NP-MRD: Showing NP-Card for (1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione (NP0199943)

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Record Information

Version

2.0

Created at

2022-09-04 18:40:50 UTC

Updated at

2022-09-04 18:40:50 UTC

NP-MRD ID

NP0199943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

Description

Platyphylline 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,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione is found in Adenostyles alliariae, Leucanthemum vulgare, Cynoglossum officinale, Jacobaea boissieri, Jacobaea cilicia, Lotononis fruticoides, Pericallis aurita, Pittocaulon praecox, Senecio bollei, Jacobaea othonnae, Senecio triangularis and Senecio vernalis. (1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione was first documented in 2020 (PMID: 32419051). Based on a literature review a small amount of articles have been published on Platyphylline (PMID: 33488944) (PMID: 34185104) (PMID: 33389211) (PMID: 35948427).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    0.7648    4.4275    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3218    3.1264    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    2.0586    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324    0.7617    0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -0.0696   -0.3591 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4618    0.4512   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2549   -1.5122    0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7059   -1.8821    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871   -1.7526    1.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -2.3367   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -3.1065   -1.6180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -2.2480   -1.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6289   -2.1868   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299   -1.7735   -1.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9895   -2.6243   -0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855   -1.7544    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4043   -0.5836    0.7454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401    0.6384    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6149    1.6503    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9566    0.8185   -1.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6331    1.1096   -1.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113    2.1122   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    3.2014   -1.5840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4542   -0.4753   -0.7244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3088    4.3322    0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8339    5.1147    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    4.8956   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.0388    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    0.2259    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882    0.9618    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4235    0.0355   -1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806    1.5729   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044    0.1946   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3267    0.0959   -0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694   -2.9404    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1383   -1.2822    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -1.9286   -0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501   -2.4104    1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -3.2145    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -1.5163    0.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111   -2.0018   -2.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8563   -2.6583   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -3.5992   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3090   -1.3873    0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803   -2.3111    1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5836    0.9828    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1304    0.5691    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111    2.3965    0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458    2.1394   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190    1.1413   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5737   -0.4971   -0.9247 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  0
  7  9  1  1
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  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  2  0
 20 24  1  0
 22  3  1  0
 24 14  1  0
 24 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  6
  6 32  1  0
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 24 51  1  1
M  END


  Mrv1652309042220402D          

 24 26  0  0  1  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  1  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  1  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    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  1  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  1  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  1  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  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  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
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0199943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[C@@H](C)[C@@](C)(O)C(=O)OC[C@H]2CCN3CC[C@@H](OC1=O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4,11,13-15,22H,5-10H2,1-3H3/b12-4-/t11-,13-,14-,15-,18-/m1/s1

> <INCHI_KEY>
BTHCJHQOYFUIMG-REYNEDSXSA-N

> <FORMULA>
C18H27NO5

> <MOLECULAR_WEIGHT>
337.416

> <EXACT_MASS>
337.188922973

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.6627443837457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,6R,7R,11S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8-dione

> <JCHEM_LOGP>
1.7012301736666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.372490146156444

> <JCHEM_PKA_STRONGEST_BASIC>
8.991527493846764

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
88.84279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,6R,7R,11S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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  C   UNK     0      13.572   1.542   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.155  -0.350   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   24  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   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
CONECT   24   20   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
3-Ethylidenedodecahydro-5-hydroxy-5,5-dimethyl-1,6- dioxacyclododecino(2,3,4GH)pyrrolizine-2,7-dione	MeSH
Platyphylline hydrochloride	MeSH
Platyphylline, (1alpha,15E)-isomer	MeSH

Chemical Formula

C₁₈H₂₇NO₅

Average Mass

337.4160 Da

Monoisotopic Mass

337.18892 Da

IUPAC Name

(1R,4Z,6R,7R,11S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8-dione

Traditional Name

(1R,4Z,6R,7R,11S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8-dione

CAS Registry Number

Not Available

SMILES

C\C=C1\C[C@@H](C)[C@@](C)(O)C(=O)OC[C@H]2CCN3CC[C@@H](OC1=O)[C@@H]23

InChI Identifier

InChI=1S/C18H27NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4,11,13-15,22H,5-10H2,1-3H3/b12-4-/t11-,13-,14-,15-,18-/m1/s1

InChI Key

BTHCJHQOYFUIMG-REYNEDSXSA-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
Adenostyles alliariae	LOTUS Database	35616633
Chrysanthemum vulgare	LOTUS Database	35616633
Cynoglossum officinale	LOTUS Database	35616633
Jacobaea boissieri	LOTUS Database	35616633
Jacobaea cilicia	LOTUS Database	35616633
Lotononis fruticoides	LOTUS Database	35616633
Pericallis aurita	LOTUS Database	35616633
Pittocaulon praecox	LOTUS Database	35616633
Senecio bollei	LOTUS Database	35616633
Senecio othonnae	LOTUS Database	35616633
Senecio triangularis	LOTUS Database	35616633
Senecio vernalis	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

Macrolide
Pyrrolizidine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

macrolide (CHEBI:8264 )
Pyrrolizidine alkaloids (C10363 )

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	1.7	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	8.99	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.84 m³·mol⁻¹	ChemAxon
Polarizability	35.66 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

C00002107

Chemspider ID

4445056

KEGG Compound ID

C10363

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281742

PDB ID

Not Available

ChEBI ID

8264

Good Scents ID

Not Available

References

General References

Zheng P, Xu Y, Ren Z, Wang Z, Wang S, Xiong J, Zhang H, Jiang H: Toxic Prediction of Pyrrolizidine Alkaloids and Structure-Dependent Induction of Apoptosis in HepaRG Cells. Oxid Med Cell Longev. 2021 Jan 2;2021:8822304. doi: 10.1155/2021/8822304. eCollection 2021. [PubMed:33488944 ]
Buchmueller J, Sprenger H, Ebmeyer J, Rasinger JD, Creutzenberg O, Schaudien D, Hengstler JG, Guenther G, Braeuning A, Hessel-Pras S: Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Arch Toxicol. 2021 Aug;95(8):2785-2796. doi: 10.1007/s00204-021-03108-x. Epub 2021 Jun 29. [PubMed:34185104 ]
Zheng P, Peng T, Wang J, Zhang J, Wang Z, Zhang Y, Ren Z, Wang S, Jiang H: Fluorescent lateral flow immunoassay based on gold nanocluster for detection of pyrrolizidine alkaloids. Mikrochim Acta. 2021 Jan 3;188(1):11. doi: 10.1007/s00604-020-04672-2. [PubMed:33389211 ]
Taenzer J, Gehling M, Klevenhusen F, Saltzmann J, Danicke S, These A: Rumen Metabolism of Senecio Pyrrolizidine Alkaloids May Explain Why Cattle Tolerate Higher Doses Than Monogastric Species. J Agric Food Chem. 2022 Aug 24;70(33):10111-10120. doi: 10.1021/acs.jafc.2c01332. Epub 2022 Aug 10. [PubMed:35948427 ]
Ebmeyer J, Rasinger JD, Hengstler JG, Schaudien D, Creutzenberg O, Lampen A, Braeuning A, Hessel-Pras S: Hepatotoxic pyrrolizidine alkaloids induce DNA damage response in rat liver in a 28-day feeding study. Arch Toxicol. 2020 May;94(5):1739-1751. doi: 10.1007/s00204-020-02779-2. Epub 2020 May 17. [PubMed:32419051 ]
LOTUS database [Link]

Showing NP-Card for (1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione (NP0199943)

MOL for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

3D MOL for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

3D SDF for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

3D-SDF for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

PDB for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

3D PDB for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

SMILES for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

INCHI for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

Structure for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)

3D Structure for NP0199943 ((1r,4z,6r,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione)