Np mrd loader

Record Information
Version2.0
Created at2022-05-31 16:32:53 UTC
Updated at2022-05-31 16:32:54 UTC
NP-MRD IDNP0137772
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Sophoranol
DescriptionSophoranol, also known as 5-hydroxymatrine, belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton. (+)-Sophoranol is found in Cuscuta chilensis, Sophora flavescens, Sophora jaubertii, Sophora macrocarpa and Sophora tonkinensis. (+)-Sophoranol was first documented in 2007 (PMID: 17370298). Based on a literature review a small amount of articles have been published on Sophoranol (PMID: 32924588) (PMID: 28936848) (PMID: 30209906) (PMID: 26132528).
Structure
Thumb
Synonyms
ValueSource
5-HydroxymatrineKegg
Chemical FormulaC15H24N2O2
Average Mass264.3690 Da
Monoisotopic Mass264.18378 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number3411-37-8
SMILES
[H][C@]12CCCC(=O)N1C[C@]1(O)CCCN3CCC[C@@]2([H])[C@]13[H]
InChI Identifier
InChI=1S/C15H24N2O2/c18-13-6-1-5-12-11-4-2-8-16-9-3-7-15(19,14(11)16)10-17(12)13/h11-12,14,19H,1-10H2/t11-,12-,14-,15-/m1/s1
InChI KeyVQYBAEAOOJBSTR-QHSBEEBCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cuscuta chilensisLOTUS Database
Sophora flavescensLOTUS Database
Sophora jaubertiiLOTUS Database
Sophora macrocarpaLOTUS Database
Sophora tonkinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassLupin alkaloids
Sub ClassMatrine alkaloids
Direct ParentMatrine alkaloids
Alternative Parents
Substituents
  • Matrine
  • Quinolizidinone
  • Diazanaphthalene
  • Naphthyridine
  • Quinolizidine
  • Delta-lactam
  • Piperidinone
  • Piperidine
  • Tertiary carboxylic acid amide
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007761
Chemspider ID10194136
KEGG Compound IDC17069
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12442899
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li JC, Zhang ZJ, Liu D, Jiang MY, Li RT, Li HM: Quinolizidine alkaloids from the roots of Sophora flavescens. Nat Prod Res. 2022 Apr;36(7):1781-1788. doi: 10.1080/14786419.2020.1817011. Epub 2020 Sep 14. [PubMed:32924588 ]
  2. Han FM, Wang LX, Chen Y, Chen LM, Feng WH, Wang JY, Liu DW, You Y, Tong Y: [Simultaneous determination of seven alkaloids and three flavonoids in Sophorae Tonkinensis Radix et Rhizoma by HPLC]. Zhongguo Zhong Yao Za Zhi. 2016 Dec;41(24):4628-4634. doi: 10.4268/cjcmm20162423. [PubMed:28936848 ]
  3. Pan L, Zhang M, Chen HR: [Chemical Constituents of Alkaloids from the Bark of Sophora japonica]. Zhong Yao Cai. 2016 Sep;39(9):2027-9. [PubMed:30209906 ]
  4. Pan QM, Li YH, Hua J, Huang FP, Wang HS, Liang D: Antiviral Matrine-Type Alkaloids from the Rhizomes of Sophora tonkinensis. J Nat Prod. 2015 Jul 24;78(7):1683-8. doi: 10.1021/acs.jnatprod.5b00325. Epub 2015 Jul 1. [PubMed:26132528 ]
  5. Ye G, Zhu HY, Li ZX, Ma CH, Fan MS, Sun ZL, Huang CG: LC-MS characterization of efficacy substances in serum of experimental animals treated with Sophora flavescens extracts. Biomed Chromatogr. 2007 Jun;21(6):655-60. doi: 10.1002/bmc.805. [PubMed:17370298 ]