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Record Information
Version2.0
Created at2022-04-27 22:40:42 UTC
Updated at2022-04-27 22:40:42 UTC
NP-MRD IDNP0051298
Secondary Accession NumbersNone
Natural Product Identification
Common NameImperialine
DescriptionImperialine, also known as fritillarine or peiminine, belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. Imperialine is found in Fritillaria bucharica, Fritillaria cirrhosa , Fritillaria delavayi , Fritillaria imperialis , Fritillaria meleagris, Fritillaria pallidiflora , Fritillaria proylei, Fritillaria przewalskii , Fritillaria raddeana, Fritillaria taipaiensis, Fritillaria thunbergii, Fritillaria tortifolia, Fritillaria unibracteata , Fritillaria ussuriensis , Fritillaria wabuensia, Fritillaria walujewii , Fritillaria yuminensis, Fritillaria yuminensis L., Petilium eduardi, Petilium eduardii, Petilium raddeana and Rhinopetalum bucharicum. Imperialine was first documented in 2019 (PMID: 31763003). Based on a literature review a small amount of articles have been published on Imperialine (PMID: 34802347) (PMID: 34653522) (PMID: 34650616) (PMID: 32281353).
Structure
Thumb
Synonyms
ValueSource
3beta, 20-Dihydroxy-5alpha-cevan-6-oneMeSH
FritillarineMeSH
PeiminineMeSH
Peiminine hydrochloride, (3beta,5alpha,17beta)-isomerMeSH
Peiminine nitrate salt, (3beta,5alpha,17beta)-isomerMeSH
Peiminine, (3beta,5alpha,17beta)-isomerMeSH
Peiminine, (3beta,5alpha,25alpha)-isomerMeSH
SipeimineMeSH
ZhebeinoneMeSH
Chemical FormulaC27H43NO3
Average Mass429.6450 Da
Monoisotopic Mass429.32429 Da
IUPAC Name(1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosan-17-one
Traditional Name(1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosan-17-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CC[C@@H]2N(C1)C[C@H]1[C@@H]3C[C@H]4[C@@H](CC(=O)[C@H]5C[C@@H](O)CC[C@]45C)[C@@H]3CC[C@H]1[C@]2(C)O
InChI Identifier
InChI=1S/C27H43NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21+,22-,23+,25-,26+,27-/m0/s1
InChI KeyIQDIERHFZVCNRZ-LRCDAWNTSA-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
Fritillaria bucharicaLOTUS Database
Fritillaria cirrhosaPlant
Fritillaria delavayiPlant
Fritillaria imperialisPlant
Fritillaria meleagrisPlant
Fritillaria pallidifloraPlant
Fritillaria proyleiPlant
Fritillaria przewalskiiPlant
Fritillaria raddeanaLOTUS Database
Fritillaria taipaiensisPlant
Fritillaria thunbergiiLOTUS Database
Fritillaria tortifoliaLOTUS Database
Fritillaria unibracteataPlant
Fritillaria ussuriensisPlant
Fritillaria wabuensiaPlant
Fritillaria walujewiiPlant
Fritillaria yuminensisLOTUS Database
Fritillaria yuminensis L.Plant
Petilium eduardiPlant
Petilium eduardiiPlant
Petilium raddeanaPlant
Rhinopetalum bucharicumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentCerveratrum-type alkaloids
Alternative Parents
Substituents
  • Cerveratrum-type alkaloid
  • Azasteroid
  • Quinolizidine
  • Alkaloid or derivatives
  • Piperidine
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP3.32ALOGPS
logP3.22ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)14.16ChemAxon
pKa (Strongest Basic)9.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity122.46 m³·mol⁻¹ChemAxon
Polarizability50.94 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002251
Chemspider ID391280
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImperialin
METLIN IDNot Available
PubChem Compound442977
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ablajan N, Zhao B, Wenjuan X, Zhao J, Sagdullaev SS, Guoan Z, Aisa HA: Chemical components of Aconitum barbatum var. puberulum and their cytotoxic and antibacterial activities. Nat Prod Res. 2021 Nov 22:1-4. doi: 10.1080/14786419.2021.2005050. [PubMed:34802347 ]
  2. Shi YH, Huang QW, Zhu SM, Zhou YM, Zhang LJ, Huang WK, Shao JJ, Zhou JL, Zhang WT: Chemical profiling of Fritillariae thunbergii Miq prepared by different processing methods reveals two new quality markers: Zhebeininoside and imperialine-3-beta-D-glucoside. J Ethnopharmacol. 2022 Jan 30;283:114670. doi: 10.1016/j.jep.2021.114670. Epub 2021 Oct 12. [PubMed:34653522 ]
  3. Liu W, Wei L, Kanai Y, He X: Studies on the Incompatibility between Bulbus fritillariae and Radix aconiti praeparata Based on the P-gp. Evid Based Complement Alternat Med. 2021 Oct 5;2021:8351717. doi: 10.1155/2021/8351717. eCollection 2021. [PubMed:34650616 ]
  4. Che P, Liu JS, Qi YD, Qiang TY, Song YC, Wei XP, Liu HT, Zhang BG: [Simultaneous determination of six major isosteroidal alkaloids in Beimu by UPLC-ELSD]. Zhongguo Zhong Yao Za Zhi. 2020 Mar;45(6):1393-1398. doi: 10.19540/j.cnki.cjcmm.20191223.201. [PubMed:32281353 ]
  5. Li CX, Liu YY, Feng HS, Ma SZ: Effect of superfine grinding on the physicochemical properties of bulbs of Fritillaria unibracteata Hsiao et K.C. Hsia powder. Food Sci Nutr. 2019 Sep 13;7(11):3527-3537. doi: 10.1002/fsn3.1203. eCollection 2019 Nov. [PubMed:31763003 ]