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Showing Compound Nisin A (FDB002386)

Record Information
Version1.0
Creation date2010-04-08 22:05:21 UTC
Update date2018-05-28 22:12:42 UTC
Primary IDFDB002386
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNisin A
Description6-amino-2-{[2-({2-[(2-{[2-({2-[({7-[(6-amino-2-{[2-({2-[({21-[(6-amino-2-{[(10-{[(15-{[(2Z)-2-[(2-amino-1-hydroxy-3-methylpentylidene)amino]-1-hydroxybut-2-en-1-ylidene]amino}-12-(butan-2-yl)-5,8,11,14-tetrahydroxy-9-methylidene-6-(2-methylpropyl)-1-thia-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-3-yl)(hydroxy)methylidene]amino}-1,4-dihydroxy-9-methyl-11-oxo-3H,6H,7H,9H,10H,11H,13H,14H,15H,15aH-pyrrolo[2,1-i]1-thia-4,7,10-triazacyclotridecan-6-yl)(hydroxy)methylidene]amino}-1-hydroxyhexylidene)amino]-5,8,11,14,17,20-hexahydroxy-15,22-dimethyl-12-(2-methylpropyl)-9-[2-(methylsulfanyl)ethyl]-1-thia-4,7,10,13,16,19-hexaazacyclodocosa-4,7,10,13,16,19-hexaen-3-yl}(hydroxy)methylidene)amino]-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene}amino)-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxyhexylidene)amino]-3,6,12,15,21-pentahydroxy-14-[(1H-imidazol-5-yl)methyl]-4,8,20-trimethyl-9,19-dithia-2,5,13,16,22-pentaazabicyclo[9.9.2]docosa-2,5,12,15,21-pentaen-17-yl}(hydroxy)methylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-3-(1H-imidazol-5-yl)propylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxyprop-2-en-1-ylidene]amino}hexanoic acid belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. Based on a literature review very few articles have been published on 6-amino-2-{[2-({2-[(2-{[2-({2-[({7-[(6-amino-2-{[2-({2-[({21-[(6-amino-2-{[(10-{[(15-{[(2Z)-2-[(2-amino-1-hydroxy-3-methylpentylidene)amino]-1-hydroxybut-2-en-1-ylidene]amino}-12-(butan-2-yl)-5,8,11,14-tetrahydroxy-9-methylidene-6-(2-methylpropyl)-1-thia-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-3-yl)(hydroxy)methylidene]amino}-1,4-dihydroxy-9-methyl-11-oxo-3H,6H,7H,9H,10H,11H,13H,14H,15H,15aH-pyrrolo[2,1-i]1-thia-4,7,10-triazacyclotridecan-6-yl)(hydroxy)methylidene]amino}-1-hydroxyhexylidene)amino]-5,8,11,14,17,20-hexahydroxy-15,22-dimethyl-12-(2-methylpropyl)-9-[2-(methylsulfanyl)ethyl]-1-thia-4,7,10,13,16,19-hexaazacyclodocosa-4,7,10,13,16,19-hexaen-3-yl}(hydroxy)methylidene)amino]-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene}amino)-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxyhexylidene)amino]-3,6,12,15,21-pentahydroxy-14-[(1H-imidazol-5-yl)methyl]-4,8,20-trimethyl-9,19-dithia-2,5,13,16,22-pentaazabicyclo[9.9.2]docosa-2,5,12,15,21-pentaen-17-yl}(hydroxy)methylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-3-(1H-imidazol-5-yl)propylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxyprop-2-en-1-ylidene]amino}hexanoic acid.
CAS Number1414-45-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.26ALOGPS
logP11.65ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.51ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count76ChemAxon
Hydrogen Donor Count42ChemAxon
Polar Surface Area1326.24 ŲChemAxon
Rotatable Bond Count67ChemAxon
Refractivity874.73 m³·mol⁻¹ChemAxon
Polarizability349.92 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC143H230N42O37S7
IUPAC name6-amino-2-{[2-({2-[(2-{[2-({2-[({7-[(6-amino-2-{[2-({2-[({21-[(6-amino-2-{[(10-{[(15-{[(2Z)-2-[(2-amino-1-hydroxy-3-methylpentylidene)amino]-1-hydroxybut-2-en-1-ylidene]amino}-12-(butan-2-yl)-5,8,11,14-tetrahydroxy-9-methylidene-6-(2-methylpropyl)-1-thia-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-3-yl)(hydroxy)methylidene]amino}-1,4-dihydroxy-9-methyl-11-oxo-3H,6H,7H,9H,10H,11H,13H,14H,15H,15aH-pyrrolo[2,1-i]1-thia-4,7,10-triazacyclotridecan-6-yl)(hydroxy)methylidene]amino}-1-hydroxyhexylidene)amino]-5,8,11,14,17,20-hexahydroxy-15,22-dimethyl-12-(2-methylpropyl)-9-[2-(methylsulfanyl)ethyl]-1-thia-4,7,10,13,16,19-hexaazacyclodocosa-4,7,10,13,16,19-hexaen-3-yl}(hydroxy)methylidene)amino]-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene}amino)-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxyhexylidene)amino]-3,6,12,15,21-pentahydroxy-14-[(1H-imidazol-5-yl)methyl]-4,8,20-trimethyl-9,19-dithia-2,5,13,16,22-pentaazabicyclo[9.9.2]docosa-2,5,12,15,21-pentaen-17-yl}(hydroxy)methylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-3-(1H-imidazol-5-yl)propylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxyprop-2-en-1-ylidene]amino}hexanoic acid
InChI IdentifierInChI=1S/C143H230N42O37S7/c1-24-69(11)105(148)135(213)162-82(27-4)118(196)174-94-58-225-59-95(175-123(201)89(48-67(7)8)169-115(193)74(16)158-138(216)107(70(12)25-2)180-132(94)210)133(211)184-112-79(21)229-61-96(160-104(190)56-152-134(212)100-38-34-44-185(100)142(112)220)128(206)164-84(36-29-32-42-145)120(198)182-109-76(18)226-60-97(161-103(189)55-151-117(195)85(39-45-223-22)165-122(200)88(47-66(5)6)168-113(191)72(14)156-102(188)54-153-136(109)214)129(207)171-92(51-101(147)187)125(203)166-86(40-46-224-23)119(197)163-83(35-28-31-41-144)121(199)183-110-77(19)228-63-99-130(208)170-90(49-80-52-149-64-154-80)124(202)176-98(62-227-78(20)111(141(219)177-99)181-116(194)75(17)159-140(110)218)131(209)173-93(57-186)127(205)179-108(71(13)26-3)139(217)172-91(50-81-53-150-65-155-81)126(204)178-106(68(9)10)137(215)157-73(15)114(192)167-87(143(221)222)37-30-33-43-146/h27,52-53,64-72,75-79,83-100,105-112,186H,15-16,24-26,28-51,54-63,144-146,148H2,1-14,17-23H3,(H2,147,187)(H,149,154)(H,150,155)(H,151,195)(H,152,212)(H,153,214)(H,156,188)(H,157,215)(H,158,216)(H,159,218)(H,160,190)(H,161,189)(H,162,213)(H,163,197)(H,164,206)(H,165,200)(H,166,203)(H,167,192)(H,168,191)(H,169,193)(H,170,208)(H,171,207)(H,172,217)(H,173,209)(H,174,196)(H,175,201)(H,176,202)(H,177,219)(H,178,204)(H,179,205)(H,180,210)(H,181,194)(H,182,198)(H,183,199)(H,184,211)(H,221,222)/b82-27-
InChI KeyNVNLLIYOARQCIX-GSJOZIGCSA-N
Isomeric SMILES[H]\C(C)=C(\N=C(O)C(N)C(C)CC)C(O)=NC1CSCC(N=C(O)C(CC(C)C)N=C(O)C(=C)N=C(O)C(N=C1O)C(C)CC)C(O)=NC1C(C)SCC(N=C(O)CN=C(O)C2CCCN2C1=O)C(O)=NC(CCCCN)C(O)=NC1C(C)SCC(N=C(O)CN=C(O)C(CCSC)N=C(O)C(CC(C)C)N=C(O)C(C)N=C(O)CN=C1O)C(O)=NC(CC(O)=N)C(O)=NC(CCSC)C(O)=NC(CCCCN)C(O)=NC1C(C)SCC2N=C(O)C(N=C(O)C(C)N=C1O)C(C)SCC(N=C(O)C(CC1=CN=CN1)N=C2O)C(O)=NC(CO)C(O)=NC(C(C)CC)C(O)=NC(CC1=CN=CN1)C(O)=NC(C(C)C)C(O)=NC(=C)C(O)=NC(CCCCN)C(O)=O
Average Molecular Weight3354.09
Monoisotopic Molecular Weight3351.545204732
Classification
Description Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Macrolactam
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Imidazolyl carboxylic acid derivative
  • Amino fatty acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Heterocyclic fatty acid
  • Fatty acyl
  • Azole
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Cyclic carboximidic acid
  • Imidazole
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Lactam
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Primary amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary alcohol
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0219000000-f315c7beaa423c2e8c6a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-7698000100-a1d5a9994d8053b77c132021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-9332101400-439ec229ba4d1d53abdd2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID16133879
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCKZ60-Y:CKZ60-Y
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNisin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference