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Record Information
Version1.0
Created at2020-09-23 01:57:19 UTC
Updated at2021-08-10 02:55:24 UTC
NP-MRD IDNP0001580
Secondary Accession NumbersNone
Natural Product Identification
Common NameZelcovamycin
Provided ByNPAtlasNPAtlas Logo
Description(16Z)-7-acetyl-13-ethyl-16-ethylidene-2,5,8,11,14,20-hexahydroxy-4-[(7-methoxy-1H-indol-3-yl)methyl]-7,18,22-trimethyl-24-thia-3,6,9,12,15,18,21,26-octaazabicyclo[21.2.1]Hexacosa-1(25),2,5,8,11,14,20,23(26)-octaen-17-one belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Zelcovamycin is found in Streptomyces. It was first documented in 1999 (PMID: 10092195). Based on a literature review very few articles have been published on (16Z)-7-acetyl-13-ethyl-16-ethylidene-2,5,8,11,14,20-hexahydroxy-4-[(7-methoxy-1H-indol-3-yl)methyl]-7,18,22-trimethyl-24-thia-3,6,9,12,15,18,21,26-octaazabicyclo[21.2.1]Hexacosa-1(25),2,5,8,11,14,20,23(26)-octaen-17-one (PMID: 33216552) (PMID: 32250484).
Structure
Data?1628564124
SynonymsNot Available
Chemical FormulaC36H45N9O9S
Average Mass779.8700 Da
Monoisotopic Mass779.30610 Da
IUPAC Name(4S,7S,13R,16Z,22R)-7-acetyl-13-ethyl-16-ethylidene-4-[(7-methoxy-1H-indol-3-yl)methyl]-7,18,22-trimethyl-24-thia-3,6,9,12,15,18,21,26-octaazabicyclo[21.2.1]hexacosa-1(25),23(26)-diene-2,5,8,11,14,17,20-heptone
Traditional Name(4S,7S,13R,16Z,22R)-7-acetyl-13-ethyl-16-ethylidene-4-[(7-methoxy-1H-indol-3-yl)methyl]-7,18,22-trimethyl-24-thia-3,6,9,12,15,18,21,26-octaazabicyclo[21.2.1]hexacosa-1(25),23(26)-diene-2,5,8,11,14,17,20-heptone
CAS Registry NumberNot Available
SMILES
[H]N1C([H])=C(C2=C([H])C([H])=C([H])C(OC([H])([H])[H])=C12)C([H])([H])[C@]1([H])N([H])C(=O)C2=C([H])SC(=N2)[C@]([H])(N([H])C(=O)C([H])([H])N(C(=O)\C(N([H])C(=O)[C@]([H])(N([H])C(=O)C([H])([H])N([H])C(=O)[C@@](N([H])C1=O)(C(=O)C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[H])=C(/[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C36H45N9O9S/c1-8-22-30(49)41-23(9-2)34(52)45(6)16-28(48)39-18(3)33-43-25(17-55-33)31(50)42-24(13-20-14-37-29-21(20)11-10-12-26(29)54-7)32(51)44-36(5,19(4)46)35(53)38-15-27(47)40-22/h9-12,14,17-18,22,24,37H,8,13,15-16H2,1-7H3,(H,38,53)(H,39,48)(H,40,47)(H,41,49)(H,42,50)(H,44,51)/b23-9-/t18-,22-,24+,36+/m1/s1
InChI KeyVYMRECQGDKKGCJ-AQHIEDMUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
StreptomycesNPAtlas
Species Where Detected
Species NameSourceReference
Streptomyces sp. K96-0670KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Macrolactam
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 2-heteroaryl carboxamide
  • Anisole
  • Phenol ether
  • Thiazolecarboxylic acid or derivatives
  • Alkyl aryl ether
  • Benzenoid
  • Substituted pyrrole
  • Azole
  • Heteroaromatic compound
  • Pyrrole
  • Thiazole
  • Tertiary carboxylic acid amide
  • Lactam
  • Ketone
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.05ALOGPS
logP-1ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)11.16ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area249.89 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity199.47 m³·mol⁻¹ChemAxon
Polarizability80.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA011696
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8570885
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10395445
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tabata N, Tomoda H, Zhang H, Uchida R, Omura S: Zelkovamycin, a new cyclic peptide antibiotic from Streptomyces sp. K96-0670. II. Structure elucidation. J Antibiot (Tokyo). 1999 Jan;52(1):34-9. doi: 10.7164/antibiotics.52.34. [PubMed:10092195 ]
  2. Hao X, Yu J, Wang Y, Connolly JA, Liu Y, Zhang Y, Yu L, Cen S, Goss RJM, Gan M: Zelkovamycins B-E, Cyclic Octapeptides Containing Rare Amino Acid Residues from an Endophytic Kitasatospora sp. Org Lett. 2020 Dec 4;22(23):9346-9350. doi: 10.1021/acs.orglett.0c03565. Epub 2020 Nov 20. [PubMed:33216552 ]
  3. Krahn D, Heilmann G, Vogel FCE, Papadopoulos C, Zweerink S, Kaschani F, Meyer H, Roesch A, Kaiser M: Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family. Chemistry. 2020 Jul 14;26(39):8524-8531. doi: 10.1002/chem.202001577. Epub 2020 Jun 17. [PubMed:32250484 ]