Np mrd loader

Record Information
Version2.0
Created at2022-04-29 01:37:39 UTC
Updated at2022-04-29 01:37:39 UTC
NP-MRD IDNP0080618
Secondary Accession NumbersNone
Natural Product Identification
Common NameFlustramine C
DescriptionFlustramine C belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Flustramine C is found in Flustra foliacea. Flustramine C was first documented in 2003 (PMID: 14513766). Based on a literature review a small amount of articles have been published on flustramine C (PMID: 32608431) (PMID: 18576686) (PMID: 17217285) (PMID: 15704923).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H19BrN2
Average Mass319.2460 Da
Monoisotopic Mass318.07316 Da
IUPAC Name(3aR)-6-bromo-1-methyl-3a-(2-methylbut-3-en-2-yl)-1H,2H,3H,3aH-pyrrolo[2,3-b]indole
Traditional Name(3aR)-6-bromo-1-methyl-3a-(2-methylbut-3-en-2-yl)-2H,3H-pyrrolo[2,3-b]indole
CAS Registry NumberNot Available
SMILES
CN1CC[C@]2(C3=CC=C(Br)C=C3N=C12)C(C)(C)C=C
InChI Identifier
InChI=1S/C16H19BrN2/c1-5-15(2,3)16-8-9-19(4)14(16)18-13-10-11(17)6-7-12(13)16/h5-7,10H,1,8-9H2,2-4H3/t16-/m1/s1
InChI KeyFAMNDMIFKHXHGO-MRXNPFEDSA-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
Flustra foliacea-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • 3-alkylindole
  • Indole
  • Aryl bromide
  • Aryl halide
  • Imidolactam
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrole
  • Pyrrolidine
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • 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
logP4.83ALOGPS
logP4.06ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)5.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.3 m³·mol⁻¹ChemAxon
Polarizability31.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00026838
Chemspider ID8217175
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10041611
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Melander RJ, Basak AK, Melander C: Natural products as inspiration for the development of bacterial antibiofilm agents. Nat Prod Rep. 2020 Nov 1;37(11):1454-1477. doi: 10.1039/d0np00022a. Epub 2020 Jul 1. [PubMed:32608431 ]
  2. Kawasaki T, Shinada M, Ohzono M, Ogawa A, Terashima R, Sakamoto M: Total synthesis of (+/-)-flustramines A and C, (+/-)-flustramide A, and (-)- and (+)-debromoflustramines A. J Org Chem. 2008 Aug 1;73(15):5959-64. doi: 10.1021/jo800984a. Epub 2008 Jun 25. [PubMed:18576686 ]
  3. Lindel T, Brauchle L, Golz G, Bohrer P: Total synthesis of flustramine C via dimethylallyl rearrangement. Org Lett. 2007 Jan 18;9(2):283-6. doi: 10.1021/ol0627348. [PubMed:17217285 ]
  4. Fuchs JR, Funk RL: Indol-2-one intermediates: mechanistic evidence and synthetic utility. Total syntheses of (+/-)-flustramines A and C. Org Lett. 2005 Feb 17;7(4):677-80. doi: 10.1021/ol047532v. [PubMed:15704923 ]
  5. Sakamoto M, Kawasaki T, Ishii K, Tamura O: [The chemistry of pericyclic reactions and their application to syntheses of heterocyclic compounds]. Yakugaku Zasshi. 2003 Sep;123(9):717-59. doi: 10.1248/yakushi.123.717. [PubMed:14513766 ]