NP-MRD: Showing NP-Card for Symphytine (NP0137587)

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Record Information

Version

2.0

Created at

2022-05-30 16:57:00 UTC

Updated at

2022-05-30 16:57:00 UTC

NP-MRD ID

NP0137587

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Symphytine

Description

Symphytine 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. Symphytine is a very strong basic compound (based on its pKa). Symphytine is found in Myosotis scorpioides, Pulmonaria obscura, Symphytum officinale and Symphytum uplandicum. Symphytine was first documented in 1979 (PMID: 287835). A but-2-enoate ester obtained by formal condensation of the carboxy group of (2E)-2-methylbut-2-enoic acid with the 1-hydroxy group of (1R,7aR)-7-({oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol (PMID: 11430014) (PMID: 15482618) (PMID: 17401847) (PMID: 6579012).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004201615532D          

 31 32  0  0  1  0            999 V2000
    3.8585   -2.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127   -0.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626   -1.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019   -2.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0258   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827   -2.3068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9007   -0.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -1.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -2.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4527    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -1.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -1.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -0.5436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -0.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -1.7698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -1.7547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554   -0.1709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    1.1524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  2  0  0  0  0
 14  5  1  0  0  0  0
 15  7  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  6  0  0  0
 21  9  1  0  0  0  0
 21 10  1  0  0  0  0
 21 17  1  0  0  0  0
 14 22  1  1  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
 20 25  1  6  0  0  0
 26 11  1  0  0  0  0
 26 19  1  0  0  0  0
 16 27  1  1  0  0  0
 27 18  1  0  0  0  0
 28  6  1  0  0  0  0
 14 29  1  1  0  0  0
 16 30  1  6  0  0  0
 17 31  1  6  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
    4.4483    3.3699    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9812    1.9927    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946    0.9563    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2064    1.1931    0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3681   -0.3949   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515   -1.3768   -0.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0449   -0.6762   -0.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -1.9913   -0.7362 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1033   -2.1259   -2.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665   -3.1124   -1.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528   -3.7025   -0.6244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -3.9305   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -2.5398   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.7072    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621   -0.2476    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856    0.3346    0.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174    0.1757    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -0.5731    1.9452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3259    0.8413    0.8271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1263    0.4737    1.9025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0343    0.3931   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3808    1.0857   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195   -1.0825   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2032    2.3522    0.8877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4640    2.9243   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    2.7376    2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -2.5260    0.1212 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9444    3.3736    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144    3.7278   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996    4.0698    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515    1.8748    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2954    1.7590    1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625    1.7916   -0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8008    0.2869    0.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128   -2.7082   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -1.1246   -2.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624   -2.5239   -2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9601   -3.8818   -2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196   -2.5513   -2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200   -4.2691    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7765   -4.6107   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7591   -2.3300   -0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974    0.2241   -0.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301    0.0620    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7999    1.1720    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411    0.6146   -1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9489    0.9815    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9392    0.5754   -1.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2595    2.1403   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9588   -1.5476    0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7695   -1.5871   -1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3899   -1.3322   -0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2499    2.7495    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687    3.5159    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173    2.1177   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0924    3.6666   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202    3.6728    2.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8569   -2.7529    1.1603 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 24 26  1  0
 14 27  1  0
 27  8  1  0
 27 11  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  1
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  1
M  END


  Mrv1572004201615532D          

 31 32  0  0  1  0            999 V2000
    3.8585   -2.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127   -0.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626   -1.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019   -2.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0258   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827   -2.3068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9007   -0.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -1.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -2.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4527    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -1.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -1.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -0.5436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -0.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -1.7698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -1.7547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554   -0.1709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    1.1524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  2  0  0  0  0
 14  5  1  0  0  0  0
 15  7  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  6  0  0  0
 21  9  1  0  0  0  0
 21 10  1  0  0  0  0
 21 17  1  0  0  0  0
 14 22  1  1  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
 20 25  1  6  0  0  0
 26 11  1  0  0  0  0
 26 19  1  0  0  0  0
 16 27  1  1  0  0  0
 27 18  1  0  0  0  0
 28  6  1  0  0  0  0
 14 29  1  1  0  0  0
 16 30  1  6  0  0  0
 17 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137587

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C(\C)C(=O)O[C@]1([H])CCN2CC=C(COC(=O)[C@](O)(C(C)C)[C@]([H])(C)O)[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H31NO6/c1-6-13(4)18(23)27-16-8-10-21-9-7-15(17(16)21)11-26-19(24)20(25,12(2)3)14(5)22/h6-7,12,14,16-17,22,25H,8-11H2,1-5H3/b13-6+/t14-,16+,17+,20-/m0/s1

> <INCHI_KEY>
MVWPTZQHBOWRTF-SMLWLWDZSA-N

> <FORMULA>
C20H31NO6

> <MOLECULAR_WEIGHT>
381.469

> <EXACT_MASS>
381.215137722

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.074833292300596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7aR)-7-({[(2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
1.921822241

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.800899080102127

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.342569223627944

> <JCHEM_PKA_STRONGEST_BASIC>
7.136044368210528

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
101.77229999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
symphytine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-16         0                                  
HETATM    1  C   UNK     0       7.203  -5.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.379  -0.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -0.263   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.264  -2.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.190  -4.782   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.727  -3.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.204   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.370   3.262   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.299   3.262   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.894  -0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.915  -1.293   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.757  -2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.274  -4.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.834   1.246   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.281  -1.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.088  -2.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.595  -2.800   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.834   2.786   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -2.419  -5.336   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.312   0.130   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.942  -3.624   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.101  -3.120   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.388  -1.015   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.775  -0.695   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       5.220  -3.304   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.130  -3.276   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.210  -0.319   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.080   2.151   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6    1   13   28                                                  
CONECT    7    9   15                                                       
CONECT    8   10   16                                                       
CONECT    9    7   21                                                       
CONECT   10    8   21                                                       
CONECT   11   15   26                                                       
CONECT   12    2    3   20                                                  
CONECT   13    4    6   18                                                  
CONECT   14    5   20   22   29                                             
CONECT   15    7   11   17                                                  
CONECT   16    8   17   27   30                                             
CONECT   17   15   16   21   31                                             
CONECT   18   13   23   27                                                  
CONECT   19   20   24   26                                                  
CONECT   20   12   14   19   25                                             
CONECT   21    9   10   17                                                  
CONECT   22   14                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   11   19                                                       
CONECT   27   16   18                                                       
CONECT   28    6                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
7-Tiglyl-9-(-)-viridiflorylretronecine	ChEBI
7-Tiglylretronecine viridiflorate	ChEBI
7-Tiglylretronecine viridifloric acid	Generator
[(7R,8R)-7-[(e)-2-Methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoic acid	Generator
7-Tiglylretronecine viridiflate	Generator
7-Tiglylretronecine viridiflic acid	Generator
Symphytine	MeSH

Chemical Formula

C₂₀H₃₁NO₆

Average Mass

381.4690 Da

Monoisotopic Mass

381.21514 Da

IUPAC Name

(1R,7aR)-7-({[(2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2E)-2-methylbut-2-enoate

Traditional Name

symphytine

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(\C)C(=O)O[C@]1([H])CCN2CC=C(COC(=O)[C@](O)(C(C)C)[C@]([H])(C)O)[C@]12[H]

InChI Identifier

InChI=1S/C20H31NO6/c1-6-13(4)18(23)27-16-8-10-21-9-7-15(17(16)21)11-26-19(24)20(25,12(2)3)14(5)22/h6-7,12,14,16-17,22,25H,8-11H2,1-5H3/b13-6+/t14-,16+,17+,20-/m0/s1

InChI Key

MVWPTZQHBOWRTF-SMLWLWDZSA-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
Myosotis scorpioides	LOTUS Database	35616633
Pulmonaria obscura	LOTUS Database	35616633
Symphytum officinale	LOTUS Database	35616633
Symphytum uplandicum	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

Alkaloid or derivatives
Pyrrolizine
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Hydroxy acid
Fatty acyl
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Alcohol
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyrrolizines (CHEBI:9375 )
but-2-enoate ester (CHEBI:9375 )
Pyrrolizidine alkaloids (C10409 )

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	2.09	ALOGPS
logP	1.92	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	7.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	101.77 m³·mol⁻¹	ChemAxon
Polarizability	41.07 Å³	ChemAxon
Number of Rings	2	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

C00002123

Chemspider ID

Not Available

KEGG Compound ID

C10409

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281754

PDB ID

Not Available

ChEBI ID

9375

Good Scents ID

Not Available

References

General References

Kim NC, Oberlies NH, Brine DR, Handy RW, Wani MC, Wall ME: Isolation of symlandine from the roots of common comfrey (Symphytum officinale) using countercurrent chromatography. J Nat Prod. 2001 Feb;64(2):251-3. doi: 10.1021/np0004653. [PubMed:11430014 ]
Oberlies NH, Kim NC, Brine DR, Collins BJ, Handy RW, Sparacino CM, Wani MC, Wall ME: Analysis of herbal teas made from the leaves of comfrey (Symphytum officinale): reduction of N-oxides results in order of magnitude increases in the measurable concentration of pyrrolizidine alkaloids. Public Health Nutr. 2004 Oct;7(7):919-24. doi: 10.1079/phn2004624. [PubMed:15482618 ]
Wagner H, Neidhardt U, Tittel G: [II1: TLC and HPLC-Analysis of Pyrrolizidine-N-oxid Alkaloids of Symphyti Radix]. Planta Med. 1981 Mar;41(3):232-9. doi: 10.1055/s-2007-971708. [PubMed:17401847 ]
Hirono I, Haga M, Fujii M, Matsuura S, Matsubara N, Nakayama M, Furuya T, Hikichi M, Takanashi H, Uchida E, Hosaka S, Ueno I: Induction of hepatic tumors in rats by senkirkine and symphytine. J Natl Cancer Inst. 1979 Aug;63(2):469-72. [PubMed:287835 ]
Authors unspecified: Symphytine. IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Jul;31:239-45. [PubMed:6579012 ]

Showing NP-Card for Symphytine (NP0137587)

MOL for NP0137587 (Symphytine)

3D MOL for NP0137587 (Symphytine)

3D SDF for NP0137587 (Symphytine)

3D-SDF for NP0137587 (Symphytine)

PDB for NP0137587 (Symphytine)

3D PDB for NP0137587 (Symphytine)

SMILES for NP0137587 (Symphytine)

INCHI for NP0137587 (Symphytine)

Structure for NP0137587 (Symphytine)

3D Structure for NP0137587 (Symphytine)