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Showing NP-Card for Shihunine (NP0051380)

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Record Information
Version2.0
Created at2022-04-27 22:46:09 UTC
Updated at2022-04-27 22:46:10 UTC
NP-MRD IDNP0051380
Secondary Accession NumbersNone
Natural Product Identification
Common NameShihunine
Description(1R)-1'-methyl-3H-spiro[2-benzofuran-1,2'-pyrrolidine]-3-one belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. Shihunine is found in Banisteriopsis caapi, Bessera tenuiflora, Dendrobium loddigesii, Dendrobium lohohense and Dendrobium pierardii. Based on a literature review very few articles have been published on (1R)-1'-methyl-3H-spiro[2-benzofuran-1,2'-pyrrolidine]-3-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051380 (Shihunine)


  Mrv1652304282200462D          

 15 17  0  0  1  0            999 V2000
    0.5638   -1.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573   -0.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679    0.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3810   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186   -0.7998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6915   -1.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -1.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -2.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -1.0803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0010   -0.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    0.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456    0.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
Download

3D MOL for NP0051380 (Shihunine)

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -1.6627   -1.2074   -1.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719   -0.7107    0.1239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.0125    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490    1.1842    1.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775    0.8595    1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4401    0.2690    0.2485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6014    1.2859   -0.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    1.4795   -1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407    2.3229   -2.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    0.5227   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613    0.3045   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133   -0.6623   -0.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -1.4068    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717   -1.1783    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179   -0.2166    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4519   -1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -2.1409   -1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7570   -1.4650   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2058    0.3803   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -0.6163    1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    2.0957    0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253    1.3598    2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    0.1034    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976    1.7580    1.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190    0.9086   -1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6474   -0.8438   -0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -2.1587    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -1.7878    1.5619 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  1  0
  6  7  1  6
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
  6  2  1  0
 15  6  1  0
 11 10  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
  5 23  1  0
  5 24  1  0
 14 28  1  0
 13 27  1  0
 12 26  1  0
 11 25  1  0
M  END
Download

3D SDF for NP0051380 (Shihunine)


  Mrv1652304282200462D          

 15 17  0  0  1  0            999 V2000
    0.5638   -1.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573   -0.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679    0.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3810   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186   -0.7998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6915   -1.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -1.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -2.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -1.0803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0010   -0.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    0.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456    0.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC[C@]11OC(=O)C2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO2/c1-13-8-4-7-12(13)10-6-3-2-5-9(10)11(14)15-12/h2-3,5-6H,4,7-8H2,1H3/t12-/m1/s1

> <INCHI_KEY>
YWAAZZCPWLHJAN-GFCCVEGCSA-N

> <FORMULA>
C12H13NO2

> <MOLECULAR_WEIGHT>
203.241

> <EXACT_MASS>
203.094628663

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.33810032301097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1'-methyl-3H-spiro[2-benzofuran-1,2'-pyrrolidine]-3-one

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
2.283875644666666

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.838872382717738

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
57.15360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1'-methylspiro[2-benzofuran-1,2'-pyrrolidine]-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0051380 (Shihunine)

Download
PDB for NP0051380 (Shihunine)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.052  -2.185   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.107  -0.969   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.687   0.457   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.212   0.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.158  -0.547   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.578  -1.974   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.341  -1.493   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.291  -3.032   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.189  -3.460   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.712  -4.908   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -2.790  -2.017   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -3.735  -0.801   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.871   0.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.392   0.046   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.217  -3.496   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8   11   14                                             
CONECT    8    7    9                                                       
CONECT    9    8    1   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

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3D PDB for NP0051380 (Shihunine)
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SMILES for NP0051380 (Shihunine)
CN1CCC[C@]11OC(=O)C2=C1C=CC=C2
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INCHI for NP0051380 (Shihunine)
InChI=1S/C12H13NO2/c1-13-8-4-7-12(13)10-6-3-2-5-9(10)11(14)15-12/h2-3,5-6H,4,7-8H2,1H3/t12-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H13NO2
Average Mass203.2410 Da
Monoisotopic Mass203.09463 Da
IUPAC Name(1R)-1'-methyl-3H-spiro[2-benzofuran-1,2'-pyrrolidine]-3-one
Traditional Name(1R)-1'-methylspiro[2-benzofuran-1,2'-pyrrolidine]-3-one
CAS Registry NumberNot Available
SMILES
CN1CCC[C@]11OC(=O)C2=C1C=CC=C2
InChI Identifier
InChI=1S/C12H13NO2/c1-13-8-4-7-12(13)10-6-3-2-5-9(10)11(14)15-12/h2-3,5-6H,4,7-8H2,1H3/t12-/m1/s1
InChI KeyYWAAZZCPWLHJAN-GFCCVEGCSA-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
Banisteriopsis caapiLOTUS Database
Bessera tenuifloraLOTUS Database
Dendrobium loddigesiiPlant
Dendrobium lohohensePlant
Dendrobium pierardiiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassBenzofuranones  
Direct ParentBenzofuranones  
Alternative Parents
Substituents
  • Benzofuranone
    • 

  • Phthalide
    • 

  • Isobenzofuranone
    • 

  • Isobenzofuran
    • 

  • Isocoumaran
    • 

  • N-alkylpyrrolidine
    • 

  • Benzenoid
    • 

  • Pyrrolidine
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP1.93ALOGPS
logP2.28ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity57.15 m³·mol⁻¹ChemAxon
Polarizability21.34 ųChemAxon
Number of Rings3ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92854553  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available