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Record Information
Version2.0
Created at2022-04-28 11:02:00 UTC
Updated at2022-04-28 11:02:00 UTC
NP-MRD IDNP0066803
Secondary Accession NumbersNone
Natural Product Identification
Common NameVittatine
DescriptionVittatine belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. Vittatine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Vittatine is found in Amaryllis belladonna, Crinum asiaticum, Crinum bulbispermum, Crinum bulbispermum Milne, Crinum yemense, Eucharis amazonica, Hippeastrum papilio, Hippeastrum puniceum, Hippeastrum vittatum, Hippeastrum vittatum L.'Herr., Hymenocallis littoralis, Hymenocallis rotata, Ismene narcissiflora, Lycoris radiata, Narcissus pseudonarcissus subsp.pseudonarcissus, Nerine sarniensis, Pancratium canariense, Pancratium maritimum, Pancratium sickenbergeri and Zephyranthes citrina. Vittatine was first documented in 2020 (PMID: 30636443). Based on a literature review a small amount of articles have been published on vittatine (PMID: 35483192) (PMID: 35448871) (PMID: 34641567) (PMID: 33801149).
Structure
Thumb
Synonyms
ValueSource
(3beta,5alpha,13beta,19alpha)-1,2-Didehydro-crinan-3-olKegg
(3b,5a,13b,19a)-1,2-Didehydro-crinan-3-olGenerator
(3Β,5α,13β,19α)-1,2-didehydro-crinan-3-olGenerator
Chemical FormulaC16H17NO3
Average Mass271.3160 Da
Monoisotopic Mass271.12084 Da
IUPAC Name(1R,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-15-ol
Traditional Name(1R,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-15-ol
CAS Registry NumberNot Available
SMILES
O[C@H]1C[C@@H]2N3CC[C@@]2(C=C1)C1=CC2=C(OCO2)C=C1C3
InChI Identifier
InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m1/s1
InChI KeyRPAORVSEYNOMBR-RLCCDNCMSA-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
Amaryllis belladonnaLOTUS Database
Crinum asiaticumLOTUS Database
Crinum bulbispermumLOTUS Database
Crinum bulbispermum MilnePlant
Crinum yemensePlant
Eucharis amazonicaLOTUS Database
Hippeastrum papilioLOTUS Database
Hippeastrum puniceumLOTUS Database
Hippeastrum vittatumLOTUS Database
Hippeastrum vittatum L.'Herr.Plant
Hymenocallis littoralisLOTUS Database
Hymenocallis rotataLOTUS Database
Ismene narcissifloraLOTUS Database
Lycoris radiataLOTUS Database
Narcissus pseudonarcissus subsp.pseudonarcissusPlant
Nerine sarniensisLOTUS Database
Pancratium canariensePlant
Pancratium maritimumLOTUS Database
Pancratium sickenbergeriPlant
Zephyranthes citrinaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassCrinine- and Haemanthamine-type amaryllidaceae alkaloids
Direct ParentCrinine- and Haemanthamine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Hemanthamine/crinine alkaloid skeleton
  • Benzoquinoline
  • Phenanthridine
  • Benzazepine
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Indole or derivatives
  • Azepine
  • Aralkylamine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • 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
logP0.89ALOGPS
logP1.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.85ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.15 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings5ChemAxon
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 IDC00024446
Chemspider ID391810
KEGG Compound IDC12193
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443693
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sierra K, de Andrade JP, R Tallini L, Osorio EH, Yanez O, Osorio MI, Oleas NH, Garcia-Beltran O, de S Borges W, Bastida J, Osorio E, Cortes N: In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase. Biomed Pharmacother. 2022 Jun;150:113016. doi: 10.1016/j.biopha.2022.113016. Epub 2022 Apr 25. [PubMed:35483192 ]
  2. Masi M, Di Lecce R, Merindol N, Girard MP, Berthoux L, Desgagne-Penix I, Calabro V, Evidente A: Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum. Toxins (Basel). 2022 Apr 7;14(4). pii: toxins14040262. doi: 10.3390/toxins14040262. [PubMed:35448871 ]
  3. Maafi N, Mamun AA, Jandourek O, Marikova J, Breiterova K, Diepoltova A, Konecna K, Hostalkova A, Hulcova D, Kunes J, Kohelova E, Koutova D, Safratova M, Novakova L, Cahlikova L: Semisynthetic Derivatives of Selected Amaryllidaceae Alkaloids as a New Class of Antimycobacterial Agents. Molecules. 2021 Oct 4;26(19). pii: molecules26196023. doi: 10.3390/molecules26196023. [PubMed:34641567 ]
  4. Atrahimovich D, Harris R, Eitan R, Cohen M, Khatib S: Galantamine Quantity and Alkaloid Profile in the Bulbs of Narcissus tazetta and daffodil cultivars (Amaryllidaceae) Grown in Israel. Metabolites. 2021 Mar 21;11(3). pii: metabo11030185. doi: 10.3390/metabo11030185. [PubMed:33801149 ]
  5. Katoch D, Kumar D, Padwad YS, Singh B, Sharma U: Narciclasine-4-O-beta-D-xylopyranoside, a new narciclasine glycoside from Zephyranthes minuta. Nat Prod Res. 2020 Jan;34(2):233-240. doi: 10.1080/14786419.2018.1527836. Epub 2019 Jan 12. [PubMed:30636443 ]