NP-MRD: Showing NP-Card for Stephaphylline (NP0067559)

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Record Information

Version

2.0

Created at

2022-04-28 12:25:22 UTC

Updated at

2022-04-28 12:25:22 UTC

NP-MRD ID

NP0067559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stephaphylline

Description

Runanine belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane. Stephaphylline is found in Stephania sinica, Stephania suberosa and Stephania suberosa Forman. Stephaphylline was first documented in 2009 (PMID: 19072324). Based on a literature review a small amount of articles have been published on Runanine (PMID: 33523640) (PMID: 26521650) (PMID: 21638524) (PMID: 30548073).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214252D          

 27 30  0  0  1  0            999 V2000
    0.1905   -0.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.7035    0.0000 C   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  1  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 27  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.5961    1.7205    1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2287    0.3856    1.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8758    0.1296    1.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.1941    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484   -0.2713   -0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4155   -1.2306   -0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -0.4672   -0.1680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6996   -1.8871    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395   -2.1726    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.1751    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -1.5219    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673   -0.6044   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1742   -1.0014   -0.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5203   -2.3479   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550    0.7237   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5263    1.6731   -0.4752 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1079    3.0198   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    1.0791    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    0.1596    0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1546    0.5286    0.6338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5923    1.8054   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691    1.3852   -1.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265   -0.0432   -1.5162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3652   -0.6926   -2.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282    0.5681    2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258    0.2127    2.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936   -0.0169    3.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6719    1.8193    1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2174    2.4166    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    1.9291    2.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0208   -1.1261   -1.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943   -1.2124   -0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8898   -2.2279   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.3463    0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636   -2.4710   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332   -3.1758    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.2602    1.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548   -2.5836    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -2.9071   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1473   -2.7587    0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6346   -2.4750   -0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    3.1095   -1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587    3.6950   -0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6157    3.3277    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    2.1377   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    2.6591    0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5514    2.0986    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533    1.5267   -1.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573    1.9491   -2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496   -1.6299   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654    0.0404   -3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6364   -0.9439   -3.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010    0.0058    2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029    1.6386    2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 23  1  6
 23 24  1  0
 23 22  1  0
 22 21  1  0
 20 21  1  6
 20 25  1  0
 25 26  1  0
 26 27  2  0
 26  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
 10 11  2  0
 11 12  1  0
 20 19  1  0
 20  7  1  0
  7  4  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  0
  8 35  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
 22 48  1  0
 22 49  1  0
 21 46  1  0
 21 47  1  0
 25 53  1  0
 25 54  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
 11 38  1  0
M  END


  Mrv1652304282214252D          

 27 30  0  0  1  0            999 V2000
    0.1905   -0.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.7035    0.0000 C   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  1  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(CC[C@]34N(C)CC[C@]23CC(=O)C(OC)=C4OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO5/c1-22-9-8-20-12-15(23)18(26-4)19(27-5)21(20,22)7-6-13-10-16(24-2)17(25-3)11-14(13)20/h10-11H,6-9,12H2,1-5H3/t20-,21+/m0/s1

> <INCHI_KEY>
FFKKIUDOINNTGR-LEWJYISDSA-N

> <FORMULA>
C21H27NO5

> <MOLECULAR_WEIGHT>
373.449

> <EXACT_MASS>
373.188922973

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.24550155469177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S)-4,5,11,12-tetramethoxy-17-methyl-17-azatetracyclo[8.4.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,11-tetraen-13-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.4962315396666668

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.468748864142718

> <JCHEM_PKA_STRONGEST_BASIC>
7.444629450689925

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
103.90479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S)-4,5,11,12-tetramethoxy-17-methyl-17-azatetracyclo[8.4.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,11-tetraen-13-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       0.356  -0.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.897  -1.022   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.428  -2.245   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.770  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.850  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.390  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.160  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.390  -2.874   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850  -2.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -4.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.540  -4.207   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.700  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.470  -2.874   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.160   1.127   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.390   2.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.770  -0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.770  -0.206   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.540   1.127   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.540  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.770  -2.874   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.540  -4.207   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.770  -5.541   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.080  -1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.850  -0.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.143  -3.180   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5   13   22                                             
CONECT    5    4    1    6   18                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    4                                                       
CONECT   14    9   15                                                       
CONECT   15   14                                                            
CONECT   16    8   17                                                       
CONECT   17   16                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21    4   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25                                                            
CONECT   27    3                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₇NO₅

Average Mass

373.4490 Da

Monoisotopic Mass

373.18892 Da

IUPAC Name

(1S,10S)-4,5,11,12-tetramethoxy-17-methyl-17-azatetracyclo[8.4.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,11-tetraen-13-one

Traditional Name

(1S,10S)-4,5,11,12-tetramethoxy-17-methyl-17-azatetracyclo[8.4.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,11-tetraen-13-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(CC[C@]34N(C)CC[C@]23CC(=O)C(OC)=C4OC)=C1

InChI Identifier

InChI=1S/C21H27NO5/c1-22-9-8-20-12-15(23)18(26-4)19(27-5)21(20,22)7-6-13-10-16(24-2)17(25-3)11-14(13)20/h10-11H,6-9,12H2,1-5H3/t20-,21+/m0/s1

InChI Key

FFKKIUDOINNTGR-LEWJYISDSA-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
Stephania sinica	LOTUS Database	35616633
Stephania suberosa	LOTUS Database	35616633
Stephania suberosa Forman	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Hasubanan alkaloids

Sub Class

Not Available

Direct Parent

Hasubanan alkaloids

Alternative Parents

Substituents

Hasubanan skeleton
Phenanthrene
Tetralin
Indole or derivatives
Anisole
Cyclohexenone
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Vinylogous ester
Tertiary aliphatic amine
Cyclic ketone
Tertiary amine
Ketone
Organoheterocyclic compound
Ether
Azacycle
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
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	2.11	ALOGPS
logP	1.5	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	18.47	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	40.25 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

C00025123

Chemspider ID

52085761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119026174

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsu IT, Tomanik M, Herzon SB: Metric-Based Analysis of Convergence in Complex Molecule Synthesis. Acc Chem Res. 2021 Feb 16;54(4):903-916. doi: 10.1021/acs.accounts.0c00817. Epub 2021 Feb 1. [PubMed:33523640 ]
King SM, Herzon SB: The Hasubanan and Acutumine Alkaloids. Alkaloids Chem Biol. 2014;73:161-222. doi: 10.1016/B978-0-12-411565-1.00003-2. Epub 2013 Dec 25. [PubMed:26521650 ]
Herzon SB, Calandra NA, King SM: Efficient entry to the hasubanan alkaloids: first enantioselective total syntheses of (-)-hasubanonine, (-)-runanine, (-)-delavayine, and (+)-periglaucine B. Angew Chem Int Ed Engl. 2011 Sep 12;50(38):8863-6. doi: 10.1002/anie.201102226. Epub 2011 Jun 3. [PubMed:21638524 ]
Tan S, Li F, Park S, Kim S: Memory of Chirality in Bromoalkyne Carbocyclization: Applications in Asymmetric Total Synthesis of Hasubanan Alkaloids. Org Lett. 2019 Jan 4;21(1):292-295. doi: 10.1021/acs.orglett.8b03740. Epub 2018 Dec 14. [PubMed:30548073 ]
Nielsen DK, Nielsen LL, Jones SB, Toll L, Asplund MC, Castle SL: Synthesis of isohasubanan alkaloids via enantioselective ketone allylation and discovery of an unexpected rearrangement. J Org Chem. 2009 Feb 6;74(3):1187-99. doi: 10.1021/jo802370v. [PubMed:19072324 ]

Showing NP-Card for Stephaphylline (NP0067559)

MOL for NP0067559 (Stephaphylline)

3D MOL for NP0067559 (Stephaphylline)

3D SDF for NP0067559 (Stephaphylline)

3D-SDF for NP0067559 (Stephaphylline)

PDB for NP0067559 (Stephaphylline)

3D PDB for NP0067559 (Stephaphylline)

SMILES for NP0067559 (Stephaphylline)

INCHI for NP0067559 (Stephaphylline)

Structure for NP0067559 (Stephaphylline)

3D Structure for NP0067559 (Stephaphylline)