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Showing NP-Card for Stachydrine hydrochloride (NP0140485)

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Record Information
Version2.0
Created at2022-06-29 21:36:44 UTC
Updated at2022-06-29 21:36:45 UTC
NP-MRD IDNP0140485
Secondary Accession NumbersNone
Natural Product Identification
Common NameStachydrine hydrochloride
DescriptionStachydrine hydrochloride belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Stachydrine hydrochloride was first documented in 2020 (PMID: 32712088). Based on a literature review a small amount of articles have been published on Stachydrine hydrochloride (PMID: 35836883) (PMID: 35366490) (PMID: 33482468).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140485 (Stachydrine hydrochloride)


  Mrv1652306292223362D          

 11 10  0  0  1  0            999 V2000
   -0.0380    0.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.2718    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1815   -0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266   -0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016   -0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534   -0.2131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9380    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511   -0.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.8488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0661    0.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5387    0.0000    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
M  CHG  2   2   1  11  -1
M  END
Download

3D MOL for NP0140485 (Stachydrine hydrochloride)

     RDKit          3D

 25 24  0  0  0  0  0  0  0  0999 V2000
   -1.1103   -1.2773    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6463   -0.3617   -0.0634 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3105   -0.7045   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0494    0.9895    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034    1.8942   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0878    1.0664   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7589   -0.3373   -0.3024 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6059   -0.7016    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1365   -1.0057    1.9607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9785   -0.7080    0.6818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0 15  0  0  0  0  0  0
   -2.1644   -1.5721    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.8559    1.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5529   -2.2342    0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -0.1906   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3957   -1.8078   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6878   -0.4054   -2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278    1.3022   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988    1.0480    1.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2202    2.8085   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6198    2.1815    0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304    1.0870   -1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    1.3354   -0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0092   -1.0430   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -0.5077    1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  7  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
 10 25  1  0
M  CHG  2   2   1  11  -1
M  END
Download

3D SDF for NP0140485 (Stachydrine hydrochloride)


  Mrv1652306292223362D          

 11 10  0  0  1  0            999 V2000
   -0.0380    0.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.2718    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1815   -0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266   -0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016   -0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534   -0.2131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9380    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511   -0.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.8488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0661    0.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5387    0.0000    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
M  CHG  2   2   1  11  -1
M  END
> <DATABASE_ID>
NP0140485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Cl-].C[N+]1(C)CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO2.ClH/c1-8(2)5-3-4-6(8)7(9)10;/h6H,3-5H2,1-2H3;1H/t6-;/m0./s1

> <INCHI_KEY>
DUNMULOWUUIQIL-RGMNGODLSA-N

> <FORMULA>
C7H14ClNO2

> <MOLECULAR_WEIGHT>
179.64

> <EXACT_MASS>
179.0713064

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
15.475108404283171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-carboxy-1,1-dimethylpyrrolidin-1-ium chloride

> <ALOGPS_LOGP>
-2.97

> <JCHEM_LOGP>
-3.8764300881384117

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.258526077274334

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
49.272600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1-dimethyl-prolinium chloride

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0140485 (Stachydrine hydrochloride)

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PDB for NP0140485 (Stachydrine hydrochloride)
HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -0.071   1.652   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.960   0.507   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       2.206  -0.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.730  -1.863   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.190  -1.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.286  -0.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.751   0.078   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.895  -0.952   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.071   1.584   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.990   1.652   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       6.606   0.000   0.000  0.00  0.00          Cl-1
CONECT    1    2                                                            
CONECT    2    1    3    6   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0140485 (Stachydrine hydrochloride)
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SMILES for NP0140485 (Stachydrine hydrochloride)
[Cl-].C[N+]1(C)CCC[C@H]1C(O)=O
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INCHI for NP0140485 (Stachydrine hydrochloride)
InChI=1S/C7H13NO2.ClH/c1-8(2)5-3-4-6(8)7(9)10;/h6H,3-5H2,1-2H3;1H/t6-;/m0./s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H14ClNO2
Average Mass179.6400 Da
Monoisotopic Mass179.07131 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
[Cl-].C[N+]1(C)CCC[C@H]1C(O)=O
InChI Identifier
InChI=1S/C7H13NO2.ClH/c1-8(2)5-3-4-6(8)7(9)10;/h6H,3-5H2,1-2H3;1H/t6-;/m0./s1
InChI KeyDUNMULOWUUIQIL-RGMNGODLSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentProline and derivatives  
Alternative Parents
Substituents
  • Proline or derivatives
    • 

  • Alpha-amino acid
    • 

  • L-alpha-amino acid
    • 

  • Pyrrolidine carboxylic acid
    • 

  • Pyrrolidine carboxylic acid or derivatives
    • 

  • N-alkylpyrrolidine
    • 

  • Tetraalkylammonium salt
    • 

  • Pyrrolidine
    • 

  • Quaternary ammonium salt
    • 

  • Carboxylic acid salt
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic salt
    • 

  • Hydrochloride
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic cation
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16498851  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17751044  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li XQ, Lu S, Xia L, Shan XL, Zhao WX, Chen HH, Zhang C, Guo W, Xu M, Lu R, Zhao P: Stachydrine hydrochloride ameliorates cardiac hypertrophy through CaMKII/HDAC4/MEF2C signal pathway. Am J Transl Res. 2022 Jun 15;14(6):3840-3853. eCollection 2022. [PubMed:35836883  ] 
  2. Bao X, Liu Y, Huang J, Yin S, Sheng H, Han X, Chen Q, Wang T, Chen S, Qiu Y, Zhang C, Yu H: Stachydrine hydrochloride inhibits hepatocellular carcinoma progression via LIF/AMPK axis. Phytomedicine. 2022 Jun;100:154066. doi: 10.1016/j.phymed.2022.154066. Epub 2022  Mar 21. [PubMed:35366490  ] 
  3. Chen M, Yang D, Hu X, Jiang G, Li T, Ouyang Z, Deng J: Stachydrine hydrochloride inhibits osteoclastogenesis by regulating the NF-kappaB and p38 signaling pathways to alleviate postmenopausal osteoporosis. Biochem Biophys Res Commun. 2021 Jan 19;542:1-8. doi: 10.1016/j.bbrc.2021.01.012. [PubMed:33482468  ] 
  4. Zheng J, Tian J, Wang S, Hu P, Wu Q, Shan X, Zhao P, Zhang C, Guo W, Xu M, Chen H, Lu R: Stachydrine hydrochloride suppresses phenylephrine-induced pathological cardiac hypertrophy by inhibiting the calcineurin/nuclear factor of activated T-cell signalling pathway. Eur J Pharmacol. 2020 Sep 15;883:173386. doi: 10.1016/j.ejphar.2020.173386. Epub  2020 Jul 24. [PubMed:32712088  ]