NP-MRD: Showing NP-Card for Heilonine A (NP0332498)

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Record Information

Version

1.0

Created at

2024-02-13 01:04:16 UTC

Updated at

2024-04-19 10:09:37 UTC

NP-MRD ID

NP0332498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heilonine A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02132401042D          

 34 39  0  0  1  0            999 V2000
    5.0061    0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6530    0.1082    0.0000 C   0  0  2  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  1  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
    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  0  0  0  0  0  0  0  0  0  0
    3.9530   -1.1507    0.0000 C   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  0  0  0  0  0  0  0  0  0  0
    2.7459   -0.3860    0.0000 C   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
    6.4198    0.4125    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
    7.1866    0.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9535    1.0212    0.0000 O   0  0  0  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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  6  0  0  0
  9  7  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 20 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 16  1  0  0  0  0
 27 28  1  1  0  0  0
  3 29  1  1  0  0  0
  3 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END


  Mrv2104 02132401042D          

 34 39  0  0  1  0            999 V2000
    5.0061    0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6530    0.1082    0.0000 C   0  0  2  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  1  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
    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  0  0  0  0  0  0  0  0  0  0
    3.9530   -1.1507    0.0000 C   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  0  0  0  0  0  0  0  0  0  0
    2.7459   -0.3860    0.0000 C   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
    6.4198    0.4125    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
    7.1866    0.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9535    1.0212    0.0000 O   0  0  0  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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  6  0  0  0
  9  7  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 20 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 16  1  0  0  0  0
 27 28  1  1  0  0  0
  3 29  1  1  0  0  0
  3 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@H](O)[C@@]3([H])C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC1=C2C=CC2=C1CN1C[C@H](C)CC[C@@]1([H])[C@@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO2/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/h5-6,15-17,21,23-26,29-30H,4,7-14H2,1-3H3/t15-,16-,17+,21+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
BTAYCTHBBSLSCE-DZQXAYNJSA-N

> <FORMULA>
C27H39NO2

> <MOLECULAR_WEIGHT>
409.614

> <EXACT_MASS>
409.2980795

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.204698015388686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R,9S,10R,15R,17S,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosa-1(14),2(11),12-triene-17,20-diol

> <JCHEM_LOGP>
4.2057585206666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.416631746772357

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.744039335487718

> <JCHEM_PKA_STRONGEST_BASIC>
9.618852158745186

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
122.278

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R,9S,10R,15R,17S,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosa-1(14),2(11),12-triene-17,20-diol

> <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  C   UNK     0       9.345   1.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.552   0.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.760  -0.754   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.536  -2.277   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.744  -3.233   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.105  -2.845   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.897  -1.890   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       8.515  -3.382   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       9.121  -0.366   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      10.329  -1.322   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       7.741   0.317   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.664  -0.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.379  -2.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.555  -3.449   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.016  -3.386   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.302  -2.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.126  -0.721   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.411   0.644   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.872   0.707   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.048  -0.594   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.510  -0.531   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.205   0.833   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.619   2.134   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.096   3.498   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.158   2.071   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.224  -1.895   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       2.763  -1.958   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.939  -3.259   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      11.984   0.770   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      13.191  -0.186   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.415   1.338   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.846   1.906   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.207   2.294   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.776   1.726   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   34                                             
CONECT    3    2    4   29   30                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   26   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19                                                       
CONECT   26   20                                                            
CONECT   27   20   16   28                                                  
CONECT   28   27                                                            
CONECT   29    3                                                            
CONECT   30    3   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉NO₂

Average Mass

409.6140 Da

Monoisotopic Mass

409.29808 Da

IUPAC Name

(6R,9S,10R,15R,17S,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosa-1(14),2(11),12-triene-17,20-diol

Traditional Name

(6R,9S,10R,15R,17S,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosa-1(14),2(11),12-triene-17,20-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@H](O)[C@@]3([H])C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC1=C2C=CC2=C1CN1C[C@H](C)CC[C@@]1([H])[C@@H]2C

InChI Identifier

InChI=1S/C27H39NO2/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/h5-6,15-17,21,23-26,29-30H,4,7-14H2,1-3H3/t15-,16-,17+,21+,23+,24-,25+,26+,27-/m1/s1

InChI Key

BTAYCTHBBSLSCE-DZQXAYNJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	lijiayuan@simm.ac.cn	Not Available	Not Available	2024-02-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.771622357 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500.133088507 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	4.21	ChemAxon
pKa (Strongest Acidic)	14.74	ChemAxon
pKa (Strongest Basic)	9.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	122.28 m³·mol⁻¹	ChemAxon
Polarizability	50.2 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

Not Available

Showing NP-Card for Heilonine A (NP0332498)

MOL for NP0332498 (Heilonine A)

3D MOL for NP0332498 (Heilonine A)

3D SDF for NP0332498 (Heilonine A)

3D-SDF for NP0332498 (Heilonine A)

PDB for NP0332498 (Heilonine A)

3D PDB for NP0332498 (Heilonine A)

SMILES for NP0332498 (Heilonine A)

INCHI for NP0332498 (Heilonine A)

Structure for NP0332498 (Heilonine A)

3D Structure for NP0332498 (Heilonine A)