NP-MRD: Showing NP-Card for (1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione (NP0324000)

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Record Information

Version

2.0

Created at

2022-09-12 03:47:47 UTC

Updated at

2022-09-12 03:47:47 UTC

NP-MRD ID

NP0324000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Description

Spartioidine belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. (1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione is found in Jacobaea aquatica, Jacobaea uniflora, Senecio inaequidens, Senecio pterophorus and Senecio vulgaris. (1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione was first documented in 2015 (PMID: 26411004). Based on a literature review very few articles have been published on Spartioidine (PMID: 28828276).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122205472D          

 24 26  0  0  1  0            999 V2000
    7.0069    0.9375    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
    6.8228    0.1333    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0315   -0.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660   -1.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 O   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
    5.9824    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9849    2.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127    1.3431    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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 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  2  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 16 24  1  0  0  0  0
 10 24  1  0  0  0  0
 13 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@H](OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO5/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/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4+/t14-,15?,18+/m0/s1

> <INCHI_KEY>
FCEVNJIUIMLVML-MIULREJOSA-N

> <FORMULA>
C18H23NO5

> <MOLECULAR_WEIGHT>
333.384

> <EXACT_MASS>
333.157622845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.179226770917516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4E,7R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_LOGP>
1.3741705343333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.03788353703767

> <JCHEM_PKA_STRONGEST_BASIC>
8.136016731918334

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
89.1071

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4E,7R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      13.080   1.750   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.520  -2.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.992  -1.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.920  -1.705   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.577  -3.206   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.792  -0.657   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.008   1.892   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.351   3.394   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.167   5.348   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.038   3.889   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.464   2.507   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   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16   10   13                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₃NO₅

Average Mass

333.3840 Da

Monoisotopic Mass

333.15762 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@H](OC1=O)C23

InChI Identifier

InChI=1S/C18H23NO5/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/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4+/t14-,15?,18+/m0/s1

InChI Key

FCEVNJIUIMLVML-MIULREJOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jacobaea aquatica	LOTUS Database	35616633
Jacobaea uniflora	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio pterophorus	LOTUS Database	35616633
Senecio vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Senecionan-skeleton
Alkaloid or derivatives
Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026183

Chemspider ID

30772502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91746605

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cheng D, Nguyen VT, Ndihokubwayo N, Ge J, Mulder PPJ: Pyrrolizidine alkaloid variation in Senecio vulgaris populations from native and invasive ranges. PeerJ. 2017 Aug 14;5:e3686. doi: 10.7717/peerj.3686. eCollection 2017. [PubMed:28828276 ]
Chizzola R: Pyrrolizidine Alkaloids in Adenostyles alliariae and A. glabra from the Austrian Alps. Nat Prod Commun. 2015 Jul;10(7):1179-80. [PubMed:26411004 ]
LOTUS database [Link]

Showing NP-Card for (1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione (NP0324000)

MOL for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D MOL for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D SDF for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D-SDF for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

PDB for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D PDB for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

SMILES for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

INCHI for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

Structure for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D Structure for NP0324000 ((1s,4e,7r)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)