NP-MRD: Showing NP-Card for Rosmarinine N-oxide (NP0068318)

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Record Information

Version

2.0

Created at

2022-04-28 13:27:41 UTC

Updated at

2026-02-22 16:00:44 UTC

NP-MRD ID

NP0068318

Natural Product DOI

https://doi.org/10.57994/8016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rosmarinine N-oxide

Description

(1R,4Z,6R,7R,11S,12S,17R)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14λ⁵-azatricyclo[9.5.1.0¹⁴,¹⁷]Heptadecane-3,8,14-trione belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. Rosmarinine N-oxide is found in Senecio runcinatus and Werneria nubigena . Based on a literature review very few articles have been published on (1R,4Z,6R,7R,11S,12S,17R)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14λ⁵-azatricyclo[9.5.1.0¹⁴,¹⁷]Heptadecane-3,8,14-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215272D          

 26 28  0  0  1  0            999 V2000
    1.9692   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -2.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -2.7273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9137   -2.2630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2547   -1.5094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626   -1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -1.5117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9748   -1.4402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179   -1.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791   -0.2591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5833    0.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -0.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1429   -1.1878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8248   -1.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637   -2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4456   -2.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844   -3.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -2.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -3.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8860   -0.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6919    0.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0284   -0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9618   -1.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 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  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
 15 23  1  1  0  0  0
 14 24  1  6  0  0  0
 14 25  1  1  0  0  0
  8 26  1  6  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    1.8808    4.3846    0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5233    3.1230    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    1.8979    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638    0.7346    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -0.4130   -0.4635 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8487   -1.0180   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664   -1.5533    0.5671 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3907   -2.0811    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876   -0.9426    1.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.6451    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285   -3.4913   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796   -2.7680    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1313   -1.7260    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5239   -1.2827   -0.5758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7489   -2.1231   -0.9973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9129   -2.1035   -2.3638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356   -1.2569   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139    0.0853   -0.5460 N   0  0  1  0  0  4  0  0  0  0  0  0
   -4.1459    0.6387   -1.5417 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5551    0.9565    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606    2.0366    0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    1.2579   -0.3221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4365    1.1415    0.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    1.8936    1.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    2.7188    2.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9767    0.0635   -0.8740 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7890    4.3562    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111    5.1979    0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882    4.6465    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    3.1352   -0.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    0.3413    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5122    1.0821   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -0.1235   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -0.3880   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909   -2.0341   -1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -0.9090   -2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1493   -1.4562    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5880   -2.1221    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4785   -3.1276    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -1.5455    2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.0096    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0077   -2.1856    1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -1.5734   -1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228   -3.1179   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170   -3.0088   -2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8308   -1.4727   -0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9245   -1.4613    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496    0.4880    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    1.4169    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821    2.7112   -0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116    2.5961    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827    1.9071   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970    0.1289   -2.0131 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
 15 17  1  0
 17 18  1  0
 18 19  1  6
 18 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
 24  3  1  0
 26 14  1  0
 26 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  6
 15 44  1  1
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  6
 26 53  1  6
M  CHG  2  18   1  19  -1
M  END


  Mrv1652304282215272D          

 26 28  0  0  1  0            999 V2000
    1.9692   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -2.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -2.7273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9137   -2.2630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2547   -1.5094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626   -1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -1.5117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9748   -1.4402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179   -1.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791   -0.2591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5833    0.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -0.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1429   -1.1878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8248   -1.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637   -2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4456   -2.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844   -3.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -2.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -3.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8860   -0.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6919    0.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0284   -0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9618   -1.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 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  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
 15 23  1  1  0  0  0
 14 24  1  6  0  0  0
 14 25  1  1  0  0  0
  8 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0068318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[C@@H](C)[C@@](C)(O)C(=O)OC[C@H]2[C@H](O)CN3(=O)CC[C@@H](OC1=O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO7/c1-4-11-7-10(2)18(3,23)17(22)25-9-12-13(20)8-19(24)6-5-14(15(12)19)26-16(11)21/h4,10,12-15,20,23H,5-9H2,1-3H3/b11-4-/t10-,12+,13-,14-,15-,18-,19?/m1/s1

> <INCHI_KEY>
QTCRXZRCLRRRCO-LVBFENQHSA-N

> <FORMULA>
C18H27NO7

> <MOLECULAR_WEIGHT>
369.414

> <EXACT_MASS>
369.178752213

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.77475813694012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,6R,7R,11S,12S,17R)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14lambda5-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8,14-trione

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-0.23696946566666593

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.832285381527377

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.356951716973704

> <JCHEM_PKA_STRONGEST_BASIC>
0.3404155201463399

> <JCHEM_POLAR_SURFACE_AREA>
119.94000000000001

> <JCHEM_REFRACTIVITY>
91.8884

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,6R,7R,11S,12S,17R)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14lambda5-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.676  -2.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.785  -4.005   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.978  -5.091   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.705  -4.224   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.342  -2.818   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       2.567  -1.267   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.864  -1.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.354  -2.822   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.820  -2.688   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.207  -2.019   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.321  -0.484   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.708   0.185   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.822   1.721   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.981  -0.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.867  -2.217   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.140  -3.084   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.026  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.298  -5.486   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.184  -7.022   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.638  -5.289   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.524  -6.824   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.366  -4.422   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.254  -1.548   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.892   0.560   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.520  -0.742   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.795  -3.364   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6    7                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   24   25                                             
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3                                                       
CONECT   23   15                                                            
CONECT   24   14                                                            
CONECT   25   14                                                            
CONECT   26    8                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₇NO₇

Average Mass

369.4140 Da

Monoisotopic Mass

369.17875 Da

IUPAC Name

(1R,4Z,6R,7R,11S,12S,17R)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14lambda5-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8,14-trione

Traditional Name

(1R,4Z,6R,7R,11S,12S,17R)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14lambda5-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8,14-trione

CAS Registry Number

Not Available

SMILES

C\C=C1\C[C@@H](C)[C@@](C)(O)C(=O)OC[C@H]2[C@H](O)CN3(=O)CC[C@@H](OC1=O)[C@@H]23

InChI Identifier

InChI=1S/C18H27NO7/c1-4-11-7-10(2)18(3,23)17(22)25-9-12-13(20)8-19(24)6-5-14(15(12)19)26-16(11)21/h4,10,12-15,20,23H,5-9H2,1-3H3/b11-4-/t10-,12+,13-,14-,15-,18-,19?/m1/s1

InChI Key

QTCRXZRCLRRRCO-LVBFENQHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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
Senecio hadiensis		Not Available
Senecio runcinatus	Plant	KNApSAcK
Werneria nubigena	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
N-alkylpyrrolidine
Dicarboxylic acid or derivatives
Trialkyl amine oxide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Pyrrolidine
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Trisubstituted n-oxide
Carboxylic acid derivative
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-0.74	ALOGPS
logP	-0.24	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.94 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.89 m³·mol⁻¹	ChemAxon
Polarizability	37.77 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163184401

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1016/0031-9422(93)85187-v

Showing NP-Card for Rosmarinine N-oxide (NP0068318)

MOL for NP0068318 (Rosmarinine N-oxide)

3D MOL for NP0068318 (Rosmarinine N-oxide)

3D SDF for NP0068318 (Rosmarinine N-oxide)

3D-SDF for NP0068318 (Rosmarinine N-oxide)

PDB for NP0068318 (Rosmarinine N-oxide)

3D PDB for NP0068318 (Rosmarinine N-oxide)

SMILES for NP0068318 (Rosmarinine N-oxide)

INCHI for NP0068318 (Rosmarinine N-oxide)

Structure for NP0068318 (Rosmarinine N-oxide)

3D Structure for NP0068318 (Rosmarinine N-oxide)