NP-MRD: Showing NP-Card for Integerrimine (NP0051165)

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Record Information

Version

2.0

Created at

2022-04-27 22:34:21 UTC

Updated at

2022-04-27 22:34:21 UTC

NP-MRD ID

NP0051165

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Integerrimine

Description

Senecionine, also known as intergerrimine or aureine, 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. The cytotoxicity was greater in the absence of extracellular Ca2+ than in its presence, suggesting that alterations in intracellular Ca2+ distribution, and not an influx of extracellular Ca2+, were responsible for the senecionine-induced hepatotoxicity. Senecionine is an organic compound with the chemical formula C18H25NO5. It is classified as a pyrrolizidine alkaloid. PAs are tumorigenic. Senecionine is classified as a pyrrolizidine alkaloid (PA). The pyrrolizidine alkaloid senecionine has been shown to produce an increase in cytosolic free Ca2+ concentration in isolated hepatocytes that correlated with an increase in cellular toxicity. Senecionine is a very strong basic compound (based on its pKa). Senecionine is a potentially toxic compound. Substantial research has revealed that senecionine-induced hepatotoxicity is associated with lipid peroxidation, intracellular Ca2+ alteration, and intercellular glutathione depletion. Senecionine has been shown to be hepatotoxic, genotoxic, and cytotoxic. Integerrimine is found in Ajuga parviflora, Cacalia hastata, Leucanthemum vulgare, Crotalaria brevidens , Crotalaria breviflora, Crotalaria brevifolia, Crotalaria incana , Crotalaria intermedia, Crotalaria juncea, Crotalaria micans, Crotalaria naragutensis , Crotalaria tetragona, Crotalaria trichotoma, Danaus plexippus, Emilia coccinea, Gynura japonica, Gynura procumbens, Jacobaea aquatica, Jacobaea arnautorum, Jacobaea leucophylla, Jessea multivenia, Liatris punctata, Ligularia japonica, Lotononis alpina, Lotononis azurea, Lotononis brevicaulis, Lotononis caerulescens, Lotononis divaricata, Lotononis elongata, Lotononis hirsuta, Lotononis longicephala, Lotononis lotononoides, Lotononis meyeri, Lotononis pulchella, Lotononis purpurascens, Lotononis rigida, Lotononis sericophylla, Lotononis trichodes, Melampyrum pratense, Osyris alba, Packera anonyma, Packera glabella, Packera multilobata, Pericallis aurita, Petasites hybridus , Pittocaulon filare, Pittocaulon praecox, Pittocaulon velatum, Senecio alpinus, Senecio brasiliensis, Jacobaea erucifolia, Senecio faberi, Senecio fistulosus, Senecio flaccidus, Senecio gallicus, Senecio glabellum, Senecio glaucus, Senecio ilicifolius, Senecio inaequidens, Senecio integerrimus, Jacobaea vulgaris, Senecio leucanthemifolius, Senecio longibolus, Senecio magnificus, Senecio mairetianus, Senecio malacitanus, Senecio miser, Senecio nebrodensis, Senecio nemorensis, Senecio pterophorus, Senecio rosmarinifolius, Senecio selloi, Senecio squalidus, Jacobaea subalpina, Packera tomentosa, Senecio triangularis, Senecio vernalis, Senecio viscosus, Senecio vulgaris, Snecio squalidus, Syneilesis palmata, Tussilago farfara and Werneria nubigena. Integerrimine was first documented in 1999 (PMID: 17260281). PAs also cause hepatic veno-occlusive disease and liver cancer (PMID: 15202562) (PMID: 21710732).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291400592D          

 28 30  0  0  1  0            999 V2000
    7.0589   -2.0367    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
    6.8507    2.1917    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
    3.2152    1.1725    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
    2.7199    0.5127    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
    6.8228    0.1333    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
    6.2184    0.6948    0.0000 C   0  0  2  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
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  2  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
    5.7982    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  1  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
    5.6660   -1.7177    0.0000 O   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
    7.1626    1.1780    0.0000 O   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
    5.2458   -0.3520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0315   -0.9899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6141    1.2564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9316   -1.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6269   -0.8264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  2  1  1  0  0  0
 11  9  1  0  0  0  0
 12  4  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 18  3  1  1  0  0  0
 18 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 18 22  1  6  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25  4  1  0  0  0  0
 11 26  1  6  0  0  0
 14 27  1  1  0  0  0
 15 28  1  1  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -1.7835    2.9097   -2.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1292    2.1354   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.5557   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    0.8008    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -0.4486    0.8671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8662   -0.2831    1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3647   -1.1205   -0.4334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7996   -2.5826   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4508   -0.5949   -1.1839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1491   -1.1948   -1.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930   -0.5448   -2.3076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0542   -1.9243   -0.8528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -1.9204    0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1242   -1.4921    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -1.7702   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850   -1.0613   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0797   -0.3221    0.5128 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    1.0893    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796    1.7289    1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    0.7402    1.0885 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2858    0.9315   -0.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    1.6971   -0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    2.6868   -1.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673   -0.5813    0.9968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3660    3.9072   -1.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033    2.2782   -2.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409    3.1110   -2.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    2.0325   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381    1.4952    1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    0.6428    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.2178    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    0.5634    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2893   -1.1951    1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4565   -0.0015    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071   -3.2585   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103   -2.9391   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147   -2.7136    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -1.1052   -2.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -2.9901    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -1.3501    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -2.4094   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629   -0.4496   -1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0830   -1.8220   -0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2479    1.4928   -0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2427    1.3342    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166    2.7311    0.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222    1.7430    2.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    0.7350    2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8823   -1.0487    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  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  6
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  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
  2 28  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  1
  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
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 24 49  1  1
M  END


  Mrv0541 08291400592D          

 28 30  0  0  1  0            999 V2000
    7.0589   -2.0367    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
    6.8507    2.1917    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
    3.2152    1.1725    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
    2.7199    0.5127    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
    6.8228    0.1333    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
    6.2184    0.6948    0.0000 C   0  0  2  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
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  2  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
    5.7982    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  1  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
    5.6660   -1.7177    0.0000 O   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
    7.1626    1.1780    0.0000 O   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
    5.2458   -0.3520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0315   -0.9899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6141    1.2564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9316   -1.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6269   -0.8264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  2  1  1  0  0  0
 11  9  1  0  0  0  0
 12  4  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 18  3  1  1  0  0  0
 18 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 18 22  1  6  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25  4  1  0  0  0  0
 11 26  1  6  0  0  0
 14 27  1  1  0  0  0
 15 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051165

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C1/C[C@@]([H])(C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@]([H])(OC1=O)[C@@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H25NO5/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/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1

> <INCHI_KEY>
HKODIGSRFALUTA-JTLQZVBZSA-N

> <FORMULA>
C18H25NO5

> <MOLECULAR_WEIGHT>
335.3948

> <EXACT_MASS>
335.173272915

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.84332232166074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.6438626153333336

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.370863309435826

> <JCHEM_PKA_STRONGEST_BASIC>
7.136068783494925

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
89.40659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
senecionine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      13.177  -3.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.788   4.091   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.520  -2.301   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.008   1.892   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.536   1.440   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       7.192  -0.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.920  -1.705   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      10.577  -3.206   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.167   5.348   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.370   2.199   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.351   3.394   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.792  -0.657   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      14.992  -1.848   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      10.480   2.345   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       9.206  -2.370   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.770  -1.543   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   11                                                            
CONECT    3   18                                                            
CONECT    4    1   12   25                                                  
CONECT    5    7   13                                                       
CONECT    6    8   14                                                       
CONECT    7    5   19                                                       
CONECT    8    6   19                                                       
CONECT    9   11   12                                                       
CONECT   10   13   23                                                       
CONECT   11    2    9   18   26                                             
CONECT   12    4    9   16                                                  
CONECT   13    5   10   15                                                  
CONECT   14    6   15   24   27                                             
CONECT   15   13   14   19   28                                             
CONECT   16   12   20   24                                                  
CONECT   17   18   21   23                                                  
CONECT   18    3   11   17   22                                             
CONECT   19    7    8   15                                                  
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   10   17                                                       
CONECT   24   14   16                                                       
CONECT   25    4                                                            
CONECT   26   11                                                            
CONECT   27   14                                                            
CONECT   28   15                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Aureine	ChEBI
Senecionin	ChEBI
Senecionine citratre	MeSH
Senecionine, (15E)-isomer	MeSH
Squalidine	MeSH
Senecionine citrate (1:1)	MeSH
Intergerrimine	MeSH
Integerrimine	MeSH

Chemical Formula

C₁₈H₂₅NO₅

Average Mass

335.3948 Da

Monoisotopic Mass

335.17327 Da

IUPAC Name

(1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Traditional Name

senecionine

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C1/C[C@@]([H])(C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@]([H])(OC1=O)[C@@]23[H]

InChI Identifier

InChI=1S/C18H25NO5/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/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1

InChI Key

HKODIGSRFALUTA-JTLQZVBZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ajuga parviflora	LOTUS Database	35616633
Cacalia hastata	Plant	KNApSAcK
Chrysanthemum vulgare	LOTUS Database	35616633
Crotalaria brevidens	Plant	KNApSAcK
Crotalaria breviflora	Plant	KNApSAcK
Crotalaria brevifolia	Plant	KNApSAcK
Crotalaria incana	Plant	KNApSAcK
Crotalaria intermedia	Plant	KNApSAcK
Crotalaria juncea	LOTUS Database	35616633
Crotalaria micans	LOTUS Database	35616633
Crotalaria naragutensis	Plant	KNApSAcK
Crotalaria tetragona	Plant	KNApSAcK
Crotalaria trichotoma	Plant	KNApSAcK
Danaus plexippus	LOTUS Database	35616633
Emilia coccinea	LOTUS Database	35616633
Gynura japonica	LOTUS Database	35616633
Gynura procumbens	LOTUS Database	35616633
Jacobaea aquatica	LOTUS Database	35616633
Jacobaea arnautorum	LOTUS Database	35616633
Jacobaea leucophylla	LOTUS Database	35616633
Jessea multivenia	LOTUS Database	35616633
Liatris punctata	LOTUS Database	35616633
Ligularia japonica	LOTUS Database	35616633
Lotononis alpina	Plant	KNApSAcK
Lotononis azurea	Plant	KNApSAcK
Lotononis brevicaulis	Plant	KNApSAcK
Lotononis caerulescens	Plant	KNApSAcK
Lotononis divaricata	Plant	KNApSAcK
Lotononis elongata	Plant	KNApSAcK
Lotononis hirsuta	Plant	KNApSAcK
Lotononis longicephala	Plant	KNApSAcK
Lotononis lotononoides	Plant	KNApSAcK
Lotononis meyeri	Plant	KNApSAcK
Lotononis pulchella	Plant	KNApSAcK
Lotononis purpurascens	Plant	KNApSAcK
Lotononis rigida	Plant	KNApSAcK
Lotononis sericophylla	Plant	KNApSAcK
Lotononis trichodes	Plant	KNApSAcK
Melampyrum pratense	LOTUS Database	35616633
Osyris alba	LOTUS Database	35616633
Packera anonyma	LOTUS Database	35616633
Packera glabella	LOTUS Database	35616633
Packera multilobata	LOTUS Database	35616633
Pericallis aurita	LOTUS Database	35616633
Petasites hybridus	Plant	KNApSAcK
Pittocaulon filare	Plant	KNApSAcK
Pittocaulon praecox	Plant	KNApSAcK
Pittocaulon velatum	Plant	KNApSAcK
Senecio alpinus	Plant	KNApSAcK
Senecio brasiliensis	Plant	KNApSAcK
Senecio erucifolius	LOTUS Database	35616633
Senecio faberi	Plant	KNApSAcK
Senecio fistulosus	LOTUS Database	35616633
Senecio flaccidus	LOTUS Database	35616633
Senecio gallicus	LOTUS Database	35616633
Senecio glabellum	Plant	KNApSAcK
Senecio glaucus	LOTUS Database	35616633
Senecio ilicifolius	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio integerrimus	Plant	KNApSAcK
Senecio jacobaea	LOTUS Database	35616633
Senecio leucanthemifolius	LOTUS Database	35616633
Senecio longibolus	Plant	KNApSAcK
Senecio magnificus	LOTUS Database	35616633
Senecio mairetianus	Plant	KNApSAcK
Senecio malacitanus	LOTUS Database	35616633
Senecio miser	Plant	KNApSAcK
Senecio nebrodensis	LOTUS Database	35616633
Senecio nemorensis	LOTUS Database	35616633
Senecio pterophorus	LOTUS Database	35616633
Senecio rosmarinifolius	LOTUS Database	35616633
Senecio selloi	LOTUS Database	35616633
Senecio squalidus	Plant	KNApSAcK
Senecio subalpinus	LOTUS Database	35616633
Senecio tomentosus	LOTUS Database	35616633
Senecio triangularis	LOTUS Database	35616633
Senecio vernalis	LOTUS Database	35616633
Senecio viscosus	LOTUS Database	35616633
Senecio vulgaris	LOTUS Database	35616633
Snecio squalidus	-	KNApSAcK
Syneilesis palmata	LOTUS Database	35616633
Tussilago farfara	LOTUS Database	35616633
Werneria nubigena	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
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
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:9107 )
lactone (CHEBI:9107 )
pyrrolizidine alkaloid (CHEBI:9107 )
Pyrrolizidine alkaloids (C06176 )

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	1.45	ALOGPS
logP	1.64	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	7.14	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	89.41 m³·mol⁻¹	ChemAxon
Polarizability	34.84 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

C00002116

Chemspider ID

Not Available

KEGG Compound ID

C06176

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Senecionine

METLIN ID

Not Available

PubChem Compound

5280906

PDB ID

Not Available

ChEBI ID

9107

Good Scents ID

Not Available

References

General References

Chung WG, Buhler DR: Differential metabolism of the pyrrolizidine alkaloid, senecionine, in Fischer 344 and Sprague-Dawley rats. Arch Pharm Res. 2004 May;27(5):547-53. doi: 10.1007/BF02980130. [PubMed:15202562 ]
Ndjoko K, Wolfender JL, Roder E, Hostettmann K: Determination of pyrrolizidine alkaloids in senecio species by liquid chromatography/thermospray-mass spectrometry and liquid chromatography/nuclear magnetic resonance spectroscopy. Planta Med. 1999 Aug;65(6):562-6. doi: 10.1055/s-1999-14027. [PubMed:17260281 ]
Xiong A, Yang L, Yang X, Wang C, Wang Z: [Simultaneous quantitation of adonifoline and senecionine in Senecio herbs by UPLC-MS]. Zhongguo Zhong Yao Za Zhi. 2011 Mar;36(6):702-5. [PubMed:21710732 ]

Showing NP-Card for Integerrimine (NP0051165)

MOL for NP0051165 (Integerrimine)

3D MOL for NP0051165 (Integerrimine)

3D SDF for NP0051165 (Integerrimine)

3D-SDF for NP0051165 (Integerrimine)

PDB for NP0051165 (Integerrimine)

3D PDB for NP0051165 (Integerrimine)

SMILES for NP0051165 (Integerrimine)

INCHI for NP0051165 (Integerrimine)

Structure for NP0051165 (Integerrimine)

3D Structure for NP0051165 (Integerrimine)