Np mrd loader

Record Information
Version1.0
Created at2023-05-05 12:00:10 UTC
Updated at2024-05-11 04:52:26 UTC
NP-MRD IDNP0331610
Secondary Accession NumbersNone
Natural Product Identification
Common Name(−)-versicolamide B
Description(+)-Notoamide B belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. It was first documented in 2015 (PMID: 25767298). Based on a literature review a significant number of articles have been published on (+)-Notoamide B (PMID: 32672903) (PMID: 30016097) (PMID: 29632911) (PMID: 29622844).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC26H29N3O4
Average Mass447.5350 Da
Monoisotopic Mass447.21581 Da
IUPAC Name(1'R,3S,3'R,7'R)-2,13'-dihydroxy-4',4',7,7-tetramethyl-7H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one
Traditional Name(1'R,3S,3'R,7'R)-2,13'-dihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one
CAS Registry NumberNot Available
SMILES
CC1(C)[C@H]2C[C@@]34CCCN3C(=O)[C@]2(C[C@]11C(O)=NC2=C1C=CC1=C2C=CC(C)(C)O1)N=C4O
InChI Identifier
InChI=1S/C26H29N3O4/c1-22(2)10-8-14-16(33-22)7-6-15-18(14)27-20(31)25(15)13-26-17(23(25,3)4)12-24(19(30)28-26)9-5-11-29(24)21(26)32/h6-8,10,17H,5,9,11-13H2,1-4H3,(H,27,31)(H,28,30)/t17-,24-,25+,26-/m1/s1
InChI KeyRNWRZMCJFWSZOX-UVZSNKINSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400, C3D6O, simulated)zhangcuixian@gzucm.edu.cnguangzhou university of Chinese medicinezhangcuixian2024-05-11View Spectrum
Species
Species of Origin
Species NameSourceReference
versicolor CGF 9-1-2
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole or derivatives
  • Indolizidine
  • Alkyl aryl ether
  • Delta-lactam
  • Piperidinone
  • Tetrahydropyridine
  • Piperidine
  • Benzenoid
  • Cyclic carboximidic acid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Ether
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • 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
logP3.59ChemAxon
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)0.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.72 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity124.7 m³·mol⁻¹ChemAxon
Polarizability48.4 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17613213
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16680451
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Gao S, Tian WJ, Liao ZJ, Wang GH, Zeng DQ, Liu XZ, Wang XY, Zhou H, Chen HF, Lin T: Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii. Chem Biodivers. 2020 Sep;17(9):e2000424. doi: 10.1002/cbdv.202000424. Epub 2020 Aug 31. [PubMed:32672903 ]
  2. Li H, Sun W, Deng M, Zhou Q, Wang J, Liu J, Chen C, Qi C, Luo Z, Xue Y, Zhu H, Zhang Y: Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor. J Org Chem. 2018 Aug 3;83(15):8483-8492. doi: 10.1021/acs.joc.8b01087. Epub 2018 Jul 25. [PubMed:30016097 ]
  3. Klas KR, Kato H, Frisvad JC, Yu F, Newmister SA, Fraley AE, Sherman DH, Tsukamoto S, Williams RM: Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi. Nat Prod Rep. 2018 Jun 20;35(6):532-558. doi: 10.1039/c7np00042a. [PubMed:29632911 ]
  4. Sugimoto K, Sadahiro Y, Kagiyama I, Kato H, Sherman DH, Williams RM, Tsukamoto S: Isolation of amoenamide A and five antipodal prenylated alkaloids from Aspergillus amoenus NRRL 35600. Tetrahedron Lett. 2017 Jul 19;58(29):2797-2800. doi: 10.1016/j.tetlet.2017.05.057. Epub 2017 May 18. [PubMed:29622844 ]
  5. Kato H, Nakahara T, Yamaguchi M, Kagiyama I, Finefield JM, Sunderhaus JD, Sherman DH, Williams RM, Tsukamoto S: Bioconversion of 6-epi-Notoamide T Produces Metabolites of Unprecedented Structures in a Marine-derived Aspergillus sp. Tetrahedron Lett. 2015 Jan 1;56(1):247-251. doi: 10.1016/j.tetlet.2014.11.083. [PubMed:25767298 ]
  1. Hu JS, He YP, Zhou FG, Wu PP, Chen LY, Ni C, Zhang ZK, Xiao XJ, An LK, He XX, Zhang CX: New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2. Chem Biodivers. 2023 Jun;20(6):e202300301. doi: 10.1002/cbdv.202300301. Epub 2023 May 17. [PubMed:37097072 ]