A heterodetic cyclic peptide is a peptide consisting only of amino-acid residues, but in which the linkages forming the ring are not solely peptide bonds; one or more is an isopeptide, disulfide, ester, or other bond.
| Member | Definition | Role |
|---|
| aglucovancomycin b | A peptide antibiotic that is vancomycin lacking the disaccharide moiety. | vancomycin aglycone zwitterion; vancomycin aglycone |
| anidulafungin | A semisynthetic echinocandin anti-fungal drug. It is active against Aspergillus and Candida species and is used for the treatment of invasive candidiasis. | anidulafungin |
| carbetocin | Oxytocin in which the hydrogen on the phenolic hydroxy group is substituted by methyl, the amino group on the cysteine residue is substituted by hydrogen, and the sulfur of the cysteine residue is replaced by a methylene group. A synthetic carba-analogue of oxytocin, it is used to control bleeding after giving birth. Like oxytocin, it causes contraction of the uterus. | carbetocin |
| chloroorienticin b | A glycopeptide that is isolated from Amycolatopsis orientalis. | chloroorienticin B |
| cigb-300 | A synthetic 25-membered heterodetic cyclic peptide consisting of a 14-membered linear component attached to an 11-membered cyclic portion. A CK2 inhibitor with potential antineoplastic activity. | CIGB-300 |
| complestatin | A heterodetic cyclic peptide consisting of N-acylated trytophan, 3,5-dichloro-4-hydroxyphenylglycine, 4-hydroxyphenylglycine, 3,5-dichloro-4-hydroxyphenylglycyl, tyrosine and 4-hydroxyphenylglycine residues joined in sequence and in which the side-chain of the central 4-hydroxyphenylglycine residue is attached to the side-chain of the tryptophan via a C3-C6 bond and to the side-chain of the tyrosine via an ether bond from C5. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity. | chloropeptin II; isocomplestatin |
| complestatin | A heterodetic cyclic peptide which is a atropisomer of complestatin. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity. | chloropeptin II; isocomplestatin |
| deamino arginine vasopressin | A synthetic analogue of vasopressin in which 3-mercaptopropionic acid replaces the cysteine residue at position 1 and D-arginine replaces the residue at position 8. An antidiuretic, it increases urine concentration and decreases urine production, and is used (usually as the trihydrate of the acetic acid salt) to prevent and control excessive thirst, urination, and dehydration caused by injury, surgery, and certain medical conditions. It is also used in the diagnosis and treatment of cranial diabetes insipidus and in tests of renal function. | desmopressin |
| deaminooxytocin | A heterodetic cyclic peptide that is the synthetic analog of the peptide hormone oxytocin where the free amino group in the half-cystine residue is replaced by hydrogen. The mechanism of action and pharmacological properties of demoxytocin and oxytocin are similar. The drug affects the permeability of the cell membrane, increasing the content of calcium ions in smooth muscle cells, thereby increasing its contraction. It stimulates the contraction of smooth muscles of the uterus, as well as stimulating the contraction of myoepithelial cells of the mammary gland, and enhances the secretion of milk. | demoxytocin |
| duramycin | A 19-membered heterodetic cyclic peptide that is isolated from Streptoverticillium cinnamoneus. It exhibits antiproliferative properties and induces apoptosis in tumour cells and has been used for treatment of cystic fibrosis. | lancovutide |
| enkephalin, d-penicillamine (2,5)- | A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond. | DPDPE |
| felypressin | A synthetic nonapeptide comprising cysteinyl, phenylalanyl, phenylalanyl, glutaminyl, asparaginyl, cysteinyl, prolyl, lysyl, and glycinamide residues in sequence, with a disulfide bridge joining the two cysteine residues. Its antidiuretic effects are less than those of vasopressin. It is used as a vasoconstrictor in local anaesthetic injections for dental use, and is an ingredient of preparations that have been used for treatment of pain and inflammation of the mouth. | felypressin |
| lanthiopeptin | A type B lantibiotic consisting of a 19 amino acid tetracyclic polypeptide produced by Streptomyces cinnamoneus. | cinnamycin |
| ly-146032 | A polypeptide comprising N-decanoyltryptophan, asparagine, aspartic acid, threonine, glycine, ornithine, aspartic acid, D-alanine, aspartic acid, glycine, D-serine, threo-3-methylglutamic acid and 3-anthraniloylalanine (also known as kynurinine) coupled in sequence and lactonised by condensation of the carboxylic acid group of the 3-anthraniloylalanine with the alcohol group of the threonine residue. | daptomycin |
| neuroprotectin a | A heterodetic cyclic peptide that is chloropeptin II in which the indole moiety is oxidised to the corresponding 2-oxindole. It is a HIV-1 integrase inhibitor isolated from Streptomyces. | complestatin A |
| oxytocin | A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour. | oxytocin |
| prosomatostatin | A heterodetic cyclic peptide consisting of somatostatin in which the amino terminus has been acylated by the fourteen membered peptide Ser-Ala-Asn-Ser-Asn-Pro-Ala-Met-Ala-Pro-Arg-Glu-Arg-Lys. | somatostatin-28 |
| ristocetin | A heterodetic cyclic peptide that is produced by species of Amycolatopsis and Nocardia. | ristocetin |
| salmon calcitonin | A 32-membered heterodetic cyclic peptide comprising the sequence Cys-Ser-Asn-Leu-Ser-Thr-Cys-Val-Leu-Gly-Lys-Leu-Ser-Gln-Glu-Leu-His-Lys-Leu-Gln-Thr-Tyr-Pro-Arg-Thr-Asn-Thr-Gly-Ser-Gly-Thr-Pro-NH2 cyclised by a disulfide bridge between the two Cys residues at positions 1 and 7. | calcitonin |
| somatostatin | A fourteen-membered heterodetic cyclic peptide comprising the sequence Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys cyclised by a disulfide bridge between the two Cys residues at positions 3 and 14. | somatostatin |
| thiazomycin | A heterodetic cyclic peptide isolated from Amycolatopsis fastidiosa. | thiazomycin |
| ustiloxin b | A heterodetic cyclic peptide with formula C26H39N5O12S produced by Ustilaginoidea virens fungi. It is an inhibitor of microtubule assembly. | ustiloxin B |
| viomycin | A cyclic peptide antibiotic produced by the actinomycete Streptomyces puniceus, used in the treatment of tuberculosis. | viomycin |
| ym 216391 | An azamacrocycle with formula C34H32N8O7S isolated from the cultured mycelium of Streptomyces nobilis. It exhibits potent cytotoxic activity against human cancer cell lines. | YM-216391 |