NP-MRD: Showing NP-Card for (1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione (NP0239598)

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Record Information

Version

2.0

Created at

2022-09-06 23:13:50 UTC

Updated at

2022-09-06 23:13:50 UTC

NP-MRD ID

NP0239598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione

Description

Amphidinolide N belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione was first documented in 2016 (PMID: 27116189). Based on a literature review a small amount of articles have been published on amphidinolide N (PMID: 33769047) (PMID: 33390515) (PMID: 30457857) (PMID: 26844805).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201132D          

 45 47  0  0  1  0            999 V2000
    2.2838   -0.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -0.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870    0.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791    0.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4013    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8711    1.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537    0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2235    0.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
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 11 13  1  0  0  0  0
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 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
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 16 22  1  0  0  0  0
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 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
  2 45  1  0  0  0  0
 43 45  1  0  0  0  0
M  END

     RDKit          3D

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 19 65  1  6
 20 66  1  0
 20 67  1  0
 21 68  1  0
 21 69  1  0
 22 70  1  6
 23 71  1  0
 24 72  1  0
 24 73  1  0
 25 74  1  6
 26 75  1  0
 27 76  1  0
 27 77  1  0
 28 78  1  0
 28 79  1  0
 29 80  1  1
 30 81  1  0
M  END


  Mrv1652309072201132D          

 45 47  0  0  1  0            999 V2000
    2.2838   -0.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -0.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870    0.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791    0.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4013    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8711    1.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537    0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2235    0.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9282   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584   -1.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7504   -0.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028   -1.5144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6330   -2.1925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5727   -0.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2774   -2.3281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0996   -2.3960    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5694   -1.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2171   -0.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949   -0.9040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0425   -0.1581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4520   -3.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9822   -3.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3345   -4.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1599   -3.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901   -4.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8679   -4.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3981   -5.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155   -3.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457   -4.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2235   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537   -4.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314   -4.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -3.5488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409   -2.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8108   -2.1247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187   -2.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489   -3.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -1.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6362   -1.3109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3442   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219   -1.8534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918   -1.1753    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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  6  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
  2 45  1  0  0  0  0
 43 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC1OC(=O)C(C)C(O)C2OC2C(=C)C(O)CC(=O)C(C)\C=C(C)\C[C@@H](O)[C@]2(O)O[C@H](CC[C@H]2O)CC(O)CCC1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H54O12/c1-6-7-8-26-23(35)11-9-21(34)15-22-10-12-27(38)33(42,45-22)28(39)14-17(2)13-18(3)24(36)16-25(37)19(4)30-31(44-30)29(40)20(5)32(41)43-26/h13,18,20-23,25-31,34-35,37-40,42H,4,6-12,14-16H2,1-3,5H3/b17-13+/t18?,20?,21?,22-,23?,25?,26?,27-,28-,29?,30?,31?,33-/m1/s1

> <INCHI_KEY>
RGZICDGNHLJCDN-CRWBKOJESA-N

> <FORMULA>
C33H54O12

> <MOLECULAR_WEIGHT>
642.783

> <EXACT_MASS>
642.361527179

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
68.76481095609103

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4E,24R,27R)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0^{11,13}]octacos-4-ene-7,16-dione

> <JCHEM_LOGP>
1.4177440189999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.230904618817291

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.226703655463021

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7232170435809007

> <JCHEM_POLAR_SURFACE_AREA>
206.73999999999998

> <JCHEM_REFRACTIVITY>
163.53150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4E,24R,27R)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0^{11,13}]octacos-4-ene-7,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.263  -1.055   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.728  -0.928   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.071   0.464   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.536   0.591   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.948   1.730   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.482   1.604   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.359   2.870   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.140   0.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.017   1.477   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.675   0.085   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.333  -1.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.456  -2.574   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.867  -1.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.525  -2.827   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.648  -4.093   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.060  -2.953   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.402  -1.561   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.718  -4.346   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.253  -4.472   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.130  -3.207   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.472  -1.814   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.937  -1.688   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.279  -0.295   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.910  -5.865   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.033  -7.131   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.691  -8.523   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.499  -7.004   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.622  -8.270   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.087  -8.143   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.210  -9.409   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.429  -6.751   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.552  -8.017   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.017  -7.890   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.140  -9.156   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.605  -9.030   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.894  -6.624   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.236  -5.232   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.113  -3.966   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.702  -5.105   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.825  -6.371   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.044  -3.713   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.921  -2.447   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.509  -3.586   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.974  -3.460   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.851  -2.194   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   45                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   31   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43   45                                                       
CONECT   45   44    2   43                                                  
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₅₄O₁₂

Average Mass

642.7830 Da

Monoisotopic Mass

642.36153 Da

IUPAC Name

(1R,2R,4E,24R,27R)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0^{11,13}]octacos-4-ene-7,16-dione

Traditional Name

(1R,2R,4E,24R,27R)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0^{11,13}]octacos-4-ene-7,16-dione

CAS Registry Number

Not Available

SMILES

CCCCC1OC(=O)C(C)C(O)C2OC2C(=C)C(O)CC(=O)C(C)\C=C(C)\C[C@@H](O)[C@]2(O)O[C@H](CC[C@H]2O)CC(O)CCC1O

InChI Identifier

InChI=1S/C33H54O12/c1-6-7-8-26-23(35)11-9-21(34)15-22-10-12-27(38)33(42,45-22)28(39)14-17(2)13-18(3)24(36)16-25(37)19(4)30-31(44-30)29(40)20(5)32(41)43-26/h13,18,20-23,25-31,34-35,37-40,42H,4,6-12,14-16H2,1-3,5H3/b17-13+/t18?,20?,21?,22-,23?,25?,26?,27-,28-,29?,30?,31?,33-/m1/s1

InChI Key

RGZICDGNHLJCDN-CRWBKOJESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Oxane
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Oxirane
Polyol
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.42	ChemAxon
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	206.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	163.53 m³·mol⁻¹	ChemAxon
Polarizability	68.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

8207667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10032097

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ohta M, Kato S, Sugai T, Fuwa H: Cobalt-Catalyzed Hartung-Mukaiyama Cyclization of gamma-Hydroxy Olefins: Stereocontrolled Synthesis of the Tetrahydrofuran Moiety of Amphidinolide N. J Org Chem. 2021 Apr 16;86(8):5584-5615. doi: 10.1021/acs.joc.1c00085. Epub 2021 Mar 26. [PubMed:33769047 ]
Tsuda M, Akakabe M, Minamida M, Kumagai K, Tsuda M, Konishi Y, Tominaga A, Fukushi E, Kawabata J: Structure and Stereochemistry of Amphidinolide N Congeners from Marine Dinoflagellate Amphidinium Species. Chem Pharm Bull (Tokyo). 2021;69(1):141-149. doi: 10.1248/cpb.c20-00745. [PubMed:33390515 ]
Trost BM, Bai WJ, Stivala CE, Hohn C, Poock C, Heinrich M, Xu S, Rey J: Enantioselective Synthesis of des-Epoxy-Amphidinolide N. J Am Chem Soc. 2018 Dec 12;140(49):17316-17326. doi: 10.1021/jacs.8b11827. Epub 2018 Dec 4. [PubMed:30457857 ]
Kawashima Y, Toyoshima A, Fuwa H, Sasaki M: Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment. Org Lett. 2016 May 6;18(9):2232-5. doi: 10.1021/acs.orglett.6b00871. Epub 2016 Apr 26. [PubMed:27116189 ]
Ochiai K, Kuppusamy S, Yasui Y, Harada K, Gupta NR, Takahashi Y, Kubota T, Kobayashi J, Hayashi Y: Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis. Chemistry. 2016 Mar 1;22(10):3287-3291. doi: 10.1002/chem.201504675. Epub 2016 Feb 4. [PubMed:26844805 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione (NP0239598)

MOL for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

3D MOL for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

3D SDF for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

3D-SDF for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

PDB for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

3D PDB for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

SMILES for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

INCHI for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

Structure for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)

3D Structure for NP0239598 ((1r,2r,4e,24r,27r)-18-butyl-1,2,9,14,19,22,27-heptahydroxy-4,6,15-trimethyl-10-methylidene-12,17,28-trioxatricyclo[22.3.1.0??,??]octacos-4-ene-7,16-dione)