NP-MRD: Showing NP-Card for 3'-Acetylheliosupine (NP0068261)

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Record Information

Version

2.0

Created at

2022-04-28 13:23:43 UTC

Updated at

2022-04-28 13:23:43 UTC

NP-MRD ID

NP0068261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-Acetylheliosupine

Description

Acetylheliosupine 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. 3'-Acetylheliosupine is found in Cynoglossum officinale . Based on a literature review very few articles have been published on Acetylheliosupine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215232D          

 31 32  0  0  1  0            999 V2000
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1832   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.8933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902   -1.8495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1617   -1.0425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9463   -0.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1178    0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9025    0.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5047    0.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486   -0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8186   -2.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -2.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -2.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -2.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -3.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -3.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590   -1.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  1  0  0  0
 13 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
 16 18  1  0  0  0  0
 14 19  1  6  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 24  1  1  0  0  0
  3 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
    5.9119    0.6862   -1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690   -0.7265   -1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3400   -1.7099   -1.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5589   -3.0981   -1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3362   -1.4441   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120   -2.3685    0.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854   -0.1723    0.1801 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993    0.0612    1.1589 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8406    0.6356    2.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0554    1.9153    2.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986    1.5636    2.2114 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8801    2.6084    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466    1.7683    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8569    0.8870    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4760   -0.1226   -0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8397   -0.1954   -1.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591   -0.4641   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483   -0.6803    0.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -0.5252   -0.9494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1765   -0.1274   -2.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2921    0.3887   -0.2894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6584    0.3288   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515    1.7382   -0.2347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885    2.4090    0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222    3.8384    1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1342    1.7793    1.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -1.9799   -0.9817 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7920   -2.3583   -1.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0073   -2.6174    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550   -2.6957   -1.5143 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    1.1669    0.8565 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9037    1.0947   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6341    1.3233   -1.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    0.7400   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8255   -0.9640   -2.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5692   -3.0502   -2.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104   -3.7950   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5590   -3.4790   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.8981    1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8823    0.8505    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666   -0.0496    3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    2.0616    3.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    2.7648    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    2.9943    2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812    3.3950    1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    1.9228    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188   -1.0892   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743    0.1263   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -0.8689   -2.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820    0.0893    0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1583    1.3398   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6595    0.0189   -1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3110   -0.3273   -0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1589    4.4808    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4951    3.9617    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263    4.1872    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6638   -3.4740   -2.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6915   -1.8825   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7589   -2.3019   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3332   -1.8942    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -3.0661    0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7304   -3.4593    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1276   -3.2337   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    1.9927    0.3556 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
  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  6
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 19 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  6
 14 31  1  0
 31  8  1  0
 31 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 15 47  1  0
 15 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 22 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 31 64  1  6
M  END


  Mrv1652304282215232D          

 31 32  0  0  1  0            999 V2000
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1832   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.8933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902   -1.8495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1617   -1.0425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9463   -0.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1178    0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9025    0.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5047    0.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486   -0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8186   -2.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -2.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -2.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -2.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -3.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -3.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590   -1.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  1  0  0  0
 13 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
 16 18  1  0  0  0  0
 14 19  1  6  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 24  1  1  0  0  0
  3 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068261

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO8/c1-7-13(2)19(25)31-17-9-11-23-10-8-16(18(17)23)12-29-20(26)22(28,21(5,6)27)14(3)30-15(4)24/h7-8,14,17-18,27-28H,9-12H2,1-6H3/b13-7-/t14-,17-,18+,22+/m0/s1

> <INCHI_KEY>
LHYJPODIMQKZHJ-ZEQSJKFYSA-N

> <FORMULA>
C22H33NO8

> <MOLECULAR_WEIGHT>
439.505

> <EXACT_MASS>
439.220617027

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
45.08696824865797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7aR)-7-({[(2S)-2-[(1S)-1-(acetyloxy)ethyl]-2,3-dihydroxy-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.1256941563333323

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.547071405333671

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.51513849717482

> <JCHEM_PKA_STRONGEST_BASIC>
8.134252979132894

> <JCHEM_POLAR_SURFACE_AREA>
122.6

> <JCHEM_REFRACTIVITY>
112.5289

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7aR)-7-({[(2S)-2-[(1S)-1-(acetyloxy)ethyl]-2,3-dihydroxy-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

> <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      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.465  -0.476   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.911  -4.277   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.942  -3.132   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.466  -1.668   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.448  -3.452   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.768  -1.946   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.233  -1.470   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.553   0.036   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.018   0.512   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.409   1.067   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.624  -0.916   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.128  -4.959   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.808  -6.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.622  -4.638   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.634  -5.279   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.955  -3.773   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.476  -3.956   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.555  -5.101   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.079  -6.565   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.061  -4.781   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.091  -5.925   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.615  -7.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.537  -3.316   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20   24                                             
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20   13   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   13                                                            
CONECT   25    3   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₈

Average Mass

439.5050 Da

Monoisotopic Mass

439.22062 Da

IUPAC Name

(1S,7aR)-7-({[(2S)-2-[(1S)-1-(acetyloxy)ethyl]-2,3-dihydroxy-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1S,7aR)-7-({[(2S)-2-[(1S)-1-(acetyloxy)ethyl]-2,3-dihydroxy-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H33NO8/c1-7-13(2)19(25)31-17-9-11-23-10-8-16(18(17)23)12-29-20(26)22(28,21(5,6)27)14(3)30-15(4)24/h7-8,14,17-18,27-28H,9-12H2,1-6H3/b13-7-/t14-,17-,18+,22+/m0/s1

InChI Key

LHYJPODIMQKZHJ-ZEQSJKFYSA-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
Cynoglossum officinale	Plant	KNApSAcK

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
Tricarboxylic acid or derivatives
Pyrrolizine
Fatty acid ester
Fatty acyl
N-alkylpyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Pyrroline
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
1,2-diol
Azacycle
Organoheterocyclic compound
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	1.49	ALOGPS
logP	1.13	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.52	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	112.53 m³·mol⁻¹	ChemAxon
Polarizability	45.09 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

C00026158

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

156593815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3'-Acetylheliosupine (NP0068261)

MOL for NP0068261 (3'-Acetylheliosupine)

3D MOL for NP0068261 (3'-Acetylheliosupine)

3D SDF for NP0068261 (3'-Acetylheliosupine)

3D-SDF for NP0068261 (3'-Acetylheliosupine)

PDB for NP0068261 (3'-Acetylheliosupine)

3D PDB for NP0068261 (3'-Acetylheliosupine)

SMILES for NP0068261 (3'-Acetylheliosupine)

INCHI for NP0068261 (3'-Acetylheliosupine)

Structure for NP0068261 (3'-Acetylheliosupine)

3D Structure for NP0068261 (3'-Acetylheliosupine)