NP-MRD: Showing NP-Card for sinicanone A (NP0332496)

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Record Information

Version

1.0

Created at

2024-02-13 00:57:59 UTC

Updated at

2024-04-19 10:09:33 UTC

NP-MRD ID

NP0332496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sinicanone A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02132400582D          

 38 43  0  0  1  0            999 V2000
    7.9535    1.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1866    0.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5397    1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729    0.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6530    0.1082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0061    0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -0.4037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1802   -1.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133   -1.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7664   -1.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5619   -1.8117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8862   -0.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5332   -0.7081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1469    0.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -0.4199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1287   -1.1168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530   -1.1507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3192   -0.4114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -1.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3044   -1.0830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9216   -0.3522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459   -0.3860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1874    0.3109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3631    0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -0.3183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2730   -0.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.1433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0512    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559    1.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558   -1.0152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -1.0491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0386   -1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8271   -1.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9470   -0.9157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -0.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 12 10  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 21  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  1  0  0  0
 34 27  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  1  0  0  0
  8 36  2  0  0  0  0
  7 37  1  1  0  0  0
  7 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END


  Mrv2104 02132400582D          

 38 43  0  0  1  0            999 V2000
    7.9535    1.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1866    0.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5397    1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729    0.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6530    0.1082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0061    0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -0.4037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1802   -1.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133   -1.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7664   -1.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5619   -1.8117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8862   -0.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5332   -0.7081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1469    0.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -0.4199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1287   -1.1168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530   -1.1507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3192   -0.4114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -1.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3044   -1.0830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9216   -0.3522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459   -0.3860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1874    0.3109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3631    0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -0.3183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2730   -0.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.1433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0512    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559    1.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558   -1.0152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -1.0491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0386   -1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8271   -1.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9470   -0.9157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -0.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 12 10  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 21  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  1  0  0  0
 34 27  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  1  0  0  0
  8 36  2  0  0  0  0
  7 37  1  1  0  0  0
  7 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@]3([H])[C@@H](C)[C@]4([H])CC[C@@H](C)CN4C[C@@]3([H])[C@]1([H])C[C@@]1([H])[C@@]2([H])CC(=O)[C@@]2([H])C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO2/c1-15-4-7-25-16(2)18-5-6-19-20(22(18)14-28(25)13-15)11-23-21(19)12-26(30)24-10-17(29)8-9-27(23,24)3/h15-25,29H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21+,22-,23+,24-,25+,27-/m1/s1

> <INCHI_KEY>
MWBJDDYEYGDWCZ-PQELVAGOSA-N

> <FORMULA>
C27H43NO2

> <MOLECULAR_WEIGHT>
413.646

> <EXACT_MASS>
413.329379629

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.47279219118747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,9S,10R,11R,14S,15S,18S,20S,23R,24S)-20-hydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosan-17-one

> <JCHEM_LOGP>
4.301876046333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.234327012887148

> <JCHEM_PKA_STRONGEST_BASIC>
10.864012497881696

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
121.00739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,9S,10R,11R,14S,15S,18S,20S,23R,24S)-20-hydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-FEB-24         0                                  
HETATM    1  O   UNK     0      14.846   1.906   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      13.415   1.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.207   2.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.776   1.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.552   0.202   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.345   1.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.760  -0.754   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.536  -2.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.105  -2.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.897  -1.890   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       8.515  -3.382   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       9.121  -0.366   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      10.329  -1.322   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       7.741   0.317   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.664  -0.784   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.840  -2.085   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       7.379  -2.148   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       8.063  -0.768   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       6.555  -3.449   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.016  -3.386   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.302  -2.022   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.587  -0.657   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       5.126  -0.721   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       5.950   0.580   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       4.411   0.644   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.872   0.707   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       2.048  -0.594   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.510  -0.531   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.205   0.833   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.619   2.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.096   3.498   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.158   2.071   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       1.224  -1.895   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0       2.763  -1.958   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.939  -3.259   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.744  -3.233   0.000  0.00  0.00           O+0
HETATM   37  H   UNK     0      12.968  -1.709   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0      13.191  -0.186   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8   37   38                                             
CONECT    8    7    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   34                                             
CONECT   22   21                                                            
CONECT   23   21   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   33   34                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26                                                       
CONECT   33   27                                                            
CONECT   34   27   21   35                                                  
CONECT   35   34                                                            
CONECT   36    8                                                            
CONECT   37    7                                                            
CONECT   38    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₃NO₂

Average Mass

413.6460 Da

Monoisotopic Mass

413.32938 Da

IUPAC Name

(1R,2S,6R,9S,10R,11R,14S,15S,18S,20S,23R,24S)-20-hydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosan-17-one

Traditional Name

(1R,2S,6R,9S,10R,11R,14S,15S,18S,20S,23R,24S)-20-hydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosan-17-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@]3([H])[C@@H](C)[C@]4([H])CC[C@@H](C)CN4C[C@@]3([H])[C@]1([H])C[C@@]1([H])[C@@]2([H])CC(=O)[C@@]2([H])C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H43NO2/c1-15-4-7-25-16(2)18-5-6-19-20(22(18)14-28(25)13-15)11-23-21(19)12-26(30)24-10-17(29)8-9-27(23,24)3/h15-25,29H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21+,22-,23+,24-,25+,27-/m1/s1

InChI Key

MWBJDDYEYGDWCZ-PQELVAGOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.929467415 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17360102 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	4.3	ChemAxon
pKa (Strongest Acidic)	15.23	ChemAxon
pKa (Strongest Basic)	10.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.01 m³·mol⁻¹	ChemAxon
Polarizability	50.47 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

Not Available

Showing NP-Card for sinicanone A (NP0332496)

MOL for NP0332496 (sinicanone A)

3D MOL for NP0332496 (sinicanone A)

3D SDF for NP0332496 (sinicanone A)

3D-SDF for NP0332496 (sinicanone A)

PDB for NP0332496 (sinicanone A)

3D PDB for NP0332496 (sinicanone A)

SMILES for NP0332496 (sinicanone A)

INCHI for NP0332496 (sinicanone A)

Structure for NP0332496 (sinicanone A)

3D Structure for NP0332496 (sinicanone A)