NP-MRD: Showing NP-Card for (+)-Isoboldine (NP0050988)

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Record Information

Version

2.0

Created at

2022-04-27 22:26:52 UTC

Updated at

2022-04-27 22:26:52 UTC

NP-MRD ID

NP0050988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Isoboldine

Description

(+)-Isoboldine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof (+)-Isoboldine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (+)-Isoboldine is found in Aconitum karacolicum, Aconitum karakolicum, Aconitum sanyoense, Aconitum saposhnikovii, Aniba canelilla , Annickia polycarpa, Annona cherimola, Annona cherimolia, Annona senegalensis , Anomianthus dulcis , Anonna salzmanii, Beilschmiedia alloiophylla, Berberis brandisiana, Berberis cretica, Berberis integerrima, Berberis nummularia, Cardiopetalum calophyllum, Cassytha filiformis , Ceratocapnos palaestinus, Cocculus laurifolius, Cocculus trilobus, Corydalis bulleyana, Corydalis bungeana , Corydalis caucasia, Corydalis cava , Corydalis gortschakovii, Corydalis intermedia, Corydalis nobilis, Corydalis solida , Croton celtidifolius, Croton lechleri, Croton lechleri Mull.Arg. , Cryptocarya chinensis, Dehaasia incrassata, Dehaasia triandra, Dicentra peregrina, Erythrina abyssinica , Erythrina poeppigiana , Fissistigma oldhamii, Fumaria agraria, Fumaria bella, Fumaria capreolata , Fumaria parviflora, Fumaria vaillantii, Glaucium arabicum, Glaucium fimbrilligerum, Glaucium flavum , Glaucium grandiflorum, Glossocalyx brevipes, Greenwayodendron oliveri, Guatteria goudotiana, Guatteria megalophylla, Houttuynia cordata , Lindera aggregata, Lindera angustifolia, Lindera glauca, Lindera sericea, Litsea acuminata, Litsea cubeba , Litsea glutinosa , Litsea sericea, Litsea wightiana, Monodora junodii, Nandina domestica , Nectandra grandiflora, Nectandra membranacea, Nectandra salicifolia, Neolitsea konishii, Ocotea caesia, Ocotea glaziovii, Ocotea lancifolia, Pachygone dasycarpa, Pachygone ovata, Papaver bracteatum, Papaver orientale , Papaver pinnatifidum, Papaver rhoeas , Papaver setigerum, Papaver somniferum, Peumus boldus , Phoebe minutiflora, Thuja orientalis , Sarcocapnos crassifolia, Sassafras albidum, Schefferomitra subaequalis, Stephania cepharantha , Stephania excentrica, Stephania officinarum, Stylophorum diphyllum, Stylophorum lasiocarpum, Thalictrum alpinum, Thalictrum aquilegiifolium, Thalictrum collinum, Thalictrum foetidum , Thalictrum isopyroides, Uvaria dulcis, Xylopia danguyella, Xylopia parviflora and Xylopia vieillardi. (+)-Isoboldine was first documented in 2015 (PMID: 26108161). Based on a literature review a small amount of articles have been published on (+)-Isoboldine (PMID: 34179304) (PMID: 32359855) (PMID: 30989951) (PMID: 26055342).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    5.0063    1.6035   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152    0.2108   -0.3163 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6975   -0.4309   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5383    0.3424   -0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.2928   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2192   -1.6640   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4021   -2.4024   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278   -1.8248   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -2.5686   -0.5318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860   -2.3556   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0945   -1.6837    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1096   -0.2156    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896    0.4913    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637    1.8597    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    2.5417    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    3.9196   -0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213    4.7666    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    1.8450   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    2.5624   -0.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1010    0.4764   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133   -0.1652    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761   -1.4793    1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -2.1809    0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066   -3.5590    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0722    1.8909   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710    2.0021    0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612    2.0621   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7155    1.3857   -0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -3.4767   -0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713   -2.0908   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134   -3.4246   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520   -2.3969   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -1.8571    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839    2.4552    0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865    4.9123    1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631    5.7725   -0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694    4.3892   -0.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3213    3.5704   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619   -0.4294   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    0.4757    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2886   -2.0320    1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8862   -1.2099    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259   -4.0594    1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6015   -3.7583   -0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8506   -3.9776   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 10  1  0
 10 11  1  0
 11 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 13  1  0
 13 12  1  0
 12 20  2  0
 20 18  1  0
 18 19  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 20  5  1  0
 12 11  1  0
 14 13  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 24 43  1  0
 24 44  1  0
 24 45  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 19 38  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 14 34  1  0
  7 29  1  0
  9 30  1  0
M  END


  Mrv1652304282200262D          

 24 27  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H]3N(C)CCC4=C3C2=C(O)C(OC)=C4)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO4/c1-20-5-4-10-8-16(24-3)19(22)18-12-9-15(23-2)14(21)7-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1

> <INCHI_KEY>
LINHZVMHXABQLB-ZDUSSCGKSA-N

> <FORMULA>
C19H21NO4

> <MOLECULAR_WEIGHT>
327.38

> <EXACT_MASS>
327.14705816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.78692338472359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,16-diol

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.7789388529999997

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.21362783701868

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.507123347689935

> <JCHEM_PKA_STRONGEST_BASIC>
6.777286894610318

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
92.91449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,16-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21                                                            
CONECT   23   11                                                            
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
Isoboldine	Kegg
2,10-Dimethoxy-6aalpha-aporphine-1,9-diol	Kegg

Chemical Formula

C₁₉H₂₁NO₄

Average Mass

327.3800 Da

Monoisotopic Mass

327.14706 Da

IUPAC Name

(9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,16-diol

Traditional Name

(9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,16-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C[C@@H]3N(C)CCC4=C3C2=C(O)C(OC)=C4)C=C1O

InChI Identifier

InChI=1S/C19H21NO4/c1-20-5-4-10-8-16(24-3)19(22)18-12-9-15(23-2)14(21)7-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1

InChI Key

LINHZVMHXABQLB-ZDUSSCGKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum karacolicum	Plant	KNApSAcK
Aconitum karakolicum	LOTUS Database	35616633
Aconitum sanyoense	LOTUS Database	35616633
Aconitum saposhnikovii	Plant	KNApSAcK
Aniba canelilla	Plant	KNApSAcK
Annickia polycarpa	LOTUS Database	35616633
Annona cherimola	LOTUS Database	35616633
Annona cherimolia	Plant	KNApSAcK
Annona senegalensis	Plant	KNApSAcK
Anomianthus dulcis	Plant	KNApSAcK
Anonna salzmanii	Plant	KNApSAcK
Beilschmiedia alloiophylla	LOTUS Database	35616633
Berberis brandisiana	Plant	KNApSAcK
Berberis cretica	LOTUS Database	35616633
Berberis integerrima	LOTUS Database	35616633
Berberis nummularia	LOTUS Database	35616633
Cardiopetalum calophyllum	Plant	KNApSAcK
Cassytha filiformis	Plant	KNApSAcK
Ceratocapnos palaestinus	Plant	KNApSAcK
Cocculus laurifolius	Plant	KNApSAcK
Cocculus trilobus	LOTUS Database	35616633
Corydalis bulleyana	LOTUS Database	35616633
Corydalis bungeana	Plant	KNApSAcK
Corydalis caucasia	Plant	KNApSAcK
Corydalis cava	Plant	KNApSAcK
Corydalis gortschakovii	Plant	KNApSAcK
Corydalis intermedia	Plant	KNApSAcK
Corydalis nobilis	Plant	KNApSAcK
Corydalis solida	Plant	KNApSAcK
Croton celtidifolius	Plant	KNApSAcK
Croton lechleri	LOTUS Database	35616633
Croton lechleri Mull.Arg.	Plant	KNApSAcK
Cryptocarya chinensis	Plant	KNApSAcK
Dehaasia incrassata	LOTUS Database	35616633
Dehaasia triandra	Plant	KNApSAcK
Dicentra peregrina	LOTUS Database	35616633
Erythrina abyssinica	Plant	KNApSAcK
Erythrina poeppigiana	Plant	KNApSAcK
Fissistigma oldhamii	LOTUS Database	35616633
Fumaria agraria	Plant	KNApSAcK
Fumaria bella	Plant	KNApSAcK
Fumaria capreolata	Plant	KNApSAcK
Fumaria parviflora	LOTUS Database	35616633
Fumaria vaillantii	LOTUS Database	35616633
Glaucium arabicum	Plant	KNApSAcK
Glaucium fimbrilligerum	LOTUS Database	35616633
Glaucium flavum	Plant	KNApSAcK
Glaucium grandiflorum	Plant	KNApSAcK
Glossocalyx brevipes	LOTUS Database	35616633
Greenwayodendron oliveri	LOTUS Database	35616633
Guatteria goudotiana	Plant	KNApSAcK
Guatteria megalophylla	LOTUS Database	35616633
Houttuynia cordata	Plant	KNApSAcK
Lindera aggregata	LOTUS Database	35616633
Lindera angustifolia	LOTUS Database	35616633
Lindera glauca	Plant	KNApSAcK
Lindera sericea	LOTUS Database	35616633
Litsea acuminata	Plant	KNApSAcK
Litsea cubeba	Plant	KNApSAcK
Litsea glutinosa	Plant	KNApSAcK
Litsea sericea	LOTUS Database	35616633
Litsea wightiana	LOTUS Database	35616633
Monodora junodii	LOTUS Database	35616633
Nandina domestica	Plant	KNApSAcK
Nectandra grandiflora	Plant	KNApSAcK
Nectandra membranacea	Plant	KNApSAcK
Nectandra salicifolia	Plant	KNApSAcK
Neolitsea konishii	Plant	KNApSAcK
Ocotea caesia	Plant	KNApSAcK
Ocotea glaziovii	LOTUS Database	35616633
Ocotea lancifolia	LOTUS Database	35616633
Pachygone dasycarpa	Plant	KNApSAcK
Pachygone ovata	LOTUS Database	35616633
Papaver bracteatum	LOTUS Database	35616633
Papaver orientale	Plant	KNApSAcK
Papaver pinnatifidum	Plant	KNApSAcK
Papaver rhoeas	Plant	KNApSAcK
Papaver setigerum	Plant	KNApSAcK
Papaver somniferum	LOTUS Database	35616633
Peumus boldus	Plant	KNApSAcK
Phoebe minutiflora	Plant	KNApSAcK
Platycladus orientalis	Plant	KNApSAcK
Sarcocapnos crassifolia	LOTUS Database	35616633
Sassafras albidum	LOTUS Database	35616633
Schefferomitra subaequalis	LOTUS Database	35616633
Stephania cephalantha	Plant	KNApSAcK
Stephania excentrica	Plant	KNApSAcK
Stephania officinarum	Plant	KNApSAcK
Stylophorum diphyllum	LOTUS Database	35616633
Stylophorum lasiocarpum	Plant	KNApSAcK
Thalictrum alpinum	LOTUS Database	35616633
Thalictrum aquilegifolium	LOTUS Database	35616633
Thalictrum collinum	Plant	KNApSAcK
Thalictrum foetidum	Plant	KNApSAcK
Thalictrum isopyroides	LOTUS Database	35616633
Uvaria dulcis	LOTUS Database	35616633
Xylopia danguyella	Plant	KNApSAcK
Xylopia parviflora	Plant	KNApSAcK
Xylopia vieillardi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
1-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:5986 )
Isoquinoline alkaloids (C09541 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.34	ALOGPS
logP	2.78	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	6.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	35.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001869

Chemspider ID

117620

KEGG Compound ID

C09541

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133323

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chaturvedi M, Nagre K, Yadav JP: In silico approach for identification of natural compounds as potential COVID 19 main protease (M(pro)) inhibitors. Virusdisease. 2021 Jun;32(2):325-329. doi: 10.1007/s13337-021-00701-7. Epub 2021 Jun 20. [PubMed:34179304 ]
Kuo PC, Wu YH, Hung HY, Lam SH, Ma GH, Kuo LM, Hwang TL, Kuo DH, Wu TS: Anti-inflammatory principles from Lindera aggregata. Bioorg Med Chem Lett. 2020 Jul 1;30(13):127224. doi: 10.1016/j.bmcl.2020.127224. Epub 2020 Apr 27. [PubMed:32359855 ]
Yang XL, Yang YP, Ge YW, Meng J: [Chemical constituents in chloroform fraction of Houttuynia cordata]. Zhongguo Zhong Yao Za Zhi. 2019 Jan;44(2):314-318. doi: 10.19540/j.cnki.cjcmm.2019.0007. [PubMed:30989951 ]
Soares ER, da Silva FM, de Almeida RA, de Lima BR, da Silva Filho FA, Barison A, Koolen HH, Pinheiro ML, de Souza AD: Direct infusion ESI-IT-MSn alkaloid profile and isolation of tetrahydroharman and other alkaloids from Bocageopsis pleiosperma maas (Annonaceae). Phytochem Anal. 2015 Sep-Oct;26(5):339-45. doi: 10.1002/pca.2568. Epub 2015 Jun 24. [PubMed:26108161 ]
Li Y, Zeng RJ, Chen JZ, Wu YB, Chou GX, Gao Y, Shao JW, Cai HZ, Jia L: Pharmacokinetics and metabolism study of isoboldine, a major bioactive component from Radix Linderae in male rats by UPLC-MS/MS. J Ethnopharmacol. 2015 Aug 2;171:154-60. doi: 10.1016/j.jep.2015.05.042. Epub 2015 Jun 6. [PubMed:26055342 ]

Showing NP-Card for (+)-Isoboldine (NP0050988)

MOL for NP0050988 ((+)-Isoboldine)

3D MOL for NP0050988 ((+)-Isoboldine)

3D SDF for NP0050988 ((+)-Isoboldine)

3D-SDF for NP0050988 ((+)-Isoboldine)

PDB for NP0050988 ((+)-Isoboldine)

3D PDB for NP0050988 ((+)-Isoboldine)

SMILES for NP0050988 ((+)-Isoboldine)

INCHI for NP0050988 ((+)-Isoboldine)

Structure for NP0050988 ((+)-Isoboldine)

3D Structure for NP0050988 ((+)-Isoboldine)