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Showing NP-Card for hydrastinine (NP0289436)

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Record Information
Version2.0
Created at2022-09-09 19:37:21 UTC
Updated at2022-09-09 19:37:21 UTC
NP-MRD IDNP0289436
Secondary Accession NumbersNone
Natural Product Identification
Common Namehydrastinine
Description6-Methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. hydrastinine is found in Chelidonium majus, Dactylicapnos torulosa and Hydrastis canadensis. 6-Methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0289436 (hydrastinine)


  Mrv1652306031608552D          

 15 17  0  0  0  0            999 V2000
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
Download

3D MOL for NP0289436 (hydrastinine)

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.2288    1.2459    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761    0.4341    0.5456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663   -0.9476    0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781   -1.6935    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520   -0.9582    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -1.3451    0.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388   -0.6934   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    0.3786   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987    0.7741   -1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0457    0.1155   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311    0.5468   -0.7688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5337    1.8275   -1.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687    0.8210   -1.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5945    0.2404   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -0.8952   -0.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1454    0.8350    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815    2.2691    0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574    1.3631    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650   -1.4129    0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -0.9962    1.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391   -1.7822    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -2.7442    0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -2.2001    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807    1.6274   -1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446   -0.1381   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148    2.4160   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.9598    0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753   -0.0474   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
 10  5  1  0
 15  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
 14 27  1  0
 14 28  1  0
  9 24  1  0
 11 25  1  6
 12 26  1  0
M  END
Download

3D SDF for NP0289436 (hydrastinine)


  Mrv1652306031608552D          

 15 17  0  0  0  0            999 V2000
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289436

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=CC3=C(OCO3)C=C2C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3

> <INCHI_KEY>
YOJQZPVUNUQTDF-UHFFFAOYSA-N

> <FORMULA>
C11H13NO3

> <MOLECULAR_WEIGHT>
207.229

> <EXACT_MASS>
207.089543283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.55107707142116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
1.213540615333334

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.788272886238545

> <JCHEM_PKA_STRONGEST_BASIC>
6.092611733288772

> <JCHEM_POLAR_SURFACE_AREA>
41.93000000000001

> <JCHEM_REFRACTIVITY>
54.70710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydrastinine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0289436 (hydrastinine)

Download
PDB for NP0289436 (hydrastinine)
HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.531   3.613   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       5.198   5.923   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    7                                                       
CONECT    3    2   12                                                       
CONECT    4    7    9                                                       
CONECT    5    8   10                                                       
CONECT    6   14   15                                                       
CONECT    7    2    4    8                                                  
CONECT    8    5    7   11                                                  
CONECT    9    4   10   14                                                  
CONECT   10    5    9   15                                                  
CONECT   11    8   12   13                                                  
CONECT   12    1    3   11                                                  
CONECT   13   11                                                            
CONECT   14    6    9                                                       
CONECT   15    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

Download
3D PDB for NP0289436 (hydrastinine)
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SMILES for NP0289436 (hydrastinine)
CN1CCC2=CC3=C(OCO3)C=C2C1O
Download
INCHI for NP0289436 (hydrastinine)
InChI=1S/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3
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View in JSmol
Synonyms
ValueSource
Hydrastinine hydrochlorideMeSH
Hydrastinine chlorideMeSH
Hydrastinine hydroxideMeSH
Chemical FormulaC11H13NO3
Average Mass207.2290 Da
Monoisotopic Mass207.08954 Da
IUPAC Name6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol
Traditional Namehydrastinine
CAS Registry NumberNot Available
SMILES
CN1CCC2=CC3=C(OCO3)C=C2C1O
InChI Identifier
InChI=1S/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3
InChI KeyYOJQZPVUNUQTDF-UHFFFAOYSA-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
Chelidonium majusLOTUS Database
Dactylicapnos torulosaLOTUS Database
Hydrastis canadensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassTetrahydroisoquinolines  
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines  
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
    • 

  • Benzodioxole
    • 

  • Benzenoid
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Alkanolamine
    • 

  • Acetal
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP0.62ALOGPS
logP1.21ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)12.79ChemAxon
pKa (Strongest Basic)6.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.71 m³·mol⁻¹ChemAxon
Polarizability21.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3638  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]