NP-MRD: Showing NP-Card for (+)-Magnoflorine (NP0051001)

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Record Information

Version

2.0

Created at

2022-04-27 22:27:22 UTC

Updated at

2022-04-27 22:27:22 UTC

NP-MRD ID

NP0051001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Magnoflorine

Description

(S)-magnoflorine 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 (S)-magnoflorine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (+)-Magnoflorine is found in Aconitum callibotryon, Aconitum lycoctonum, Aconitum vulparia, Actaea racemosa , Actaea spicata , Anamirta cocculus, Apis cerana, Aquilegia alpina, Aquilegia coerulea, Aquilegia olympica, Argemone platyceras Link et Otto, Argemone polyanthemos, Argemone spp., Aristolochia bracteolata, Aristolochia clematitis , Aristolochia contorta , Aristolochia cymbifera, Aristolochia debilis , Aristolochia elegans , Aristolochia fangchi, Aristolochia gigantea, Aristolochia heterophylla , Aristolochia indica, Aristolochia manshuriensis, Aristolochia moupinensis, Aristolochia sipho, Aristolochia thunbergii, Aristolochia triangularis, Asteropyrum cavaleriei, Berberis actinacantha, Berberis amurensis , Berberis aquifolium, Berberis crataegina , Berberis cretica, Berberis darwinii, Berberis heteropoda, Berberis iliensis, Berberis integerrima, Berberis kawakamii, Berberis nummularia, Berberis numularis, Berberis thunbergii , Berberis vulgaris , Caltha palustris , Caulophyllum thalicroides, Caulophyllum thalictroides , Chelidonium spp., Cissampelos pareira , Clematis parviloba, Cocculus carolinus, Cocculus hirsutus, Cocculus trilobus , Consolida regalis, Coptis chinensis , Coptis deltoidea , Coptis japonica , Coptis quinquefolia, Coptis teetoides, Corydalis bungeana , Corydalis intermedia, Corydalis spp., Croton cumingii, Croton lechleri, Croton lechleri Mull.Arg. , Croton menthodorus, Cymbopetalum brasiliense, Delphinium fangshanense W.T., Delphinium pentagynum, Dicranostigma spp., Dilphinium caeruleum, Dioscoreophyllum cumminsii, Diploclisia glaucescens , Epimedium brevicornum , Eschscholzia californica , Eschscholzia spp., Fumaria capreolata, Glaucium arabicum, Glaucium fimbrilligerum, Glaucium flavum , Glaucium spp., Glaucium squamigerum, Hernandia nymphaeifolia, Hypecoum procumbens, Hypserpa nitida, Isopyrum thalictroides, Litsea deccanensis, Magnolia accuminata, Magnolia denudata , Magnolia grandiflora , Magnolia kobus , Magnolia officinalis , Magnolia soulangeana, Magnolia speciosa, Mahonia fortunei, Mahonia japonica, Meconopsis cambrica, Meconopsis robusta, Meconopsis spp., Menispermum canadense, Monodora junodii, Monodora tenuifolia, Nandina domestica, Pachygone ovata, Papaver bracteatum, Papaver glaucum, Papaver orientale , Papaver pavoninum, Papaver rhoeas , Papaver setigerum, Papaver somniferum , Papaver spp., Paraquilegia anemonoides, Phellodendron amurense , Phellodendron chinense , Phellodendron chinense var.glabriusculum , Podophyllum peltatum , Potentilla discolor, Ranunculus serbicus, Rhigiocarya racemifera, Semiaquilegia adoxoides, Sinomenium acutum , Stephania cepharantha , Stephania elegans, Stephania pierrei, Stylophorum diphyllum, Stylophorum lasiocarpum, Thalictrum aquilegiifolium, Thalictrum baicalense, Thalictrum cultratum, Thalictrum dasycarpum, Thalictrum delavayi, Thalictrum flavum L., Thalictrum foetidum , Thalictrum foliolosum , Thalictrum foliosum, Thalictrum isopyroides, Thalictrum javanicum, Thalictrum longipedunculatum, Thalictrum lucidum, Thalictrum minums, Thalictrum minus, Thalictrum thunbergii, Thalictrum petaloideum, Thalictrum podocarpum, Thalictrum przewalskii, Thalictrum simplex, Thalictrum symplex, Thalictrum thalictroides, Thalictrum urbainii, Thalictrum wangii, Tinospora capillipes, Tinospora cordifolia , Tinospora crispa , Tinospora malabrica, Toddalia asiatica, Xylopia parviflora , Xylopia vieillardi, Zanthoxylum austrosinense, Zanthoxylum chalybeum , Zanthoxylum gilletii, Zanthoxylum mayu, Zanthoxylum myriacanthum, Zanthoxylum nitidum , Zanthoxylum piperitum, Zanthoxylum rhoifolium, Zanthoxylum scandens, Zanthoxylum spp., Zanthoxylum usambarense, Zanthoxylum usambarensis, Ziziphus jujuba and Zizyphus jujuba var. spinosa . (+)-Magnoflorine was first documented in 2020 (PMID: 33258352). Based on a literature review a small amount of articles have been published on (S)-magnoflorine (PMID: 34802347) (PMID: 34415741) (PMID: 34194523).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200272D          

 25 28  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  3  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   -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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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
 11 12  1  0  0  0  0
 12  3  1  1  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
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 11 23  1  0  0  0  0
 11 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  CHG  1  11   1
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    5.3792   -3.0270   -1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312   -1.8014   -0.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3546   -1.7857   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6444   -2.9420   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747   -2.9060   -0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234   -1.7187   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3552   -0.5551   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -0.5683   -0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    0.4816   -0.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6272    0.6443   -0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    1.8513   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861    2.0489   -0.2084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839    3.0067    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0946    4.2511    0.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    5.4515    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561    2.9037    0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981    1.6794    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558    0.5499    0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.7981    0.3081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8673   -1.7507   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7996   -0.7996    0.4654 N   0  0  2  0  0  4  0  0  0  0  0  0
   -3.1734   -2.0229    1.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287   -0.7775   -0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2639    0.3029    1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653    1.5955    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194   -3.3940   -2.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4668   -2.8631   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -3.7475   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1496   -3.8730   -1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031   -3.8095   -1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5513    0.4252   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.9931   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918    5.7025   -0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    5.3989    1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584    6.2563    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    3.7765    0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9768   -1.1596    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126   -2.7862   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -1.3859   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -2.9297    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5936   -1.9909    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475   -1.9997    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241   -1.8472   -1.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5678   -0.3899   -0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784   -0.1555   -1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379    0.1461    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653    0.3334    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    2.4198    1.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218    1.5661   -0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 19 21  1  0
 21 22  1  1
 21 23  1  0
 21 24  1  0
 24 25  1  0
 11 13  1  0
 25 17  1  0
 10 18  1  0
  5  6  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  1
 20 38  1  0
 20 39  1  0
  9 31  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 12 32  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
M  CHG  1  21   1
M  END


  Mrv1652304282200272D          

 25 28  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  3  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   -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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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
 11 12  1  0  0  0  0
 12  3  1  1  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
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 11 23  1  0  0  0  0
 11 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  CHG  1  11   1
M  END
> <DATABASE_ID>
NP0051001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=C(C(O)=C(OC)C=C4)C3=C1O)[N+](C)(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-21(2)8-7-12-10-15(25-4)20(23)18-16(12)13(21)9-11-5-6-14(24-3)19(22)17(11)18/h5-6,10,13H,7-9H2,1-4H3,(H-,22,23)/p+1/t13-/m0/s1

> <INCHI_KEY>
YLRXAIKMLINXQY-ZDUSSCGKSA-O

> <FORMULA>
C20H24NO4

> <MOLECULAR_WEIGHT>
342.414

> <EXACT_MASS>
342.169984677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.73592471715101

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
-1.3833977634717456

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.964239821387137

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.11151211902702

> <JCHEM_PKA_STRONGEST_BASIC>
-4.592988076925072

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
108.82809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-03 g/l

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

> <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+1
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  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   25                                                  
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   24                                             
CONECT   12   11    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21                                                       
CONECT   21   20                                                            
CONECT   22   16                                                            
CONECT   23   11                                                            
CONECT   24   11                                                            
CONECT   25    1                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
(+)-Magnoflorine	ChEBI
Magnoflorine	ChEBI
Magnoflorine iodide, (S)-isomer	MeSH
Magnoflorine perchlorate, (S)-isomer	MeSH

Chemical Formula

C₂₀H₂₄NO₄

Average Mass

342.4140 Da

Monoisotopic Mass

342.16998 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=C(C(O)=C(OC)C=C4)C3=C1O)[N+](C)(C)CC2

InChI Identifier

InChI=1S/C20H23NO4/c1-21(2)8-7-12-10-15(25-4)20(23)18-16(12)13(21)9-11-5-6-14(24-3)19(22)17(11)18/h5-6,10,13H,7-9H2,1-4H3,(H-,22,23)/p+1/t13-/m0/s1

InChI Key

YLRXAIKMLINXQY-ZDUSSCGKSA-O

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 callibotryon	Plant	KNApSAcK
Aconitum lycoctonum	LOTUS Database	35616633
Aconitum vulparia	Plant	KNApSAcK
Actaea racemosa	Plant	KNApSAcK
Actaea spicata	Plant	KNApSAcK
Anamirta cocculus	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Aquilegia alpina	LOTUS Database	35616633
Aquilegia coerulea	LOTUS Database	35616633
Aquilegia olympica	Plant	KNApSAcK
Argemone platyceras Link et Otto	Plant	KNApSAcK
Argemone polyanthemos	Plant	KNApSAcK
Argemone spp.	Plant	KNApSAcK
Aristolochia bracteolata	LOTUS Database	35616633
Aristolochia clematitis	Plant	KNApSAcK
Aristolochia contorta	Plant	KNApSAcK
Aristolochia cymbifera	LOTUS Database	35616633
Aristolochia debilis	Plant	KNApSAcK
Aristolochia elegans	Plant	KNApSAcK
Aristolochia fangchi	Plant	KNApSAcK
Aristolochia gigantea	Plant	KNApSAcK
Aristolochia heterophylla	Plant	KNApSAcK
Aristolochia indica	LOTUS Database	35616633
Aristolochia manshuriensis	Plant	KNApSAcK
Aristolochia moupinensis	Plant	KNApSAcK
Aristolochia sipho	Plant	KNApSAcK
Aristolochia thunbergii	Plant	KNApSAcK
Aristolochia triangularis	Plant	KNApSAcK
Asteropyrum cavaleriei	Plant	KNApSAcK
Berberis actinacantha	LOTUS Database	35616633
Berberis amurensis	Plant	KNApSAcK
Berberis aquifolium	LOTUS Database	35616633
Berberis crataegina	Plant	KNApSAcK
Berberis cretica	LOTUS Database	35616633
Berberis darwinii	LOTUS Database	35616633
Berberis heteropoda	LOTUS Database	35616633
Berberis iliensis	Plant	KNApSAcK
Berberis integerrima	Plant	KNApSAcK
Berberis kawakamii	Plant	KNApSAcK
Berberis nummularia	LOTUS Database	35616633
Berberis numularis	Plant	KNApSAcK
Berberis thunbergii	Plant	KNApSAcK
Berberis vulgaris	Plant	KNApSAcK
Caltha palustris	Plant	KNApSAcK
Caulophyllum thalicroides	Plant	KNApSAcK
Caulophyllum thalictroides	Plant	KNApSAcK
Chelidonium spp.	Plant	KNApSAcK
Cissampelos pareira	Plant	KNApSAcK
Clematis parviloba	Plant	KNApSAcK
Cocculus carolinus	Plant	KNApSAcK
Cocculus hirsutus	LOTUS Database	35616633
Cocculus trilobus	Plant	KNApSAcK
Consolida regalis	LOTUS Database	35616633
Coptis chinensis	Plant	KNApSAcK
Coptis deltoidea	Plant	KNApSAcK
Coptis japonica	Plant	KNApSAcK
Coptis quinquefolia	LOTUS Database	35616633
Coptis teetoides	Plant	KNApSAcK
Corydalis bungeana	Plant	KNApSAcK
Corydalis intermedia	Plant	KNApSAcK
Corydalis spp.	Plant	KNApSAcK
Croton cumingii	Plant	KNApSAcK
Croton lechleri	LOTUS Database	35616633
Croton lechleri Mull.Arg.	Plant	KNApSAcK
Croton menthodorus	LOTUS Database	35616633
Cymbopetalum brasiliense	LOTUS Database	35616633
Delphinium fangshanense W.T.	Plant	KNApSAcK
Delphinium pentagynum	Plant	KNApSAcK
Dicranostigma spp.	Plant	KNApSAcK
Dilphinium caeruleum	-	KNApSAcK
Dioscoreophyllum cumminsii	LOTUS Database	35616633
Diploclisia glaucescens	Plant	KNApSAcK
Epimedium brevicornum	Plant	KNApSAcK
Eschscholzia californica	Plant	KNApSAcK
Eschscholzia spp.	Plant	KNApSAcK
Fumaria capreolata	LOTUS Database	35616633
Glaucium arabicum	Plant	KNApSAcK
Glaucium fimbrilligerum	LOTUS Database	35616633
Glaucium flavum	Plant	KNApSAcK
Glaucium spp.	Plant	KNApSAcK
Glaucium squamigerum	LOTUS Database	35616633
Hernandia nymphaeifolia	LOTUS Database	35616633
Hypecoum procumbens	LOTUS Database	35616633
Hypserpa nitida	LOTUS Database	35616633
Isopyrum thalictroides	LOTUS Database	35616633
Litsea deccanensis	Plant	KNApSAcK
Magnolia accuminata	Plant	KNApSAcK
Magnolia denudata	Plant	KNApSAcK
Magnolia grandiflora	Plant	KNApSAcK
Magnolia kobus	Plant	KNApSAcK
Magnolia officinalis	Plant	KNApSAcK
Magnolia soulangeana	Plant	KNApSAcK
Magnolia speciosa	Plant	KNApSAcK
Mahonia fortunei	Plant	KNApSAcK
Mahonia japonica	Plant	KNApSAcK
Meconopsis cambrica	Plant	KNApSAcK
Meconopsis robusta	Plant	KNApSAcK
Meconopsis spp.	Plant	KNApSAcK
Menispermum canadense	LOTUS Database	35616633
Monodora junodii	Plant	KNApSAcK
Monodora tenuifolia	LOTUS Database	35616633
Nandina domestica	LOTUS Database	35616633
Pachygone ovata	LOTUS Database	35616633
Papaver bracteatum	LOTUS Database	35616633
Papaver glaucum	LOTUS Database	35616633
Papaver orientale	Plant	KNApSAcK
Papaver pavoninum	LOTUS Database	35616633
Papaver rhoeas	Plant	KNApSAcK
Papaver setigerum	Plant	KNApSAcK
Papaver somniferum	Plant	KNApSAcK
Papaver spp.	Plant	KNApSAcK
Paraquilegia anemonoides	Plant	KNApSAcK
Phellodendron amurense	Plant	KNApSAcK
Phellodendron chinense	Plant	KNApSAcK
Phellodendron chinense var.glabriusculum	Plant	KNApSAcK
Podophyllum peltatum	Plant	KNApSAcK
Potentilla discolor	Plant	KNApSAcK
Ranunculus serbicus	Plant	KNApSAcK
Rhigiocarya racemifera Miers	LOTUS Database	35616633
Semiaquilegia adoxoides	LOTUS Database	35616633
Sinomenium acutum	Plant	KNApSAcK
Stephania cephalantha	Plant	KNApSAcK
Stephania elegans	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633
Stylophorum diphyllum	LOTUS Database	35616633
Stylophorum lasiocarpum	Plant	KNApSAcK
Thalictrum aquilegifolium	LOTUS Database	35616633
Thalictrum baicalense	Plant	KNApSAcK
Thalictrum cultratum	LOTUS Database	35616633
Thalictrum dasycarpum	Plant	KNApSAcK
Thalictrum delavayi	Plant	KNApSAcK
Thalictrum flavum	Plant	KNApSAcK
Thalictrum foetidum	Plant	KNApSAcK
Thalictrum foliolosum	Plant	KNApSAcK
Thalictrum foliosum	Plant	KNApSAcK
Thalictrum isopyroides	Plant	KNApSAcK
Thalictrum javanicum Blume	LOTUS Database	35616633
Thalictrum longipedunculatum	Plant	KNApSAcK
Thalictrum lucidum	LOTUS Database	35616633
Thalictrum minums	Plant	KNApSAcK
Thalictrum minus	Plant	KNApSAcK
Thalictrum minus var. hypoleucum	Plant	KNApSAcK
Thalictrum petaloideum	LOTUS Database	35616633
Thalictrum podocarpum	LOTUS Database	35616633
Thalictrum przewalskii	Plant	KNApSAcK
Thalictrum simplex	LOTUS Database	35616633
Thalictrum symplex	Plant	KNApSAcK
Thalictrum thalictroides	Plant	KNApSAcK
Thalictrum urbainii	LOTUS Database	35616633
Thalictrum wangii	Plant	KNApSAcK
Tinospora capillipes	LOTUS Database	35616633
Tinospora cordifolia	Plant	KNApSAcK
Tinospora crispa	Plant	KNApSAcK
Tinospora malabrica	Plant	KNApSAcK
Toddalia asiatica	LOTUS Database	35616633
Xylopia parviflora	Plant	KNApSAcK
Xylopia vieillardi	Plant	KNApSAcK
Zanthoxylum austrosinense	LOTUS Database	35616633
Zanthoxylum chalybeum	Plant	KNApSAcK
Zanthoxylum gilletii	LOTUS Database	35616633
Zanthoxylum mayu	LOTUS Database	35616633
Zanthoxylum myriacanthum	Plant	KNApSAcK
Zanthoxylum nitidum	Plant	KNApSAcK
Zanthoxylum piperitum	LOTUS Database	35616633
Zanthoxylum rhoifolium	LOTUS Database	35616633
Zanthoxylum scandens	LOTUS Database	35616633
Zanthoxylum spp.	Plant	KNApSAcK
Zanthoxylum usambarense	LOTUS Database	35616633
Zanthoxylum usambarensis	Plant	KNApSAcK
Ziziphus jujuba	LOTUS Database	35616633
Zizyphus jujuba var. spinosa	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-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
Quaternary ammonium salt
Tetraalkylammonium salt
Azacycle
Ether
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Organic salt
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:6641 )
Isoquinoline alkaloids (C09581 )

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	0.74	ALOGPS
logP	-1.4	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.83 m³·mol⁻¹	ChemAxon
Polarizability	37.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Magnoflorine

METLIN ID

Not Available

PubChem Compound

73337

PDB ID

Not Available

ChEBI ID

6641

Good Scents ID

Not Available

References

General References

Ablajan N, Zhao B, Wenjuan X, Zhao J, Sagdullaev SS, Guoan Z, Aisa HA: Chemical components of Aconitum barbatum var. puberulum and their cytotoxic and antibacterial activities. Nat Prod Res. 2021 Nov 22:1-4. doi: 10.1080/14786419.2021.2005050. [PubMed:34802347 ]
Fu J, Jia Q, Liang P, Wang S, Zhou H, Zhang L, Gao C, Wang H, Lv Y, Han S: Targeting and Covalently Immobilizing the EGFR through SNAP-Tag Technology for Screening Drug Leads. Anal Chem. 2021 Aug 31;93(34):11719-11728. doi: 10.1021/acs.analchem.1c01664. Epub 2021 Aug 20. [PubMed:34415741 ]
Ahmad JB, Ajani EO, Sabiu S: Chemical Group Profiling, In Vitro and In Silico Evaluation of Aristolochia ringens on alpha-Amylase and alpha-Glucosidase Activity. Evid Based Complement Alternat Med. 2021 Jun 4;2021:6679185. doi: 10.1155/2021/6679185. eCollection 2021. [PubMed:34194523 ]
Deng Z, Yan Y, Zhao B, Wang R, Wang X, Chen H, Wen B: Identification of the active ingredients from Guangtongxiao decoction in rat bile based on ultra-performance liquid chromatography/Synapt G2 quadrupole time-of-flight tandem mass spectrometry. J Tradit Chin Med. 2020 Dec;40(6):999-1006. doi: 10.19852/j.cnki.jtcm.2020.06.011. [PubMed:33258352 ]

Showing NP-Card for (+)-Magnoflorine (NP0051001)

MOL for NP0051001 ((+)-Magnoflorine)

3D MOL for NP0051001 ((+)-Magnoflorine)

3D SDF for NP0051001 ((+)-Magnoflorine)

3D-SDF for NP0051001 ((+)-Magnoflorine)

PDB for NP0051001 ((+)-Magnoflorine)

3D PDB for NP0051001 ((+)-Magnoflorine)

SMILES for NP0051001 ((+)-Magnoflorine)

INCHI for NP0051001 ((+)-Magnoflorine)

Structure for NP0051001 ((+)-Magnoflorine)

3D Structure for NP0051001 ((+)-Magnoflorine)