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Showing NP-Card for Gelsemide (NP0057472)

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Record Information
Version2.0
Created at2022-04-28 02:53:49 UTC
Updated at2022-04-28 02:53:49 UTC
NP-MRD IDNP0057472
Secondary Accession NumbersNone
Natural Product Identification
Common NameGelsemide
DescriptionGelsemide belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Gelsemide is found in Gelsemium elegans and Gelsemium sempervirens . Gelsemide was first documented in 2008 (PMID: 18520100). Based on a literature review very few articles have been published on Gelsemide.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057472 (Gelsemide)


  Mrv1652304282204532D          

 15 17  0  0  1  0            999 V2000
    2.0025   -0.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1559    0.2553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9345    0.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -0.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -1.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -2.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.7867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975   -0.9838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6721   -0.4457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9907    0.3153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5514    1.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308   -0.6353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0386    1.0719    0.0000 O   0  0  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  2  0  0  0  0
  1  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 11 14  1  1  0  0  0
  2 15  1  6  0  0  0
M  END
Download

3D MOL for NP0057472 (Gelsemide)

     RDKit          3D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.1266   -1.3974    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486   -0.5835   -0.2758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3272    0.8759   -0.0346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4295    1.5700   -1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1805    1.4476    0.7354 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3580    2.6233    0.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5232    2.3484   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    3.1509   -1.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7026    0.9007   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646    0.0280   -1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938   -1.3118   -0.8896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699   -1.8383   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648   -0.9053    0.4007 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0345   -1.5307    1.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128    0.4113    0.6828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1384   -0.9762    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.2579    1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -2.4693    0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -0.8457   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    1.0229    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842    2.0664   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4517    1.7096    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242    0.4029   -2.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -2.1671   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3048   -2.7922    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870   -0.9160    2.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    0.4335    1.5567 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 13  2  1  0
 15  5  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  1
  4 21  1  0
  5 22  1  1
 10 23  1  0
 12 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  1
M  END
Download

3D SDF for NP0057472 (Gelsemide)


  Mrv1652304282204532D          

 15 17  0  0  1  0            999 V2000
    2.0025   -0.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1559    0.2553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9345    0.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -0.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -1.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -2.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.7867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975   -0.9838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6721   -0.4457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9907    0.3153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5514    1.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308   -0.6353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0386    1.0719    0.0000 O   0  0  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  2  0  0  0  0
  1  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 11 14  1  1  0  0  0
  2 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0057472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](O)[C@@H]2OC(=O)C3=COC[C@@]1(O)[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-4-7(11)8-6-5(9(12)15-8)2-14-3-10(4,6)13/h2,4,6-8,11,13H,3H2,1H3/t4-,6-,7-,8+,10-/m0/s1

> <INCHI_KEY>
CLHRRLZEKMQHFZ-HZHVFOLNSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.201

> <EXACT_MASS>
212.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.556800933337875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5S,6S,7S,11S)-5,7-dihydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.0^{4,11}]undec-1(10)-en-2-one

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-1.064340533333333

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.041787277304927

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.199697735359791

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3157549124900765

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
48.2527

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5S,6S,7S,11S)-5,7-dihydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.0^{4,11}]undec-1(10)-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0057472 (Gelsemide)

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PDB for NP0057472 (Gelsemide)
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       3.738  -1.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.024   0.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.478   0.985   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.645  -0.019   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.359  -1.532   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.905  -2.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.311  -3.462   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.110  -4.778   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.776  -3.335   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.422  -1.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.255  -0.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.849   0.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.029   1.892   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.244  -1.186   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.805   2.001   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3   12   15                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

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3D PDB for NP0057472 (Gelsemide)
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SMILES for NP0057472 (Gelsemide)
C[C@H]1[C@H](O)[C@@H]2OC(=O)C3=COC[C@@]1(O)[C@H]23
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INCHI for NP0057472 (Gelsemide)
InChI=1S/C10H12O5/c1-4-7(11)8-6-5(9(12)15-8)2-14-3-10(4,6)13/h2,4,6-8,11,13H,3H2,1H3/t4-,6-,7-,8+,10-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H12O5
Average Mass212.2010 Da
Monoisotopic Mass212.06847 Da
IUPAC Name(4R,5S,6S,7S,11S)-5,7-dihydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.0^{4,11}]undec-1(10)-en-2-one
Traditional Name(4R,5S,6S,7S,11S)-5,7-dihydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.0^{4,11}]undec-1(10)-en-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H](O)[C@@H]2OC(=O)C3=COC[C@@]1(O)[C@H]23
InChI Identifier
InChI=1S/C10H12O5/c1-4-7(11)8-6-5(9(12)15-8)2-14-3-10(4,6)13/h2,4,6-8,11,13H,3H2,1H3/t4-,6-,7-,8+,10-/m0/s1
InChI KeyCLHRRLZEKMQHFZ-HZHVFOLNSA-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
Gelsemium elegansLOTUS Database
Gelsemium sempervirensPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassFuropyrans  
Sub ClassNot Available
Direct ParentFuropyrans  
Alternative Parents
Substituents
  • Furopyran
    • 

  • Gamma butyrolactone
    • 

  • Pyran
    • 

  • Cyclic alcohol
    • 

  • Furan
    • 

  • Tertiary alcohol
    • 

  • Tetrahydrofuran
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Vinylogous ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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
logP-0.79ALOGPS
logP-1.1ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.25 m³·mol⁻¹ChemAxon
Polarizability19.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00010557  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101415981  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kogure N, Ishii N, Kobayashi H, Kitajima M, Wongseripipatana S, Takayama H: New iridoids from Gelsemium species. Chem Pharm Bull (Tokyo). 2008 Jun;56(6):870-2. doi: 10.1248/cpb.56.870. [PubMed:18520100  ]