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Record Information
Version2.0
Created at2022-09-02 13:54:31 UTC
Updated at2022-09-02 13:54:31 UTC
NP-MRD IDNP0156662
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1e,3z,5z,7s,8r,9s,10s,11s,13r,15s,16z,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazatetracyclo[23.2.1.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,5,16,18,20,26-heptaen-28-one
DescriptionAlteramide A belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. (1e,3z,5z,7s,8r,9s,10s,11s,13r,15s,16z,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazatetracyclo[23.2.1.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,5,16,18,20,26-heptaen-28-one was first documented in 2014 (PMID: 25058318). Based on a literature review a small amount of articles have been published on Alteramide A (PMID: 26200218) (PMID: 30025185) (PMID: 30794487).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H38N2O6
Average Mass510.6310 Da
Monoisotopic Mass510.27299 Da
IUPAC Name(3Z,5Z,7S,8R,9S,10S,11S,13R,15S,16Z,18Z,24S,25S)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazatetracyclo[23.2.1.0^{8,15}.0^{9,13}]octacosa-1,3,5,16,18,20,26-heptaen-28-one
Traditional Name(3Z,5Z,7S,8R,9S,10S,11S,13R,15S,16Z,18Z,24S,25S)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazatetracyclo[23.2.1.0^{8,15}.0^{9,13}]octacosa-1,3,5,16,18,20,26-heptaen-28-one
CAS Registry NumberNot Available
SMILES
CC[C@H]1C[C@@H]2C[C@H]3\C=C/C=C\C(O)=NCC[C@H](O)[C@@H]4N=C(O)\C(C4=O)=C(/O)\C=C/C=C\[C@H](O)[C@H]3[C@@H]2[C@H]1C
InChI Identifier
InChI=1S/C29H38N2O6/c1-3-17-14-19-15-18-8-4-7-11-23(35)30-13-12-22(34)27-28(36)26(29(37)31-27)21(33)10-6-5-9-20(32)25(18)24(19)16(17)2/h4-11,16-20,22,24-25,27,32-34H,3,12-15H2,1-2H3,(H,30,35)(H,31,37)/b8-4-,9-5-,10-6-,11-7-,26-21-/t16-,17-,18+,19+,20-,22-,24+,25-,27-/m0/s1
InChI KeyHZKFYHKCBBWPIX-WJLHUKTPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Monoterpenoid
  • Pyrrolidone
  • 2-pyrrolidone
  • 3-pyrrolidone
  • Pyrrolidine
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Ketone
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Enol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP3.34ALOGPS
logP1.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)6.65ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area142.94 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity146.66 m³·mol⁻¹ChemAxon
Polarizability54.66 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101244493
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Moree WJ, McConnell OJ, Nguyen DD, Sanchez LM, Yang YL, Zhao X, Liu WT, Boudreau PD, Srinivasan J, Atencio L, Ballesteros J, Gavilan RG, Torres-Mendoza D, Guzman HM, Gerwick WH, Gutierrez M, Dorrestein PC: Microbiota of healthy corals are active against fungi in a light-dependent manner. ACS Chem Biol. 2014 Oct 17;9(10):2300-8. doi: 10.1021/cb500432j. Epub 2014 Aug 6. [PubMed:25058318 ]
  2. Xu L, Wu P, Wright SJ, Du L, Wei X: Bioactive Polycyclic Tetramate Macrolactams from Lysobacter enzymogenes and Their Absolute Configurations by Theoretical ECD Calculations. J Nat Prod. 2015 Aug 28;78(8):1841-7. doi: 10.1021/acs.jnatprod.5b00099. Epub 2015 Jul 22. [PubMed:26200218 ]
  3. Ueoka R, Bhushan A, Probst SI, Bray WM, Lokey RS, Linington RG, Piel J: Genome-Based Identification of a Plant-Associated Marine Bacterium as a Rich Natural Product Source. Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14519-14523. doi: 10.1002/anie.201805673. Epub 2018 Aug 23. [PubMed:30025185 ]
  4. Hao L, Zheng X, Wang Y, Li S, Shang C, Xu Y: Inhibition of Tomato Early Blight Disease by Culture Extracts of a Streptomyces puniceus Isolate from Mangrove Soil. Phytopathology. 2019 Jul;109(7):1149-1156. doi: 10.1094/PHYTO-12-18-0444-R. Epub 2019 May 29. [PubMed:30794487 ]
  5. LOTUS database [Link]