NP-MRD: Showing NP-Card for (1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione (NP0326842)

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Record Information

Version

2.0

Created at

2022-09-12 08:50:18 UTC

Updated at

2022-09-12 08:50:18 UTC

NP-MRD ID

NP0326842

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione

Description

Senecicannabine 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. (1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione is found in Jacobaea ambigua. (1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione was first documented in 2011 (PMID: 21506416). Based on a literature review very few articles have been published on Senecicannabine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210502D          

 26 30  0  0  1  0            999 V2000
    6.8462    2.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7298    1.8829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0373    1.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2206    1.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3386    0.1095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5219    0.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0311    0.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -0.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0468   -0.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921   -1.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567   -1.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.8316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076   -0.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9240    0.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749    0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4504    0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    2.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1932    2.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568    1.9446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8059    1.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6879    2.5597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3913    1.6371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  6  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 19  1  1  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -1.8194    3.7944    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1881    2.3368    0.7756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3415    1.4143    1.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.3515   -0.0260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2065    0.3276   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.8694    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9462   -0.8835    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.7773    0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3036   -2.1755   -0.6503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9766   -3.2949    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649   -2.5958   -1.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -2.0838   -1.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3731   -2.4116   -2.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629   -1.6557   -1.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -1.8900   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027   -1.2897   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1472   -1.6953   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2793   -0.7075   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666    0.4632   -0.5297 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858    1.5445    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    2.1651    0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6302    1.0537    0.5999 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9961    1.2904   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352    1.8324   -0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    2.7324   -1.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.1039    0.4797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2155    4.1716   -0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    3.9913    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3938    4.3539    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    2.1434    0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0731    0.8589   -1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871   -0.0128   -1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145   -0.0272    2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468   -1.8595    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9405   -3.7728    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -2.9501    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -4.0537   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -1.9539   -2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691   -2.9448    0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2654   -1.3544    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2063   -2.5601   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8381   -0.6694   -1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8753   -0.9945    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    1.2686    1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4313    2.3232   -0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988    3.0586    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8107    2.3659    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    1.0272    1.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1817   -0.2820    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  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  1  0
 24 25  2  0
 22 26  1  0
  4  2  1  0
 24  4  1  0
  6  8  1  6
 26 16  1  0
 26 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  1
 26 49  1  1
M  END


  Mrv1652309122210502D          

 26 30  0  0  1  0            999 V2000
    6.8462    2.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7298    1.8829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0373    1.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2206    1.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3386    0.1095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5219    0.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0311    0.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -0.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0468   -0.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921   -1.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567   -1.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.8316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076   -0.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9240    0.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749    0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4504    0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    2.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1932    2.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568    1.9446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8059    1.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6879    2.5597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3913    1.6371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  6  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0326842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC11C[C@]2(CO2)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO7/c1-10-18(26-10)8-17(9-24-17)16(2,22)14(20)23-7-11-3-5-19-6-4-12(13(11)19)25-15(18)21/h3,10,12-13,22H,4-9H2,1-2H3/t10-,12+,13+,16-,17-,18?/m0/s1

> <INCHI_KEY>
LTFQUYMOUGXPEW-SAUXSIBXSA-N

> <FORMULA>
C18H23NO7

> <MOLECULAR_WEIGHT>
365.382

> <EXACT_MASS>
365.147452085

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.47188738212569

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,3S,6'S,7'R,17'R)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0^{14,17}]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione

> <JCHEM_LOGP>
-0.4516449316666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.436175644277132

> <JCHEM_PKA_STRONGEST_BASIC>
6.922780630879975

> <JCHEM_POLAR_SURFACE_AREA>
101.13

> <JCHEM_REFRACTIVITY>
87.53119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,3S,6'S,7'R,17'R)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0^{14,17}]heptadecane-6',2''-oxiran]-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      12.780   5.039   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.562   3.515   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.136   2.086   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.612   2.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.394   0.778   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.965   0.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.441   0.422   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.391   1.633   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.748  -1.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.287  -1.270   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.065  -2.827   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.319  -1.894   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.102  -3.419   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.107  -0.944   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.325   0.581   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.113   1.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.574   1.588   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.153   3.069   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.431   3.928   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.961   5.374   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.500   5.317   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.759   3.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.971   2.679   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.400   3.254   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.617   4.778   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.330   3.056   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    4                                                       
CONECT    4    3    2    5   24                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6    8                                                       
CONECT    8    7    6                                                       
CONECT    9    6   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23    4   25                                                  
CONECT   25   24                                                            
CONECT   26   22   16   19                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₃NO₇

Average Mass

365.3820 Da

Monoisotopic Mass

365.14745 Da

IUPAC Name

(1'R,3S,6'S,7'R,17'R)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0^{14,17}]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione

Traditional Name

(1'R,3S,6'S,7'R,17'R)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0^{14,17}]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC11C[C@]2(CO2)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

InChI Identifier

InChI=1S/C18H23NO7/c1-10-18(26-10)8-17(9-24-17)16(2,22)14(20)23-7-11-3-5-19-6-4-12(13(11)19)25-15(18)21/h3,10,12-13,22H,4-9H2,1-2H3/t10-,12+,13+,16-,17-,18?/m0/s1

InChI Key

LTFQUYMOUGXPEW-SAUXSIBXSA-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
Jacobaea ambigua	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
N-alkylpyrrolidine
Dicarboxylic acid or derivatives
Tertiary alcohol
Pyrroline
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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
logP	-0.45	ChemAxon
pKa (Strongest Acidic)	11.44	ChemAxon
pKa (Strongest Basic)	6.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.53 m³·mol⁻¹	ChemAxon
Polarizability	35.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

139187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158192

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma H, Yang L, Wang C, Wang Z: [Pyrrolizidine alkaloids of Senecio cannabifolius var. integrilifolius]. Zhongguo Zhong Yao Za Zhi. 2011 Jan;36(2):166-8. [PubMed:21506416 ]
LOTUS database [Link]

Showing NP-Card for (1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione (NP0326842)

MOL for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

3D MOL for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

3D SDF for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

3D-SDF for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

PDB for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

3D PDB for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

SMILES for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

INCHI for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

Structure for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)

3D Structure for NP0326842 ((1'r,3s,6's,7'r,17'r)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione)