-2-carboxylic acid pyrazinoyl Telaprevir 1 AROM OC(C1=NC=CN=C1)=O
5-methylpyrazine-2-carboxylic acid 5Me-pyrazinoyl Paritaprevir 1 AROM OC(C1=NC=C(C)N=C1)=O
3-amino-4-cyclobutyl-2-oxobutanamide 3-amino-4-cyclobutyl-2-oxobutanamide Boceprevir 1 ALIPH NC(CC1CCC1)C(C(N)=O)=O
deamino cysteine deamino-Cys Eptifibatide, Desmopressin, Atosiban, Betiatide, Demoxytocin 5 P C(CS)C(=O)O
N-(1-amino-2-(1H-indol-3-yl)ethyl)formamide N-(1-amino-2-(1H-indol-3-yl)ethyl)formamide Macimorelin 1 AROM N[C@@H](NC=O)CC1=CNC2=CC=CC=C21
3-amino-N-cyclopropyl-2-oxohexanamide 3-amino-N-cyclopropyl-2-oxohexanamide Telaprevir 1 ALIPH NC(CCC)C(C(NC1CC1)=O)=O
3-hydroxy-7-mercaptohept-4-enoic acid 3-OH-7-mercaptohept-4-enoic acid Romidepsin 1 P OC(CC(O)/C=C/CCS)=O
tert-butylcarbamic acid CONH-tBu Boceprevir 1 ALIPH CC(C)(C)NC(O)=O
butanoic acid butyryl Carbetocin 1 ALIPH O=C(O)CCC
2-amino-4-methyl-1-(2-methyloxiran-2-yl)pentan-1-one 2-amino-4-methyl-1-(2-methyloxiran-2-yl)pentan-1-one Carfilzomib 1 ALIPH NC(CC(C)C)C(C1(OC1)C)=O
2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarbonyl 2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarbonyl Dactinomycin 1 AROM OC(C1=C2C(OC3=C(C)C(C(N)=C(C(O)=O)C3=N2)=O)=C(C)C=C1)=O
3-hexenoic acid 3-hexenoyl Tesamorelin 1 ALIPH CC/C=C/CC(=O)O
tert-butyloxycarbonyl Boc Pentagastrin 1 ALIPH CC(C)(OC(O)=O)C
benzoic acid benzoyl Betiatide 1 AROM OC(C1=CC=CC=C1)=O
ethyl pentanoate ethyl pentanoyl Perindopril 1 ALIPH O=C(CCCC)OCC
4-phenylbutanoic acid 4-phenylbutanoyl Lisinopril 1 A OC(CCCC1=CC=CC=C1)=O
5-methyl-heptanoic acid 5-methyl-heptanoyl Colistin 1 ALIPH CCC(C)CCCC(=O)O
6-methyl-octanoic acid 6-methyl-octanoyl Polymyxin B 1 ALIPH CCC(C)CCCCC(=O)O
ethyl-4-phenylbutanoate ethyl-4-phenylbutanoyl Enalapril, Ramipril, Quinapril, Trandolapril 4 AROM CCOC(CCCC1=CC=CC=C1)=O
phenanthridine phenanthridine Paritaprevir 1 B C12=CC=CC=C1C3=C(C=CC=C3)C=N2
2-(5-(6-methoxyquinoxalin-2-yl)pentyl)cyclopropyl hydrogen carbonate 2-(5-(6-methoxyquinoxalin-2-yl)pentyl)cyclopropyl hydrogen carbonate Grazoprevir 1 AROM OC(OC1C(CCCCCC2=CN=C(C=C(OC)C=C3)C3=N2)C1)=O
2-(5,5-difluoro-5-(6-methoxyquinoxalin-2-yl)pentyl)cyclopropyl hydrogen carbonate Voxilaprevir 1 AROM O=C(O)O[C@@H]1C[C@H]1CCCCC(F)(F)C2=NC3=C(N=C2)C=C(OC)C=C3
decanoic acid Dec Daptomycin 1 ALIPH CCCCCCCCCC(=O)O
4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl-benzoic acid 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl-benzoyl Micafungin 1 AROM CCCCCOC1=CC=C(C=C1)C2=CC(=NO2)C3=CC=C(C=C3)C(=O)O
octadecanedioic acid C18diacid Semaglutide 1 ALIPH O=C(O)CCCCCCCCCCCCCCCCC(O)=O
9,11-dimethyl-tridecanoic acid 9,11-dimethyl-tridecanoyl Caspofungin 1 ALIPH CCC(CC(CCCCCCCCC(O)=O)C)C
4,4'-(1-(4-(tert-butyl)phenyl)pyrrolidine-2,5-diyl)dianiline 4,4'-(1-(4-(tert-butyl)phenyl)pyrrolidine-2,5-diyl)dianiline Ombitasvir 1 AROM NC1=CC=C(C2CCC(C3=CC=C(N)C=C3)N2C4=CC=C(C(C)(C)C)C=C4)C=C1
palmytic acid palmitoyl Liraglutide 1 ALIPH CCCCCCCCCCCCCCCC(=O)O
pentoxyphenyl phenyl benzoic acid pentoxyphenyl phenyl benzoyl Anidulafungin 1 AROM CCCCCOC1=CC=C(C2=CC=C(C3=CC=C(C(O)=O)C=C3)C=C2)C=C1
dipalmitoyl phosphatidyl ethanolamine dipalmitoyl phosphatidyl ethanolamine Mifamurtide 1 ALIPH CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[NH3+])OC(=O)CCCCCCCCCCCCCCC
3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonic acid 3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonyl Argatroban 1 AROM CC1CNC2=C(S(=O)(O)=O)C=CC=C2C1
amine NH2 N.A. N.A. C-TERM ONLY N.A.
aminoethane NHEt Leuprolide, Buserelin, Histrelin N.A. C-TERM ONLY N.A.
methoxyacetyl MeOAc Ombitasvir N.A. N-TERM ONLY N.A.
formyl Formyl Gramicidin N.A. N-TERM ONLY N.A.
acetyl Ac Abarelix N.A. N-TERM ONLY N.A.
-->

Non-natural amino-acids

AMINO ACIDIC RESIDUE Abbreviation Peptide Frequency Classification
4,5-dihydroxy-ornithine 4,5-(OH)2-Orn Anidulafungin, Micafungin 2 B
3-hydroxy-glutamine 3-OH-Gln Micafungin 1 P
4-hydroxy-ornithine 4-OH-Orn Caspofungin 1 B
4-hydroxy-beta-lysine 4-OH-bLys Enviomycin 1 B
2,3-diaminopropionic acid Dap Capreomycin, Viomycin, Enviomycin 6 B
2,4-diaminobutyric acid Dab Colistin, Polymyxin B 12 B
isoglutamine isoGln Mifamurtide (D-isoGln) 1 P
D-citrulline D-Cit Cetrorelix 1 P
3-hydroxyproline 3-Hyp Caspofungin 1 P
hydroxyproline Hyp Icatibant, Pasireotide, Anidulafungin, Caspofungin, Micafungin, Paritaprevir, Grazoprevir 7 P
3-ethyl-hydroxyproline 3-Et-Hyp Voxilaprevir 1 P
5-hydroxy-cyclic arginine 5-OH-cyclic Arg Viomycin 1 B
beta-lysine bLys Capreomycin, Viomycin 3 B
ornithine Orn Daptomycin, Ornipressin, Atosiban, Bacitracin (D-Orn) 4 B
4-methyl-3-hydroxyproline 4-Me-3-Hyp Micafungin, Anidulafungin 2 P
sarcosine Sar Cyclosporine, Dactinomycin 3 ALIF
beta-alanine bAla Pentagastrin 1 ALIF
3,4-dihydroxy-homotyrosine (OH)2-hTyr Caspofungin, Anidulafungin, Micafungin 3 AROM
3-methyl glutamic acid 3-Me-Glu Daptomycin 1 A
homoarginine hArg Eptifibatide 1 B
dehydroalanine Dha Capreomycin, Viomycin, Enviomycin 4 ALIPH
2-aminoisobutyric acid Aib Abaloparatide, Semaglutide, Macimorelin 3 ALIPH
3-(3-pyridyl)-D-alanine D-3Pal Abarelix, Ganirelix, Cetrorelix, Degarelix 4 B
dehydrobutyrine Dhb Romidepsin 1 ALIPH
2-aminobutyric acid Abu Cyclosporine 1 ALIPH
1-amino-2-vinylcyclopropane-1-carboxylic acid 1-amino-2-vinylcyclopropane-1-carboxylic acid Paritaprevir, Grazoprevir 2 ALIPH
1-amino-2-(difluoromethyl)cyclopropane-1-carboxylic acid Voxilaprevir 1 ALIPH
tert-butyl-D-serine D-Ser (tBut) Buserelin, Goserelin 2 ALIPH
6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid Boceprevir 1 ALIPH
N6-isopropyl-lysine Lys(iPr) Abarelix, Degarelix 2 B
p-amino-phenylalanine p-amino-Phe Degarelix 1 B
3,4-dihydroxy-(meta-sulfooxy)homotyrosine (OH)2-hTyr-m-sulfate Micafungin 1 A
2-aminosuberic acid Asu Elcatonin 1 A
kynurenine Kyn Daptomycin 1 B
octahydrocyclopenta[c]pyrrole-1-carboxylic acid octahydrocyclopenta[c]pyrrole-1-carboxylic acid Telaprevir 1 ALIPH
N-methyl-valine N-Me-Val Cyclosporine, Dactinomycin 2 ALIPH
octahydrocyclopenta[b]pyrrole-2-carboxylic acid octahydrocyclopenta[b]pyrrole-2-carboxylic acid Ramipril 1 ALIPH
1-benzyl-D-histidine D-His(1-Bn) Histrelin 1 AROM
tert-butylglycine Tle Telaprevir, Boceprevir, Grazoprevir 3 ALIPH
8,9-diethyl-homoarginine hArg(Et)2 Ganirelix (L- and D-) 2 B
phenylglycine Phg Pasireotide 1 AROM
norleucine Nle Afamelanotide, Bremelanotide 2 ALIPH
3-hydroxy-4-methyl-2-(methylamino)oct-6-enoic acid 3-OH-4-Me-2-(MeNH)oct-6-enoic acid Cyclosporine 1 ALIPH
N-methyl-leucine N-Me-Leu Cyclosporine 4 ALIPH
O-methyl-tyrosine Tyr(Me) Carbetocin 1 AROM
octahydro-1H-indole-2-carboxylic acid Oic Icatibant, Perindopril, Trandolapril 3 ALIPH
beta-2-thienylalanine 2-Thi Icatibant 1 AROM
N-methyl-tyrosine N-Me-Tyr Abarelix 1 AROM
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Tic Icatibant (D), Quinapril 2 AROM
cyclohexylglycine Chg Telaprevir 1 ALIPH
O-ethyl-tyrosine D-Tyr(Et) Atosiban 1 AROM
homophenylalanine hPhe Carfilzomib 1 AROM
tyrosine-O-sufate Tyr (SO3H) Sincalide 1 A
4-Cl-D-phenylalanine D-Phe(4-Cl) Abarelix, Ganirelix, Cetrorelix, Degarelix 4 AROM
2-aminonon-8-enoic acid 2-aminonon-8-enoic acid Paritaprevir 1 ALIPH
2-naphthyl-D-alanine D-2Nal Abarelix, Nafarelin, Lanreotide, Cetrorelix, Ganirelix, Degarelix, Pralmorelin 7 AROM
cyclic arginine cyclic Arg Capreomycin, Enviomycin 3 B
O-benzyl-tyrosine Tyr(Bn) Pasireotide 1 AROM
3-hydroxy-ornithine 3-OH-Orn Caspofungin 1 B
4-methyl-Pipecolic acid 4-Me-Pip Argatroban 1 ALIPH