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Record Information
Version2.0
Created at2022-04-28 01:17:41 UTC
Updated at2022-04-28 01:17:41 UTC
NP-MRD IDNP0055159
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Sophocarpine
DescriptionSophocarpine 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. (-)-Sophocarpine is found in Ammodendron bifolium, Ammothamnus lehmanni Bge., Corydalis yanhusuo , Daphniphyllum oldhami, Leontice smirnovii, Sophora alopecuroides, Sophora davidii, Sophora flavescens , Sophora flavescens var. angustifolia , Sophora japonica L. , Sophora jaubertii, Sophora moorcroftiana Benth. , Sophora pachycarpa, Sophora subprostrata, Sophora tonkinensis, Sophora viciifolia, Styphnolobium japonicum and Vexibia pachycarpa. (-)-Sophocarpine was first documented in 2021 (PMID: 35002280). Based on a literature review a small amount of articles have been published on Sophocarpine (PMID: 35468537) (PMID: 35185568) (PMID: 35126158) (PMID: 34830730).
Structure
Thumb
Synonyms
ValueSource
13,14-Didehydro-matridin-15-oneMeSH
Sophocarpine hydrobromideMeSH
Chemical FormulaC15H22N2O
Average Mass246.3540 Da
Monoisotopic Mass246.17321 Da
IUPAC Name(1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one
Traditional Name(1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one
CAS Registry NumberNot Available
SMILES
O=C1C=CC[C@@H]2[C@H]3CCCN4CCC[C@@H](CN12)[C@@H]34
InChI Identifier
InChI=1S/C15H22N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15-/m0/s1
InChI KeyAAGFPTSOPGCENQ-JLNYLFASSA-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
Ammodendron bifoliumLOTUS Database
Ammothamnus lehmanni Bge.Plant
Corydalis yanhusuoPlant
Daphniphyllum oldhamiiPlant
Leontice smirnoviiPlant
Sophora alopecuroidesPlant
Sophora davidiiLOTUS Database
Sophora flavescensPlant
Sophora flavescens var. angustifoliaPlant
Sophora japonica L.Plant
Sophora jaubertiiLOTUS Database
Sophora moorcroftiana Benth.Plant
Sophora pachycarpaLOTUS Database
Sophora subprostrataPlant
Sophora tonkinensisLOTUS Database
Sophora viciifoliaPlant
Styphnolobium japonicumLOTUS Database
Vexibia pachycarpaPlant
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
  • Diazanaphthalene
  • Naphthyridine
  • Quinolizidine
  • Piperidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • 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
logP1.91ALOGPS
logP1.07ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)18.53ChemAxon
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.54 m³·mol⁻¹ChemAxon
Polarizability28.01 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 IDC00007759
Chemspider ID103136
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound115269
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Chen S, Ma S, Wang H, Shao X, Ding B, Guo Z, Chen X, Wang Y: Unraveling the mechanism of alkaloids from Sophora alopecuroides Linn combined with immune checkpoint blockade in the treatment of non-small cell lung cancer based on systems pharmacology. Bioorg Med Chem. 2022 Jun 15;64:116724. doi: 10.1016/j.bmc.2022.116724. Epub 2022 Mar 26. [PubMed:35468537 ]
  2. Zhang Z, Xie Z, Lv S, Shi Y, Zhai C, Li X, Qiao B, Gao X: Integrated Metabolomics and Network Pharmacology Study on the Mechanism of Kangfuxiaoyan Suppository for Treating Chronic Pelvic Inflammatory Disease. Front Pharmacol. 2022 Feb 4;13:812587. doi: 10.3389/fphar.2022.812587. eCollection 2022. [PubMed:35185568 ]
  3. Weng Q, Lan X, Wang Y, Fan C, Xu RA, Zhang P: Effect of Sophocarpine on the Pharmacokinetics of Umbralisib in Rat Plasma Using a Novel UPLC-MS/MS Method. Front Pharmacol. 2022 Jan 20;13:749095. doi: 10.3389/fphar.2022.749095. eCollection 2022. [PubMed:35126158 ]
  4. Wang DD, Wu XY, Dong JY, Cheng XP, Gu SF, Olatunji OJ, Li Y, Zuo J: Qing-Luo-Yin Alleviated Experimental Arthritis in Rats by Disrupting Immune Feedback Between Inflammatory T Cells and Monocytes: Key Evidences from Its Effects on Immune Cell Phenotypes. J Inflamm Res. 2021 Dec 30;14:7467-7486. doi: 10.2147/JIR.S346365. eCollection 2021. [PubMed:35002280 ]
  5. Yang G, Zeng R, Song X, Liu C, Ni L: Sophocarpine Alleviates Injury-Induced Intima Hyperplasia of Carotid Arteries by Suppressing Inflammation in a Rat Model. J Clin Med. 2021 Nov 22;10(22). pii: jcm10225449. doi: 10.3390/jcm10225449. [PubMed:34830730 ]