Np mrd loader

Record Information
Version2.0
Created at2022-04-27 22:24:08 UTC
Updated at2022-04-27 22:24:09 UTC
NP-MRD IDNP0050935
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Amurine
DescriptionAmurine belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (+)-Amurine is found in Elastostema sinuata, Meconopsis cambrica, Papaver auranticum, Papaver kerneri, Papaver nudicaule, Papaver nudicaule var. amurense, Papaver pilosum, Papaver radicatum, Papaver triniifolium, Roemeria refracta and Stephania aculeata. (+)-Amurine was first documented in 2002 (PMID: 12115607). Based on a literature review a small amount of articles have been published on Amurine (PMID: 33039968) (PMID: 17763104) (PMID: 12842145).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H19NO4
Average Mass325.3640 Da
Monoisotopic Mass325.13141 Da
IUPAC Name(1R,12R)-16-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.5.3.0^{1,13}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,13,16-pentaen-15-one
Traditional Name(1R,12R)-16-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.5.3.0^{1,13}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,13,16-pentaen-15-one
CAS Registry NumberNot Available
SMILES
COC1=C[C@]23CCN(C)[C@H](CC4=C2C=C2OCOC2=C4)C3=CC1=O
InChI Identifier
InChI=1S/C19H19NO4/c1-20-4-3-19-9-18(22-2)15(21)7-13(19)14(20)5-11-6-16-17(8-12(11)19)24-10-23-16/h6-9,14H,3-5,10H2,1-2H3/t14-,19-/m1/s1
InChI KeyHTAGIZQYGRLQQX-AUUYWEPGSA-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
Elastostema sinuata-
Meconopsis cambricaLOTUS Database
Papaver auranticumPlant
Papaver kerneriPlant
Papaver nudicauleLOTUS Database
Papaver nudicaule var. amurensePlant
Papaver pilosumLOTUS Database
Papaver radicatumLOTUS Database
Papaver triniifoliumPlant
Roemeria refractaPlant
Stephania aculeataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Benzazocine
  • Isoquinolone
  • Tetralin
  • Benzodioxole
  • Aralkylamine
  • Piperidine
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Cyclic ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • 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
logP1.97ALOGPS
logP1.72ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)7.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.07 m³·mol⁻¹ChemAxon
Polarizability34.49 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 IDC00001802
Chemspider ID4586084
KEGG Compound IDC09334
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462433
PDB IDNot Available
ChEBI ID2689
Good Scents IDNot Available
References
General References
  1. Chen Y, Lu J, Li S, Zhang C, Yang Q, Hu B, Zhou C, Hong J, Jiang G, Yan S: Carnosol attenuates RANKL-induced osteoclastogenesis in vitro and LPS-induced bone loss. Int Immunopharmacol. 2020 Dec;89(Pt A):106978. doi: 10.1016/j.intimp.2020.106978. Epub 2020 Oct 8. [PubMed:33039968 ]
  2. Philipov S, Istatkova R, Yadamsurenghiin GO, Samdan J, Dangaa S: A new 8,14-dihydropromorphinane alkaloid from Papaver nudicaule L. Nat Prod Res. 2007 Jul 20;21(9):852-6. doi: 10.1080/14786410701494777. [PubMed:17763104 ]
  3. Blanchfield JT, Sands DP, Kennard CH, Byriel KA, Kitching W: Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species. Phytochemistry. 2003 Jul;63(6):711-20. doi: 10.1016/s0031-9422(03)00240-1. [PubMed:12842145 ]
  4. Ishikawa S, Nagai S, Sato T, Akadegawa K, Yoneyama H, Zhang YY, Onai N, Matsushima K: Increased circulating CD11b+CD11c+ dendritic cells (DC) in aged BWF1 mice which can be matured by TNF-alpha into BLC/CXCL13-producing DC. Eur J Immunol. 2002 Jul;32(7):1881-7. doi: 10.1002/1521-4141(200207)32:7<1881::AID-IMMU1881>3.0.CO;2-Z. [PubMed:12115607 ]