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Record Information
Version2.0
Created at2022-04-27 22:30:37 UTC
Updated at2022-04-27 22:30:37 UTC
NP-MRD IDNP0051070
Secondary Accession NumbersNone
Natural Product Identification
Common NameDendrobine
DescriptionDendrobine belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Dendrobine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Dendrobine is found in Dendrobium chrysanthum, Dendrobium linawianum and Dendrobium nobile . Dendrobine was first documented in 2021 (PMID: 35069479). Based on a literature review a small amount of articles have been published on Dendrobine (PMID: 35417048) (PMID: 35299950) (PMID: 35238089) (PMID: 34975823).
Structure
Thumb
Synonyms
ValueSource
Dendrobine hydrochlorideMeSH
Chemical FormulaC16H25NO2
Average Mass263.3810 Da
Monoisotopic Mass263.18853 Da
IUPAC Name(1S,4S,7S,8R,11R,12R,13S)-2,12-dimethyl-13-(propan-2-yl)-10-oxa-2-azatetracyclo[5.4.1.1^{8,11}.0^{4,12}]tridecan-9-one
Traditional Name(1S,4S,7S,8R,11R,12R,13S)-13-isopropyl-2,12-dimethyl-10-oxa-2-azatetracyclo[5.4.1.1^{8,11}.0^{4,12}]tridecan-9-one
CAS Registry NumberNot Available
SMILES
CC(C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@@H]1CC[C@@H]3CN(C)[C@H]2[C@]13C
InChI Identifier
InChI=1S/C16H25NO2/c1-8(2)11-12-10-6-5-9-7-17(4)14(16(9,10)3)13(11)19-15(12)18/h8-14H,5-7H2,1-4H3/t9-,10+,11+,12-,13-,14-,16+/m1/s1
InChI KeyRYAHJFGVOCZDEI-UFFNCVEVSA-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
Dendrobium chrysanthumLOTUS Database
Dendrobium linawianumLOTUS Database
Dendrobium nobilePlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • Caprolactone
  • Oxepane
  • Gamma butyrolactone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP2.71ALOGPS
logP2.36ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.09 m³·mol⁻¹ChemAxon
Polarizability29.43 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 IDC00001970
Chemspider ID390948
KEGG Compound IDC09943
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDendrobine
METLIN IDNot Available
PubChem Compound442523
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lou D, Xing X, Liang Y: Dendrobine modulates autophagy to alleviate ox-LDL-induced oxidative stress and senescence in HUVECs. Drug Dev Res. 2022 Apr 13. doi: 10.1002/ddr.21937. [PubMed:35417048 ]
  2. Xu Q, Niu SC, Li KL, Zheng PJ, Zhang XJ, Jia Y, Liu Y, Niu YX, Yu LH, Chen DF, Zhang GQ: Chromosome-Scale Assembly of the Dendrobium nobile Genome Provides Insights Into the Molecular Mechanism of the Biosynthesis of the Medicinal Active Ingredient of Dendrobium. Front Genet. 2022 Mar 1;13:844622. doi: 10.3389/fgene.2022.844622. eCollection 2022. [PubMed:35299950 ]
  3. Lu AJ, Jiang Y, Wu J, Tan DP, Qin L, Lu YL, Qian Y, Bai CJ, Yang JY, Ling H, Shi JS, Yang Z, He YQ: Opposite trends of glycosides and alkaloids in Dendrobium nobile of different age based on UPLC-Q/TOF-MS combined with multivariate statistical analyses. Phytochem Anal. 2022 Jun;33(4):619-634. doi: 10.1002/pca.3115. Epub 2022 Mar 2. [PubMed:35238089 ]
  4. Wang SS, Liu JM, Sun J, Huang YT, Jin N, Li MM, Liang YT, Fan B, Wang FZ: Analysis of Endophytic Bacterial Diversity From Different Dendrobium Stems and Discovery of an Endophyte Produced Dendrobine-Type Sesquiterpenoid Alkaloids. Front Microbiol. 2022 Jan 5;12:775665. doi: 10.3389/fmicb.2021.775665. eCollection 2021. [PubMed:35069479 ]
  5. Qian X, Jin H, Chen Z, Dai Q, Sarsaiya S, Qin Y, Jia Q, Jin L, Chen J: Comparative Transcriptome Analysis of Genes Involved in Sesquiterpene Alkaloid Biosynthesis in Trichoderma longibrachiatum MD33 and UN32. Front Microbiol. 2021 Dec 15;12:800125. doi: 10.3389/fmicb.2021.800125. eCollection 2021. [PubMed:34975823 ]