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Record Information
Version2.0
Created at2021-06-20 23:57:18 UTC
Updated at2025-02-11 15:45:51 UTC
NP-MRD IDNP0042246
Natural Product DOIhttps://doi.org/10.57994/0595
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-versicolamide B
Provided ByJEOL DatabaseJEOL Logo
Description(+)-Versicolamide 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. (+)-versicolamide B is found in Aspergillus taichungensis. (+)-versicolamide B was first documented in 2015 (PMID: 25615822). Based on a literature review a small amount of articles have been published on (+)-Versicolamide B (PMID: 32672903) (PMID: 37097072).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC26H29N3O4
Average Mass447.5350 Da
Monoisotopic Mass447.21581 Da
IUPAC Name(1'S,3S,3'R,7'S)-4',4',7,7-tetramethyl-2,7-dihydro-1H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,8',13'-trione
Traditional Name(1'S,3S,3'R,7'S)-4',4',7,7-tetramethyl-1H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,8',13'-trione
CAS Registry NumberNot Available
SMILES
[H]N1C(=O)[C@@]2(C3=C1C1=C(OC(C([H])=C1[H])(C([H])([H])[H])C([H])([H])[H])C([H])=C3[H])C([H])([H])[C@@]13N([H])C(=O)[C@@]4(N(C1=O)C([H])([H])C([H])([H])C4([H])[H])C([H])([H])[C@]3([H])C2(C([H])([H])[H])C([H])([H])[H]
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-XRNKBYASSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
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
Aspergillus taichungensisJEOL database
    • Cai, S., et al, Org. Lett. 15, 2168 (2013)
Aspergillus 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
  • Azaspirodecane
  • Indole or derivatives
  • Dihydroindole
  • Indolizidine
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Alkyl aryl ether
  • Delta-lactam
  • N-alkylpiperazine
  • Piperidinone
  • 1,4-diazinane
  • Benzenoid
  • Piperazine
  • Piperidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen 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
logP2.94ALOGPS
logP2.04ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.74 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity123.42 m³·mol⁻¹ChemAxon
Polarizability48.73 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 ID21447239
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24879784
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. Kato H, Nakahara T, Sugimoto K, Matsuo K, Kagiyama I, Frisvad JC, Sherman DH, Williams RM, Tsukamoto S: Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications. Org Lett. 2015 Feb 6;17(3):700-3. doi: 10.1021/ol5037198. Epub 2015 Jan 23. [PubMed:25615822 ]
  3. 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 ]
  4. Cai, S., et al. (2013). Cai, S., et al, Org. Lett. 15, 2168 (2013). Org. Lett..