1.0 2010-04-08 22:11:25 UTC 2025-11-19 00:49:06 UTC FDB014712 Syringomycin Production by a sugar cane isolate of Pseudomonas syringae pv. syringae Syringomycin is a general name given to a class of lipodepsinonapeptide molecules which are secreted by the plant pathogen Pseudomonas syringae. Lipodepsinonapeptides comprise a closed ring of nine nonribosomally-synthesized amino acids bonded to a fatty acid hydrocarbon tail. A commonly-encountered pathovar (pv) of P. syringae is P. syringae pv syringae which secretes a number of closely-related forms of the molecule. Syringomycins are virulence determinants which means that their secretion is required for the manifestation of disease symptoms on a number of stone fruit crop plants. C53H85ClN14O17 1225.79 1224.590565 (2S)-2-[(3S,6S,9Z,12S,15S,18S,21R,24R,27S)-18,21-bis(2-aminoethyl)-12-benzyl-15-(3-carbamimidamidopropyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-27-{[(3S)-1,3-dihydroxydodecylidene]amino}-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-24-(hydroxymethyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid (S)-[(3S,6S,9Z,12S,15S,18S,21R,24R,27S)-18,21-bis(2-aminoethyl)-12-benzyl-15-(3-carbamimidamidopropyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-27-{[(3S)-1,3-dihydroxydodecylidene]amino}-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-24-(hydroxymethyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl](hydroxy)acetic acid 11140-67-3 [H]C(C)=C1N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C(O)[C@]([H])(CCCNC(N)=N)N=C(O)[C@]([H])(CCN)N=C(O)[C@@]([H])(CCN)N=C(O)[C@@]([H])(CO)N=C(O)[C@]([H])(COC(=O)[C@@]([H])(N=C(O)[C@@]([H])(N=C1O)[C@]([H])(O)C(O)=O)[C@]([H])(O)CCl)N=C(O)C[C@@]([H])(O)CCCCCCCCC InChI=1S/C53H85ClN14O17/c1-3-5-6-7-8-9-13-17-30(70)25-39(72)60-37-28-85-52(84)40(38(71)26-54)67-50(81)41(42(73)51(82)83)68-43(74)31(4-2)61-47(78)35(24-29-15-11-10-12-16-29)65-44(75)32(18-14-23-59-53(57)58)62-45(76)33(19-21-55)63-46(77)34(20-22-56)64-48(79)36(27-69)66-49(37)80/h4,10-12,15-16,30,32-38,40-42,69-71,73H,3,5-9,13-14,17-28,55-56H2,1-2H3,(H,60,72)(H,61,78)(H,62,76)(H,63,77)(H,64,79)(H,65,75)(H,66,80)(H,67,81)(H,68,74)(H,82,83)(H4,57,58,59)/b31-4-/t30-,32-,33-,34+,35-,36+,37-,38+,40-,41-,42-/m0/s1 ZQVJBRJGDVZANE-MXDMHAPNSA-N belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Cyclic depsipeptides Organic compounds Organic acids and derivatives Peptidomimetics Depsipeptides Aromatic heteromonocyclic compounds Alkyl chlorides Alpha amino acid esters Alpha hydroxy acids and derivatives Amino acids Azacyclic compounds Benzene and substituted derivatives Carbonyl compounds Carboximidamides Carboxylic acid esters Carboxylic acids Chlorohydrins Cyclic carboximidic acids Dicarboxylic acids and derivatives Guanidines Hydrocarbon derivatives Imines Lactones Macrolactams Monoalkylamines Organic oxides Organochlorides Organopnictogen compounds Oxacyclic compounds Polyols Primary alcohols Propargyl-type 1,3-dipolar organic compounds Secondary alcohols Alcohol Alkyl chloride Alkyl halide Alpha-amino acid ester Alpha-amino acid or derivatives Alpha-hydroxy acid Amine Amino acid Amino acid or derivatives Aromatic heteromonocyclic compound Azacycle Benzenoid Carbonyl group Carboximidamide Carboximidic acid Carboximidic acid derivative Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Chlorohydrin Cyclic carboximidic acid Cyclic depsipeptide Dicarboxylic acid or derivatives Guanidine Halohydrin Hydrocarbon derivative Hydroxy acid Imine Lactone Macrolactam Monocyclic benzene moiety Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organochloride Organohalogen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Polyol Primary alcohol Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound Secondary alcohol logp 0.14 ALOGPS logs -4.43 ALOGPS solubility 4.58e-02 g/l ALOGPS logp -0.43 ChemAxon pka_strongest_acidic 2.29 ChemAxon pka_strongest_basic 11.91 ChemAxon iupac (2S)-2-[(3S,6S,9Z,12S,15S,18S,21R,24R,27S)-18,21-bis(2-aminoethyl)-12-benzyl-15-(3-carbamimidamidopropyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-27-{[(3S)-1,3-dihydroxydodecylidene]amino}-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-24-(hydroxymethyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid ChemAxon average_mass 1225.79 ChemAxon mono_mass 1224.590565 ChemAxon smiles [H]C(C)=C1N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C(O)[C@]([H])(CCCNC(N)=N)N=C(O)[C@]([H])(CCN)N=C(O)[C@@]([H])(CCN)N=C(O)[C@@]([H])(CO)N=C(O)[C@]([H])(COC(=O)[C@@]([H])(N=C(O)[C@@]([H])(N=C1O)[C@]([H])(O)C(O)=O)[C@]([H])(O)CCl)N=C(O)C[C@@]([H])(O)CCCCCCCCC ChemAxon formula C53H85ClN14O17 ChemAxon inchi InChI=1S/C53H85ClN14O17/c1-3-5-6-7-8-9-13-17-30(70)25-39(72)60-37-28-85-52(84)40(38(71)26-54)67-50(81)41(42(73)51(82)83)68-43(74)31(4-2)61-47(78)35(24-29-15-11-10-12-16-29)65-44(75)32(18-14-23-59-53(57)58)62-45(76)33(19-21-55)63-46(77)34(20-22-56)64-48(79)36(27-69)66-49(37)80/h4,10-12,15-16,30,32-38,40-42,69-71,73H,3,5-9,13-14,17-28,55-56H2,1-2H3,(H,60,72)(H,61,78)(H,62,76)(H,63,77)(H,64,79)(H,65,75)(H,66,80)(H,67,81)(H,68,74)(H,82,83)(H4,57,58,59)/b31-4-/t30-,32-,33-,34+,35-,36+,37-,38+,40-,41-,42-/m0/s1 ChemAxon inchikey ZQVJBRJGDVZANE-MXDMHAPNSA-N ChemAxon polar_surface_area 551.77 ChemAxon refractivity 318.36 ChemAxon polarizability 124.25 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 30 ChemAxon donor_count 19 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1294477 Specdb::MsMs 1294478 Specdb::MsMs 1294479 Specdb::MsMs 1409137 Specdb::MsMs 1409138 Specdb::MsMs 1409139