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Record Information
Version2.0
Created at2022-04-28 13:07:00 UTC
Updated at2022-04-28 13:07:00 UTC
NP-MRD IDNP0068112
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-(-)-Nuciferine
DescriptionNuciferine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. D-(-)-Nuciferine is found in Annona cherimola, Annona cherimolia, Artabotrys venustus, Cissampelos pareira , Hexalobus monopetalus, Liriodendron tulipifera, Nelumbo caerulea, Nelumbo nucifera , Paliurus hemsleyanus, Papaver caucasicum, Plumula nelumbensis, Ziziphus jujuba and Zizyphus vulgaris. D-(-)-Nuciferine was first documented in 2021 (PMID: 35003297). Based on a literature review a small amount of articles have been published on Nuciferine (PMID: 35350700) (PMID: 35298888) (PMID: 35167658) (PMID: 35098593).
Structure
Thumb
Synonyms
ValueSource
L-5,6-DimethoxyaporphineMeSH
Nuciferine, (+-)-isomerMeSH
Nuciferine, (S)-isomerMeSH
Chemical FormulaC19H21NO2
Average Mass295.3820 Da
Monoisotopic Mass295.15723 Da
IUPAC Name(9R)-15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaene
Traditional Name(9R)-15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaene
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C2=C3[C@@H](CC4=CC=CC=C24)N(C)CCC3=C1
InChI Identifier
InChI=1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-/m1/s1
InChI KeyORJVQPIHKOARKV-OAHLLOKOSA-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
Annona cherimolaLOTUS Database
Annona cherimoliaPlant
Artabotrys venustusLOTUS Database
Cissampelos pareiraPlant
Hexalobus monopetalusLOTUS Database
Liriodendron tulipiferaLOTUS Database
Nelumbo caeruleaPlant
Nelumbo nuciferaPlant
Paliurus hemsleyanusLOTUS Database
Papaver caucasicumPlant
Plumula nelumbensis-
Ziziphus jujubaLOTUS Database
Zizyphus vulgarisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen 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
logP3.38ALOGPS
logP3.39ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)7.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.95 m³·mol⁻¹ChemAxon
Polarizability33.83 ųChemAxon
Number of Rings4ChemAxon
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 IDC00001905
Chemspider ID9740
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNuciferine
METLIN IDNot Available
PubChem Compound10146
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Xu X, Wang W, Chen Y, Zhang Q, Li B, Zhong Y, Tu Y, Zhang W, Xu G, Jiang L: Simultaneous Determination of Ten Bioactive Components from Shenling Baizhu San in Rat Plasma by UHPLC-MS/MS: Application to a Comparative Pharmacokinetic Study in Normal and Two Models of Ulcerative Colitis Rats. Evid Based Complement Alternat Med. 2021 Dec 29;2021:3518241. doi: 10.1155/2021/3518241. eCollection 2021. [PubMed:35003297 ]
  2. Zheng L, Jiang H, Li R, Song L, Chen R, Dong H: The Pharmacological Mechanisms of Xiaochaihutang in Treating Breast Cancer Based on Network Pharmacology. Contrast Media Mol Imaging. 2022 Mar 9;2022:3900636. doi: 10.1155/2022/3900636. eCollection 2022. [PubMed:35350700 ]
  3. Bai X, Liu X, Li S, An H, Kang X, Guo S: Nuciferine Inhibits TMEM16A in Dietary Adjuvant Therapy for Lung Cancer. J Agric Food Chem. 2022 Mar 30;70(12):3687-3696. doi: 10.1021/acs.jafc.1c08375. Epub 2022 Mar 17. [PubMed:35298888 ]
  4. Wu M, Qi F, Qiu R, Feng J, Ren X, Rong S, Ma H, Pan H, Chang D: Electrochemical Detection of Nuciferine in the Lotus Leaf Based on Efficient Catalysis by Zirconium-MOFs. J AOAC Int. 2022 Jun 29;105(4):1175-1182. doi: 10.1093/jaoacint/qsac024. [PubMed:35167658 ]
  5. Yu X, Chen ML, Liu Y, Li CH, Qiu XL, Ren XL, Wang M, Zhang DQ: An eco-friendly extraction and purification method of nuciferine from Folium nelumbinis with p-sulfonatocalix[6]arenes. Phytochem Anal. 2022 Jun;33(4):543-553. doi: 10.1002/pca.3108. Epub 2022 Jan 31. [PubMed:35098593 ]