NP-MRD: Showing NP-Card for (4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione (NP0286375)

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Record Information

Version

2.0

Created at

2022-09-09 14:55:15 UTC

Updated at

2022-09-09 14:55:15 UTC

NP-MRD ID

NP0286375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Description

RETRORSINE, also known as usaramine, 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. (4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione is found in Senecio brasiliensis. (4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione was first documented in 2021 (PMID: 35024309). Based on a literature review a significant number of articles have been published on RETRORSINE (PMID: 35917946) (PMID: 35737038) (PMID: 35700647) (PMID: 35598524) (PMID: 35370657) (PMID: 34941681).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216552D          

 25 27  0  0  0  0            999 V2000
    5.3780    3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 15 25  1  0  0  0  0
 18 25  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -1.7589    4.2525    0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639    2.8110    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    2.0025   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2361    0.5227   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143   -0.0741    0.2152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6176    0.0975   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501   -1.5402    0.4892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4868   -2.1853   -0.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2732   -1.9374    0.4737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048   -2.0414   -0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080   -1.4944   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4413    1.0884    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    1.0725   -0.8782 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1736    1.6033   -1.2833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.4623   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    3.7210   -1.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -0.2552   -1.1853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9151    4.7116   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986    4.7197    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0950    0.1949   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    0.2647    0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5272    0.3747   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -2.8830   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3487   -1.6801    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907   -1.4235    2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2294   -3.5290    2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -1.6438   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -3.1557   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080   -3.1162    0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2723   -1.7940   -0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3698    2.1159    1.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246    0.3598    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612    1.7767   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.3940   -2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 21 25  1  0
 23  3  1  0
 25 15  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  6
 25 50  1  6
M  END


  Mrv1652309092216552D          

 25 27  0  0  0  0            999 V2000
    5.3780    3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 15 25  1  0  0  0  0
 18 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-

> <INCHI_KEY>
BCJMNZRQJAVDLD-BASWHVEKSA-N

> <FORMULA>
C18H25NO6

> <MOLECULAR_WEIGHT>
351.399

> <EXACT_MASS>
351.168187529

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.519551195027695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_LOGP>
0.5969526486666659

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.971010053552853

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.442771664578194

> <JCHEM_PKA_STRONGEST_BASIC>
7.136049874699854

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
90.95029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.039   6.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.167   5.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.572   1.542   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.155  -0.350   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.383   0.579   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   11                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
CONECT   25   21   15   18                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Retrorsine hydrochloride	MeSH
Retrorsine, (15E)-isomer	MeSH
Usaramine	MeSH

Chemical Formula

C₁₈H₂₅NO₆

Average Mass

351.3990 Da

Monoisotopic Mass

351.16819 Da

IUPAC Name

(4Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

Traditional Name

(4Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

CAS Registry Number

Not Available

SMILES

C\C=C1\CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-

InChI Key

BCJMNZRQJAVDLD-BASWHVEKSA-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

Species Name	Source	Reference
Senecio brasiliensis	LOTUS Database	35616633

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

Senecionan-skeleton
Macrolide
Alkaloid or derivatives
Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Alcohol
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	0.6	ChemAxon
pKa (Strongest Acidic)	11.44	ChemAxon
pKa (Strongest Basic)	7.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	36.52 Å³	ChemAxon
Number of Rings	3	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

C00002109

Chemspider ID

4509313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li W, Cheng T, Jiang T, Zhou M, Gong B, Zhao G, Li J, Tan R, Yang X, Joshi K, Peng Y, Cheng M, Liu T, Wang DO, Zheng J: Hepatic RNA adduction derived from metabolic activation of retrorsine in vitro and in vivo. Chem Biol Interact. 2022 Sep 25;365:110047. doi: 10.1016/j.cbi.2022.110047. Epub 2022 Jul 30. [PubMed:35917946 ]
Zhu L, Xue J, He Y, Xia Q, Fu PP, Lin G: Correlation Investigation between Pyrrole-DNA and Pyrrole-Protein Adducts in Male ICR Mice Exposed to Retrorsine, a Hepatotoxic Pyrrolizidine Alkaloid. Toxins (Basel). 2022 May 28;14(6):377. doi: 10.3390/toxins14060377. [PubMed:35737038 ]
Xiao Y, Yi H, Wang G, Chen S, Li X, Wu Q, Zhang S, Deng K, He Y, Yang X: Electrochemiluminescence sensor for point-of-care detection of pyrrolizidine alkaloids. Talanta. 2022 Nov 1;249:123645. doi: 10.1016/j.talanta.2022.123645. Epub 2022 Jun 1. [PubMed:35700647 ]
Wang Z, Ma J, He Y, Miu KK, Yao S, Tang C, Ye Y, Lin G: Nrf2-mediated liver protection by 18beta-glycyrrhetinic acid against pyrrolizidine alkaloid-induced toxicity through PI3K/Akt/GSK3beta pathway. Phytomedicine. 2022 Jul 20;102:154162. doi: 10.1016/j.phymed.2022.154162. Epub 2022 May 13. [PubMed:35598524 ]
Wang Z, Ma J, Yao S, He Y, Miu KK, Xia Q, Fu PP, Ye Y, Lin G: Liquorice Extract and 18beta-Glycyrrhetinic Acid Protect Against Experimental Pyrrolizidine Alkaloid-Induced Hepatotoxicity in Rats Through Inhibiting Cytochrome P450-Mediated Metabolic Activation. Front Pharmacol. 2022 Mar 16;13:850859. doi: 10.3389/fphar.2022.850859. eCollection 2022. [PubMed:35370657 ]
He Y, Ma J, Fan X, Ding L, Ding X, Zhang QY, Lin G: The key role of gut-liver axis in pyrrolizidine alkaloid-induced hepatotoxicity and enterotoxicity. Acta Pharm Sin B. 2021 Dec;11(12):3820-3835. doi: 10.1016/j.apsb.2021.07.013. Epub 2021 Jul 21. [PubMed:35024309 ]
Pearson AJ, Nicolas JEF, Lancaster JE, Symes CW: Characterization and Lifetime Dietary Risk Assessment of Eighteen Pyrrolizidine Alkaloids and Pyrrolizidine Alkaloid N-Oxides in New Zealand Honey. Toxins (Basel). 2021 Nov 26;13(12):843. doi: 10.3390/toxins13120843. [PubMed:34941681 ]
Naito Y, Yoshinouchi Y, Sorayama Y, Kohara H, Kitano S, Irie S, Matsusaki M: Constructing vascularized hepatic tissue by cell-assembled viscous tissue sedimentation method and its application for vascular toxicity assessment. Acta Biomater. 2022 Mar 1;140:275-288. doi: 10.1016/j.actbio.2021.11.027. Epub 2021 Nov 24. [PubMed:34826641 ]
Enge AM, Kaltner F, Gottschalk C, Kin A, Kirstgen M, Geyer J, These A, Hammer H, Potz O, Braeuning A, Hessel-Pras S: Organic Cation Transporter I and Na(+) /taurocholate Co-Transporting Polypeptide are Involved in Retrorsine- and Senecionine-Induced Hepatotoxicity in HepaRG cells. Mol Nutr Food Res. 2022 Jan;66(2):e2100800. doi: 10.1002/mnfr.202100800. Epub 2021 Dec 11. [PubMed:34826203 ]
Ma J, Zhang C, He Y, Chen X, Lin G: Fasting augments pyrrolizidine alkaloid-induced hepatotoxicity. Arch Toxicol. 2022 Feb;96(2):639-651. doi: 10.1007/s00204-021-03193-y. Epub 2021 Nov 18. [PubMed:34792613 ]
Li J, Zhou M, Lai X, Wang Y, Zou Y, Li K, Li W, Zheng J: Toxicokinetic and bioavailability studies on retrorsine in mice, and ketoconazole-induced alteration in toxicokinetic properties. Biomed Chromatogr. 2022 Feb;36(2):e5270. doi: 10.1002/bmc.5270. Epub 2021 Nov 22. [PubMed:34727371 ]
Snyman T, Crowther NJ: The Detection of Toxic Compounds in Extracts of Callilepis laureola (Oxeye Daisy) and Senecio latifolius (Ragwort) by Ultra-Performance Liquid Chromatography-Mass Spectrometry (UPLC-MS/MS). Methods Mol Biol. 2022;2343:381-393. doi: 10.1007/978-1-0716-1558-4_28. [PubMed:34473339 ]
Zhu L, Zhang C, Zhang W, Xia Q, Ma J, He X, He Y, Fu PP, Jia W, Zhuge Y, Lin G: Developing urinary pyrrole-amino acid adducts as non-invasive biomarkers for identifying pyrrolizidine alkaloids-induced liver injury in human. Arch Toxicol. 2021 Oct;95(10):3191-3204. doi: 10.1007/s00204-021-03129-6. Epub 2021 Aug 14. [PubMed:34390356 ]
Zhang L, Ge JY, Zheng YW, Sun Z, Wang C, Peng Z, Wu B, Fang M, Furuya K, Ma X, Shao Y, Ohkohchi N, Oda T, Fan J, Pan G, Li D, Hui L: Survival-Assured Liver Injury Preconditioning (SALIC) Enables Robust Expansion of Human Hepatocytes in Fah(-/-) Rag2(-/-) IL2rg(-/-) Rats. Adv Sci (Weinh). 2021 Oct;8(19):e2101188. doi: 10.1002/advs.202101188. Epub 2021 Aug 11. [PubMed:34382351 ]
Guo L, Zhang L, Xu H, Yu P, Wang Z, Lu D, Chen M, Wu B: Diurnal hepatic CYP3A11 contributes to chronotoxicity of the pyrrolizidine alkaloid retrorsine in mice. Xenobiotica. 2021 Sep;51(9):1019-1028. doi: 10.1080/00498254.2021.1950867. Epub 2021 Jul 26. [PubMed:34311664 ]
LOTUS database [Link]

Showing NP-Card for (4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione (NP0286375)

MOL for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D MOL for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D SDF for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D-SDF for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

PDB for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D PDB for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

SMILES for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

INCHI for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

Structure for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D Structure for NP0286375 ((4z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)