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Record Information
Version2.0
Created at2022-04-29 01:21:17 UTC
Updated at2022-04-29 01:21:17 UTC
NP-MRD IDNP0080317
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Vellosimine
DescriptionVellosimine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Vellosimine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (+)-Vellosimine is found in Alstonia yunnanensis, Rauvolfia verticillata , Rauvolfia serpentina , Rauvolfia verticillata var.hainanensis and Rauwolfia verticillata. (+)-Vellosimine was first documented in 2007 (PMID: 17217288). Based on a literature review a small amount of articles have been published on vellosimine (PMID: 33783073) (PMID: 28812370) (PMID: 25346454) (PMID: 20392128).
Structure
Thumb
Synonyms
ValueSource
(+)-VellosimineChEBI
Chemical FormulaC19H20N2O
Average Mass292.3820 Da
Monoisotopic Mass292.15756 Da
IUPAC Name(1S,12S,13R,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde
Traditional Name(1S,12S,13R,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde
CAS Registry NumberNot Available
SMILES
C\C=C1\CN2[C@H]3CC4=C(NC5=CC=CC=C45)[C@@H]2C[C@@H]1[C@H]3C=O
InChI Identifier
InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15+,17-,18-/m0/s1
InChI KeyMHASSCPGKAMILD-VICVVEARSA-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
Alstonia yunnanensisPlant
Rauvolfia latifronsPlant
Rauvolfia serpentinaPlant
Rauvolfia verticillata var.hainanensisPlant
Rauwolfia verticillataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMacroline alkaloids
Sub ClassNot Available
Direct ParentMacroline alkaloids
Alternative Parents
Substituents
  • Macroline skeleton
  • Sarpagine-skeleton
  • Vobasan skeleton
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Quinuclidine
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.51ALOGPS
logP2.46ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)15.29ChemAxon
pKa (Strongest Basic)5.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area36.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.18 m³·mol⁻¹ChemAxon
Polarizability33.36 ųChemAxon
Number of Rings5ChemAxon
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 IDC00045433
Chemspider ID9441338
KEGG Compound IDC11634
BioCyc IDVELLOSIMINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11266327
PDB IDNot Available
ChEBI ID18057
Good Scents IDNot Available
References
General References
  1. Yang Z, Tan Q, Jiang Y, Yang J, Su X, Qiao Z, Zhou W, He L, Qiu H, Zhang M: Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids. Angew Chem Int Ed Engl. 2021 Jun 1;60(23):13105-13111. doi: 10.1002/anie.202102416. Epub 2021 May 5. [PubMed:33783073 ]
  2. Ebeh Messanga R, Dominique Serge NB, Abouem A Zintchem A, Norbert MNI, Esther Del Florence MN, Patrick Herve BD, Maximilienne Ascension N, Alex De Theodore A, Dieudonne Emmanuel P, Christian G B, Koert U: Rauvolfianine, a new antimycobacterial glyceroglycolipid and other constituents from Rauvolfia caffra. Sond (Apocynaceae). Nat Prod Res. 2018 Aug;32(16):1971-1976. doi: 10.1080/14786419.2017.1356832. Epub 2017 Aug 16. [PubMed:28812370 ]
  3. Kruger S, Gaich T: Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach. Angew Chem Int Ed Engl. 2015 Jan 2;54(1):315-7. doi: 10.1002/anie.201407280. Epub 2014 Oct 24. [PubMed:25346454 ]
  4. Yin W, Kabir MS, Wang Z, Rallapalli SK, Ma J, Cook JM: Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A. J Org Chem. 2010 May 21;75(10):3339-49. doi: 10.1021/jo100279w. [PubMed:20392128 ]
  5. Yin W, Ma J, Rivas FM, Cook JM: First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A. Org Lett. 2007 Jan 18;9(2):295-8. doi: 10.1021/ol062762q. [PubMed:17217288 ]