NP-MRD: Showing NP-Card for (+)-Stepharine (NP0067510)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 12:21:45 UTC

Updated at

2022-04-28 12:21:45 UTC

NP-MRD ID

NP0067510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Stepharine

Description

Stepharine, also known as ai3-34587, belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. Stepharine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-Stepharine is found in Abuta grandifolia, Abuta pahni (Martius) Krukoff & Barneby, Anamirta cocculum, Anamirta cocculus (L.)Wight & Arn. , Annona cherimola , Annona glabra , Annona muricata , Annona purpurea , Anomianthus dulcis , Artabotrys hexapetalus, Artabotrys uncinatus , Artebotrys uncinatus, Cocculus laurifolius, Cocculus laurifolius DC., Diploclisia glaucescens Diels , Glossocalyx brevipes, Greenwayodendron oliveri, Legnephora moorei, Legnephora moorei Miers, Limacia oblonga (Miers)Hook.& Thoms., Meiogyne monosperma, Meiogyne virgata, Menispermum dauricum, Menispermum dauricum DC. , Monodora tenuifolia, Neolitsea konishii, Oncodostigma monosperma, Porcelia macrocarpa, Sarcopetalum harveyanum F.Muell., Sciadotenia eichleriana Miers, Sinomenium acutum , Sinomonium acutum, Stephania bancroftii Bailey, Stephania cephalantha, Stephania cepharantha Hayata , Stephania glabra Miers , Stephania hainanensis H.S.Lo & Y., Stephania intermedia, Stephania intermedia H.S.Lo., Stephania venosa, Stephania venosa (Bl.) Spreng., Stephania venosa Spreng, Stephania yunnanensis, Stephania yunnanensis H.S Lo, Uvaria dulcis, Xylopia parviflora and Ziziphus jujuba . (+)-Stepharine was first documented in 2018 (PMID: 29782649). Based on a literature review a small amount of articles have been published on stepharine (PMID: 33007731) (PMID: 32991579) (PMID: 30781887) (PMID: 30453785).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.0884   -1.4377   -1.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204   -0.3501   -1.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -0.6236   -0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -1.9207   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3379   -2.1287    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0246    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124    0.2469   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1549    0.4541   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.7714   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349    2.5009    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205    1.1467    0.3332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5288    2.0184   -0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091    3.3175   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774    4.0064    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4516    5.2602    0.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    3.1960    1.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955    1.8770    1.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114    0.1777    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7910   -1.1448    0.8055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4393   -2.2893    0.3075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6703   -3.4108   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -3.4406    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -1.0860   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156   -1.9679   -0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6838   -2.1193   -2.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2419   -2.7674   -0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637    2.1460    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626    3.5992    0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    2.3766    0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7044    1.5143   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8445    3.8551   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006    3.7190    2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7646    1.3454    2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0471    0.5932    1.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035    0.1509   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630   -1.1737    1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -2.5679    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715   -3.6028   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -4.3388    0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258   -3.6706    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892   -4.2076   -0.2475 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 19  1  0
 19 18  1  0
 11 18  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22  5  1  0
  7  6  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
 19 36  1  1
 18 34  1  0
 18 35  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END


  Mrv1652304282214212D          

 22 25  0  0  1  0            999 V2000
    2.2721    0.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192    1.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017    1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2193    1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545    0.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450   -0.3569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0657   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -0.7800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5679   -1.1984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7765    0.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950   -0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0199   -0.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7884   -1.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0018    1.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1666    2.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665    2.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1488    3.0170    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
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  1  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
  2 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@@H](CC4(C=CC(=O)C=C4)C3=C1OC)NCC2

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-21-14-9-11-5-8-19-13-10-18(6-3-12(20)4-7-18)16(15(11)13)17(14)22-2/h3-4,6-7,9,13,19H,5,8,10H2,1-2H3/t13-/m1/s1

> <INCHI_KEY>
OGJKMZVUJJYWKO-CYBMUJFWSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.354

> <EXACT_MASS>
297.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.771130235196317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4'R)-10',11'-dimethoxy-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
2.0738404246666664

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.85648102656963

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
86.9753

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4'R)-10',11'-dimethoxy-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <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       4.241   0.084   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.088   1.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.396   2.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.856   3.102   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.009   2.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.702   0.572   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.617  -0.666   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.723  -1.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.254  -1.456   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.927  -2.237   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.587  -1.478   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.574   0.062   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.376   0.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.916   0.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.697  -0.641   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.237  -0.628   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.938  -1.981   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.398  -1.993   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.470   2.569   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.778   4.078   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.164   4.611   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.011   5.632   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13   18                                             
CONECT    8    7    9                                                       
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    7                                                       
CONECT   19    5   20                                                       
CONECT   20   19                                                            
CONECT   21    4   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
(+)-Stepharine	ChEBI
(R)-Stepharine	ChEBI
AI3-34587	ChEBI
Stepharine monohydrochloride	MeSH
Stepharine tosylate	MeSH

Chemical Formula

C₁₈H₁₉NO₃

Average Mass

297.3540 Da

Monoisotopic Mass

297.13649 Da

IUPAC Name

(4'R)-10',11'-dimethoxy-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

Traditional Name

(4'R)-10',11'-dimethoxy-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@@H](CC4(C=CC(=O)C=C4)C3=C1OC)NCC2

InChI Identifier

InChI=1S/C18H19NO3/c1-21-14-9-11-5-8-19-13-10-18(6-3-12(20)4-7-18)16(15(11)13)17(14)22-2/h3-4,6-7,9,13,19H,5,8,10H2,1-2H3/t13-/m1/s1

InChI Key

OGJKMZVUJJYWKO-CYBMUJFWSA-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
Abuta grandifolia	LOTUS Database	35616633
Abuta pahni (Martius) Krukoff & Barneby	Plant	KNApSAcK
Anamirta cocculum	Plant	KNApSAcK
Anamirta cocculus	Plant	KNApSAcK
Annona cherimola	Plant	KNApSAcK
Annona glabra	Plant	KNApSAcK
Annona muricata	Plant	KNApSAcK
Annona purpurea	Plant	KNApSAcK
Anomianthus dulcis	Plant	KNApSAcK
Artabotrys hexapetalus	LOTUS Database	35616633
Artabotrys uncinatus	Plant	KNApSAcK
Artebotrys uncinatus	-	KNApSAcK
Cocculus laurifolius	LOTUS Database	35616633
Cocculus laurifolius DC.	Plant	KNApSAcK
Diploclisia glaucescens Diels	Plant	KNApSAcK
Glossocalyx brevipes	LOTUS Database	35616633
Greenwayodendron oliveri	LOTUS Database	35616633
Legnephora moorei	LOTUS Database	35616633
Legnephora moorei Miers	Plant	KNApSAcK
Limacia oblonga (Miers)Hook.& Thoms.	Plant	KNApSAcK
Meiogyne monosperma	LOTUS Database	35616633
Meiogyne virgata	LOTUS Database	35616633
Menispermum dauricum	LOTUS Database	35616633
Menispermum dauricum DC.	Plant	KNApSAcK
Monodora tenuifolia	LOTUS Database	35616633
Neolitsea konishii	Plant	KNApSAcK
Oncodostigma monosperma	Plant	KNApSAcK
Porcelia macrocarpa	Plant	KNApSAcK
Sarcopetalum harveyanum F.Muell.	Plant	KNApSAcK
Sciadotenia eichleriana Miers	Plant	KNApSAcK
Sinomenium acutum	Plant	KNApSAcK
Sinomonium acutum	-	KNApSAcK
Stephania bancroftii Bailey	Plant	KNApSAcK
Stephania cephalantha	LOTUS Database	35616633
Stephania cepharantha Hayata	Plant	KNApSAcK
Stephania glabra Miers	Plant	KNApSAcK
Stephania hainanensis H.S.Lo & Y.	Plant	KNApSAcK
Stephania intermedia	Plant	KNApSAcK
Stephania intermedia H.S.Lo.	Plant	KNApSAcK
Stephania venosa	LOTUS Database	35616633
Stephania venosa (Bl.) Spreng.	Plant	KNApSAcK
Stephania venosa Spreng	Plant	KNApSAcK
Stephania yunnanensis	LOTUS Database	35616633
Stephania yunnanensis H.S Lo	Plant	KNApSAcK
Uvaria dulcis	LOTUS Database	35616633
Xylopia parviflora	Plant	KNApSAcK
Ziziphus jujuba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Proaporphines

Sub Class

Not Available

Direct Parent

Proaporphines

Alternative Parents

Substituents

Proaporphine
Tetrahydroisoquinoline
Indane
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Ketone
Cyclic ketone
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.76	ALOGPS
logP	2.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.98 m³·mol⁻¹	ChemAxon
Polarizability	31.77 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

C00025272

Chemspider ID

168085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193686

PDB ID

Not Available

ChEBI ID

132715

Good Scents ID

Not Available

References

General References

Hao T, Yang Y, Li N, Mi Y, Zhang G, Song J, Liang Y, Xiao J, Zhou D, He D, Hou Y: Inflammatory mechanism of cerebral ischemia-reperfusion injury with treatment of stepharine in rats. Phytomedicine. 2020 Dec;79:153353. doi: 10.1016/j.phymed.2020.153353. Epub 2020 Sep 22. [PubMed:33007731 ]
da Silva Mesquita R, Kyrylchuk A, Costa de Oliveira R, Costa Sa IS, Coutinho Borges Camargo G, Soares Pontes G, Moura Araujo da Silva F, Saraiva Nunomura RC, Grafov A: Alkaloids of Abuta panurensis Eichler: In silico and in vitro study of acetylcholinesterase inhibition, cytotoxic and immunomodulatory activities. PLoS One. 2020 Sep 29;15(9):e0239364. doi: 10.1371/journal.pone.0239364. eCollection 2020. [PubMed:32991579 ]
Gorpenchenko TY, Grigorchuk VP, Bulgakov DV, Tchernoded GK, Bulgakov VP: Tempo-Spatial Pattern of Stepharine Accumulation in Stephania Glabra Morphogenic Tissues. Int J Mol Sci. 2019 Feb 13;20(4). pii: ijms20040808. doi: 10.3390/ijms20040808. [PubMed:30781887 ]
Majrashi TA, Zulfiqar F, Chittiboyina AG, Ali Z, Khan IA: Isoquinoline alkaloids from Asimina triloba. Nat Prod Res. 2019 Oct;33(19):2823-2829. doi: 10.1080/14786419.2018.1504045. Epub 2018 Nov 20. [PubMed:30453785 ]
Xin A, Zhang Y, Zhang Y, Di D, Liu J: Development of an HPLC-DAD method for the determination of five alkaloids in Stephania yunnanensis Lo and in rat plasma after oral dose of Stephania yunnanensis Lo extracts. Biomed Chromatogr. 2018 Oct;32(10):e4292. doi: 10.1002/bmc.4292. Epub 2018 Jun 11. [PubMed:29782649 ]

Showing NP-Card for (+)-Stepharine (NP0067510)

MOL for NP0067510 ((+)-Stepharine)

3D MOL for NP0067510 ((+)-Stepharine)

3D SDF for NP0067510 ((+)-Stepharine)

3D-SDF for NP0067510 ((+)-Stepharine)

PDB for NP0067510 ((+)-Stepharine)

3D PDB for NP0067510 ((+)-Stepharine)

SMILES for NP0067510 ((+)-Stepharine)

INCHI for NP0067510 ((+)-Stepharine)

Structure for NP0067510 ((+)-Stepharine)

3D Structure for NP0067510 ((+)-Stepharine)