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Record Information
Version2.0
Created at2021-06-20 17:37:53 UTC
Updated at2021-06-30 00:03:37 UTC
NP-MRD IDNP0033680
Secondary Accession NumbersNone
Natural Product Identification
Common Namezanthocadinanine A
Provided ByJEOL DatabaseJEOL Logo
DescriptionZanthocadinanine A belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. zanthocadinanine A is found in Zanthoxylum nitidum. zanthocadinanine A was first documented in 2008 (Yang, C. -H., et al.). Based on a literature review very few articles have been published on zanthocadinanine A.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC37H45NO5
Average Mass583.7690 Da
Monoisotopic Mass583.32977 Da
IUPAC Name(20R)-20-{[(4aR,5S,8S,8aR)-5-methoxy-5-methyl-8-(propan-2-yl)-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]methyl}-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14(19),15,17-octaene
Traditional Name(20R)-20-{[(4aR,5S,8S,8aR)-8-isopropyl-5-methoxy-5-methyl-4,4a,6,7,8,8a-hexahydro-3H-naphthalen-2-yl]methyl}-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14(19),15,17-octaene
CAS Registry NumberNot Available
SMILES
[H]C1=C([H])C2=C(C(OC([H])([H])[H])=C1OC([H])([H])[H])[C@]([H])(N(C1=C3C([H])=C4OC([H])([H])OC4=C([H])C3=C([H])C([H])=C21)C([H])([H])[H])C([H])([H])C1=C([H])[C@@]2([H])[C@@]([H])(C([H])([H])C([H])([H])[C@@](OC([H])([H])[H])(C([H])([H])[H])[C@]2([H])C([H])([H])C1([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C37H45NO5/c1-21(2)24-14-15-37(3,41-7)29-12-8-22(16-28(24)29)17-30-34-25(11-13-31(39-5)36(34)40-6)26-10-9-23-18-32-33(43-20-42-32)19-27(23)35(26)38(30)4/h9-11,13,16,18-19,21,24,28-30H,8,12,14-15,17,20H2,1-7H3/t24-,28-,29+,30+,37-/m0/s1
InChI KeyRDACIPRKFVDYFL-XXZQSUMOSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, C6D6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Zanthoxylum nitidumJEOL database
    • Yang, C. -H., et al, J. Nat. Prod. 71, 669 (2008)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassBenzophenanthridine alkaloids
Sub ClassDihydrobenzophenanthridine alkaloids
Direct ParentDihydrobenzophenanthridine alkaloids
Alternative Parents
Substituents
  • Dihydrobenzophenanthridine alkaloid skeleton
  • Cadinane sesquiterpenoid
  • Sesquiterpenoid
  • Benzoquinoline
  • Phenanthridine
  • Naphthalene
  • Quinoline
  • Benzodioxole
  • Anisole
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Organoheterocyclic compound
  • Acetal
  • Azacycle
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen 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
logP7ALOGPS
logP7.55ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)2.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.39 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity171.44 m³·mol⁻¹ChemAxon
Polarizability66.18 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23340708
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44567550
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yang, C. -H., et al. (2008). Yang, C. -H., et al, J. Nat. Prod. 71, 669 (2008) . J. Nat. Prod..