Np mrd loader

Record Information
Version2.0
Created at2022-09-02 22:04:28 UTC
Updated at2022-09-02 22:04:28 UTC
NP-MRD IDNP0163434
Secondary Accession NumbersNone
Natural Product Identification
Common Namebassianolide
DescriptionBassianolide, also known as BASS, 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. Bassianolide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. bassianolide was first documented in 2018 (PMID: 30029532). Based on a literature review a significant number of articles have been published on bassianolide (PMID: 33058930) (PMID: 34512581) (PMID: 33451141) (PMID: 33166889) (PMID: 33053646) (PMID: 31715183).
Structure
Thumb
Synonyms
ValueSource
(-)-BassianolideChEBI
BASSChEBI
Chemical FormulaC48H84N4O12
Average Mass909.2160 Da
Monoisotopic Mass908.60857 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC(C)C[C@@H]1N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C
InChI Identifier
InChI=1S/C48H84N4O12/c1-25(2)21-33-45(57)61-38(30(11)12)42(54)50(18)35(23-27(5)6)47(59)63-40(32(15)16)44(56)52(20)36(24-28(7)8)48(60)64-39(31(13)14)43(55)51(19)34(22-26(3)4)46(58)62-37(29(9)10)41(53)49(33)17/h25-40H,21-24H2,1-20H3/t33-,34-,35-,36-,37+,38+,39+,40+/m0/s1
InChI KeyQVZZPLDJERFENQ-NKTUOASPSA-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 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Macrolide lactam
  • Tetracarboxylic acid or derivatives
  • Macrolide
  • Macrolactam
  • Alpha-amino acid ester
  • Alpha-amino acid or derivatives
  • Tertiary carboxylic acid amide
  • Lactone
  • Lactam
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP4.64ALOGPS
logS-5.2ALOGPS
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID52084768
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound89254632
PDB IDNot Available
ChEBI ID145108
Good Scents IDNot Available
References
General References
  1. Qasim M, Islam SU, Islam W, Noman A, Khan KA, Hafeez M, Hussain D, Dash CK, Bamisile BS, Akutse KS, Rizwan M, Nisar MS, Jan S, Wang L: Characterization of mycotoxins from entomopathogenic fungi (Cordyceps fumosorosea) and their toxic effects to the development of asian citrus psyllid reared on healthy and diseased citrus plants. Toxicon. 2020 Dec;188:39-47. doi: 10.1016/j.toxicon.2020.10.012. Epub 2020 Oct 12. [PubMed:33058930 ]
  2. D'Amato A, Della Sala G, Izzo I, Costabile C, Masuda Y, De Riccardis F: Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides. Molecules. 2018 Jul 19;23(7). pii: molecules23071779. doi: 10.3390/molecules23071779. [PubMed:30029532 ]
  3. Wang H, Peng H, Li W, Cheng P, Gong M: The Toxins of Beauveria bassiana and the Strategies to Improve Their Virulence to Insects. Front Microbiol. 2021 Aug 26;12:705343. doi: 10.3389/fmicb.2021.705343. eCollection 2021. [PubMed:34512581 ]
  4. Blaszczyk L, Waskiewicz A, Gromadzka K, Mikolajczak K, Chelkowski J: Sarocladium and Lecanicillium Associated with Maize Seeds and Their Potential to Form Selected Secondary Metabolites. Biomolecules. 2021 Jan 13;11(1):98. doi: 10.3390/biom11010098. [PubMed:33451141 ]
  5. Li Y, He N, Luo M, Hong B, Xie Y: Application of untargeted tandem mass spectrometry with molecular networking for detection of enniatins and beauvericins from complex samples. J Chromatogr A. 2020 Dec 20;1634:461626. doi: 10.1016/j.chroma.2020.461626. Epub 2020 Oct 22. [PubMed:33166889 ]
  6. Baldiviezo LV, Pedrini N, Santana M, Mannino MC, Nieva LB, Gentile A, Cardozo RM: Isolation of Beauveria bassiana from the Chagas Disease Vector Triatoma infestans in the Gran Chaco Region of Argentina: Assessment of Gene Expression during Host-Pathogen Interaction. J Fungi (Basel). 2020 Oct 12;6(4):219. doi: 10.3390/jof6040219. [PubMed:33053646 ]
  7. Cheong PCH, Glare TR, Rostas M, Haines S, Brookes JJ, Ford S: Lack of involvement of chitinase in direct toxicity of Beauveria bassiana cultures to the aphid Myzus persicae. J Invertebr Pathol. 2020 Jan;169:107276. doi: 10.1016/j.jip.2019.107276. Epub 2019 Nov 9. [PubMed:31715183 ]
  8. Xu F, Butler R, May K, Rexhepaj M, Yu D, Zi J, Chen Y, Liang Y, Zeng J, Hevel J, Zhan J: Modified substrate specificity of a methyltransferase domain by protein insertion into an adenylation domain of the bassianolide synthetase. J Biol Eng. 2019 Jul 31;13:65. doi: 10.1186/s13036-019-0195-y. eCollection 2019. [PubMed:31388353 ]
  9. Keppanan R, Sivaperumal S, Hussain M, Dash CK, Bamisile BS, Qasim M, Wang L: Corrigendum to "Investigation and molecular docking studies of Bassianolide from Lecanicillium lecanii against Plutella xylostella (Lepidoptera: Plutellidae)" [Comp. Biochem. Physiol. C 206-207 (2018) 65-72]. Comp Biochem Physiol C Toxicol Pharmacol. 2018 Nov;213:62-63. doi: 10.1016/j.cbpc.2018.05.011. Epub 2018 Jun 22. [PubMed:29909016 ]
  10. LOTUS database [Link]