Np mrd loader

Record Information
Version2.0
Created at2022-04-28 08:23:58 UTC
Updated at2022-04-28 08:23:58 UTC
NP-MRD IDNP0064110
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-Deoxonarchinol A
DescriptionDesoxo-Narchinol A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 7-Deoxonarchinol A is found in Nardostachys chinensis . 7-Deoxonarchinol A was first documented in 2017 (PMID: 28728067). Based on a literature review a significant number of articles have been published on Desoxo-Narchinol A (PMID: 33220358) (PMID: 29202512) (PMID: 30168019) (PMID: 29221883) (PMID: 33976703) (PMID: 31141964).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC12H16O2
Average Mass192.2580 Da
Monoisotopic Mass192.11503 Da
IUPAC Name(4R,4aS,5R)-4-hydroxy-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one
Traditional Name(4R,4aS,5R)-4-hydroxy-4a,5-dimethyl-4,5,6,7-tetrahydronaphthalen-1-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1CCC=C2C(=O)C=C[C@@H](O)[C@@]12C
InChI Identifier
InChI=1S/C12H16O2/c1-8-4-3-5-9-10(13)6-7-11(14)12(8,9)2/h5-8,11,14H,3-4H2,1-2H3/t8-,11-,12+/m1/s1
InChI KeyYWSIMWUTQXMOSD-FXAINCCUSA-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
Nardostachys jatamansiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Secondary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP2.08ALOGPS
logP2.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.2ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity57.12 m³·mol⁻¹ChemAxon
Polarizability20.83 ųChemAxon
Number of Rings2ChemAxon
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 IDC00021035
Chemspider ID28488828
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound56835056
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li R, Wang ZM, Wang Y, Dong X, Zhang LH, Wang T, Zhu Y, Gao XM, Wu HH, Xu YT: Antidepressant activities and regulative effects on serotonin transporter of Nardostachys jatamansi DC. J Ethnopharmacol. 2021 Mar 25;268:113601. doi: 10.1016/j.jep.2020.113601. Epub 2020 Nov 18. [PubMed:33220358 ]
  2. Zhang W, Nan G, Wu HH, Jiang M, Li TX, Wang M, Gao XM, Zhu Y, Song YS, Wang J, Xu YT: A Simple and Rapid UPLC-PDA Method for Quality Control of Nardostachys jatamansi. Planta Med. 2018 May;84(8):536-543. doi: 10.1055/s-0043-123655. Epub 2017 Dec 4. [PubMed:29202512 ]
  3. Kim KW, Yoon CS, Kim YC, Oh H: Desoxo-narchinol A and Narchinol B Isolated from Nardostachys jatamansi Exert Anti-neuroinflammatory Effects by Up-regulating of Nuclear Transcription Factor Erythroid-2-Related Factor 2/Heme Oxygenase-1 Signaling. Neurotox Res. 2019 Jan;35(1):230-243. doi: 10.1007/s12640-018-9951-x. Epub 2018 Aug 31. [PubMed:30168019 ]
  4. Yoon CS, Kim KW, Lee SC, Kim YC, Oh H: Anti-neuroinflammatory effects of sesquiterpenoids isolated from Nardostachys jatamansi. Bioorg Med Chem Lett. 2018 Jan 15;28(2):140-144. doi: 10.1016/j.bmcl.2017.11.041. Epub 2017 Nov 24. [PubMed:29221883 ]
  5. Kim KW, Yoon CS, Park SJ, Bae GS, Kim DG, Kim YC, Oh H: Chemical Analysis of the Ingredients of 20% Aqueous Ethanol Extract of Nardostachys jatamansi through Phytochemical Study and Evaluation of Anti-Neuroinflammatory Component. Evid Based Complement Alternat Med. 2021 Apr 22;2021:5901653. doi: 10.1155/2021/5901653. eCollection 2021. [PubMed:33976703 ]
  6. Thapa SK, Upadhyay M, Kim TH, Shin S, Park SJ, Shin BS: Liquid Chromatography-Tandem Mass Spectrometry of Desoxo-Narchinol a and Its Pharmacokinetics and Oral Bioavailability in Rats and Mice. Molecules. 2019 May 28;24(11):2037. doi: 10.3390/molecules24112037. [PubMed:31141964 ]
  7. Le VNH, Zhao Y, Cho CW, Na M, Quan KT, Kim JH, Hwang SY, Kim SW, Kim KT, Kang JS: Pharmacokinetic study comparing pure desoxo-narchinol A and nardosinonediol with extracts from Nardostachys jatamansi. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Dec 1;1102-1103:152-158. doi: 10.1016/j.jchromb.2018.10.003. Epub 2018 Oct 17. [PubMed:30391729 ]
  8. Le VNH, Khong TQ, Na MK, Kim KT, Kang JS: An optimized HPLC-UV method for quantitatively determining sesquiterpenes in Nardostachyos Radix et Rhizoma. J Pharm Biomed Anal. 2017 Oct 25;145:406-413. doi: 10.1016/j.jpba.2017.06.041. Epub 2017 Jul 8. [PubMed:28728067 ]