NP-MRD: Showing NP-Card for 16,19-epoxy-Delta14-vincanol (NP0041744)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 23:35:11 UTC

Updated at

2021-06-30 00:16:26 UTC

NP-MRD ID

NP0041744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16,19-epoxy-Delta14-vincanol

Provided By

JEOL Database JEOL Logo

Description

(3S,14S,16S,20R)-14,20-Epoxy-14,15-dihydro-17,18-didehydroeburnamenine belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. 16,19-epoxy-Delta14-vincanol is found in Melodinus yunnanensis. 16,19-epoxy-Delta14-vincanol was first documented in 2012 (Cai, X.-H., et al.). Based on a literature review very few articles have been published on (3S,14S,16S,20R)-14,20-Epoxy-14,15-dihydro-17,18-didehydroeburnamenine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101353D          

 42 47  0  0  0  0            999 V2000
   -3.2350    1.8208    1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160    0.7996    1.6956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3293    0.1938    0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    0.4404   -0.4049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5266    1.6978    0.1958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6597    1.3621    1.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    2.5719    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    2.6138    3.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5074    3.6442 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6781    0.6066    2.4921 N   0  0  1  0  0  0  0  0  0  0  0  0
    2.5208   -0.5859    2.8060 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7493   -1.5687    1.6107 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5846   -1.5702    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.7433    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.6853   -0.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1811   -1.6316   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0080   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.9810   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -3.5471   -2.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -3.1596   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -2.2004   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202    0.1752    2.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2104    1.3362    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036    2.2716    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    2.6146    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466    0.0141    2.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121    0.5344   -1.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063    1.8705   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    2.5826   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    3.4360    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    3.4961    4.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.9649    3.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.9673    4.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1490    3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -0.2590    3.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -1.2428    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.5774    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -1.5675   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -3.2952   -4.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -4.2953   -3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640   -3.5997   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -0.3984    2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 10 22  1  0  0  0  0
 13 21  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 10  9  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 22 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  2  0  0  0  0
 17 16  1  0  0  0  0
 13 14  2  0  0  0  0
 10 11  1  0  0  0  0
 22  6  1  0  0  0  0
 15  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 12 11  1  0  0  0  0
  6  2  1  0  0  0  0
 16 21  2  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 15 14  1  0  0  0  0
  2  1  1  0  0  0  0
 21 20  1  0  0  0  0
 22 42  1  1  0  0  0
 20 41  1  0  0  0  0
 19 40  1  0  0  0  0
 18 39  1  0  0  0  0
 17 38  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
  4 27  1  6  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  2 26  1  1  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END

     RDKit          3D

 42 47  0  0  0  0  0  0  0  0999 V2000
   -3.2350    1.8208    1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160    0.7996    1.6956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3293    0.1938    0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    0.4404   -0.4049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5266    1.6978    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597    1.3621    1.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    2.5719    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    2.6138    3.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5074    3.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    0.6066    2.4921 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -0.5859    2.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7493   -1.5687    1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846   -1.5702    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.7433    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.6853   -0.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1811   -1.6316   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0080   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.9810   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -3.5471   -2.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -3.1596   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -2.2004   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202    0.1752    2.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2104    1.3362    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036    2.2716    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    2.6146    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466    0.0141    2.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121    0.5344   -1.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063    1.8705   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    2.5826   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    3.4360    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    3.4961    4.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.9649    3.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.9673    4.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1490    3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -0.2590    3.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -1.2428    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.5774    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -1.5675   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -3.2952   -4.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -4.2953   -3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640   -3.5997   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -0.3984    2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 10 22  1  0
 13 21  1  0
 20 19  2  0
 19 18  1  0
 10  9  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
 22 14  1  0
 16 15  1  0
 18 17  2  0
 17 16  1  0
 13 14  2  0
 10 11  1  0
 22  6  1  0
 15  4  1  0
  4  5  1  0
  5  6  1  0
 12 11  1  0
  6  2  1  0
 16 21  2  0
  4  3  1  0
  3  2  1  0
 15 14  1  0
  2  1  1  0
 21 20  1  0
 22 42  1  1
 20 41  1  0
 19 40  1  0
 18 39  1  0
 17 38  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
  4 27  1  6
  5 28  1  0
  5 29  1  0
  2 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652306212101353D          

 42 47  0  0  0  0            999 V2000
   -3.2350    1.8208    1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160    0.7996    1.6956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3293    0.1938    0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    0.4404   -0.4049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5266    1.6978    0.1958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6597    1.3621    1.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    2.5719    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    2.6138    3.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5074    3.6442 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6781    0.6066    2.4921 N   0  0  1  0  0  0  0  0  0  0  0  0
    2.5208   -0.5859    2.8060 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7493   -1.5687    1.6107 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5846   -1.5702    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.7433    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.6853   -0.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1811   -1.6316   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0080   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.9810   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -3.5471   -2.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -3.1596   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -2.2004   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202    0.1752    2.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2104    1.3362    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036    2.2716    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    2.6146    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466    0.0141    2.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121    0.5344   -1.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063    1.8705   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    2.5826   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    3.4360    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    3.4961    4.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.9649    3.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.9673    4.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1490    3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -0.2590    3.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -1.2428    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.5774    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -1.5675   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -3.2952   -4.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -4.2953   -3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640   -3.5997   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -0.3984    2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 10 22  1  0  0  0  0
 13 21  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 10  9  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 22 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  2  0  0  0  0
 17 16  1  0  0  0  0
 13 14  2  0  0  0  0
 10 11  1  0  0  0  0
 22  6  1  0  0  0  0
 15  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 12 11  1  0  0  0  0
  6  2  1  0  0  0  0
 16 21  2  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 15 14  1  0  0  0  0
  2  1  1  0  0  0  0
 21 20  1  0  0  0  0
 22 42  1  1  0  0  0
 20 41  1  0  0  0  0
 19 40  1  0  0  0  0
 18 39  1  0  0  0  0
 17 38  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
  4 27  1  6  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  2 26  1  1  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(C([H])=C1[H])C1=C3N2[C@@]2([H])O[C@]([H])(C([H])([H])[H])[C@]4(C([H])=C([H])C([H])([H])N(C([H])([H])C1([H])[H])[C@]34[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O/c1-12-19-8-4-9-20-10-7-14-13-5-2-3-6-15(13)21(16(11-19)22-12)17(14)18(19)20/h2-6,8,12,16,18H,7,9-11H2,1H3/t12-,16+,18-,19+/m1/s1

> <INCHI_KEY>
FTSPQTZEHUCKSF-QUSXHRHCSA-N

> <FORMULA>
C19H20N2O

> <MOLECULAR_WEIGHT>
292.382

> <EXACT_MASS>
292.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.362956293924405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15S,16R,18S,20S)-16-methyl-17-oxa-1,11-diazahexacyclo[9.7.2.1^{15,18}.0^{2,7}.0^{8,19}.0^{15,20}]henicosa-2(7),3,5,8(19),13-pentaene

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.875112102666666

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.719959837302389

> <JCHEM_POLAR_SURFACE_AREA>
17.4

> <JCHEM_REFRACTIVITY>
87.50760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S,16R,18S,20S)-16-methyl-17-oxa-1,11-diazahexacyclo[9.7.2.1^{15,18}.0^{2,7}.0^{8,19}.0^{15,20}]henicosa-2(7),3,5,8(19),13-pentaene

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 42 47  0  0  0  0  0  0  0  0999 V2000
   -3.2350    1.8208    1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160    0.7996    1.6956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3293    0.1938    0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    0.4404   -0.4049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5266    1.6978    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597    1.3621    1.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    2.5719    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    2.6138    3.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5074    3.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    0.6066    2.4921 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -0.5859    2.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7493   -1.5687    1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846   -1.5702    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.7433    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.6853   -0.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1811   -1.6316   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0080   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.9810   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -3.5471   -2.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -3.1596   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -2.2004   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202    0.1752    2.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2104    1.3362    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036    2.2716    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    2.6146    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466    0.0141    2.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121    0.5344   -1.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063    1.8705   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    2.5826   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    3.4360    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    3.4961    4.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.9649    3.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.9673    4.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1490    3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -0.2590    3.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -1.2428    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.5774    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -1.5675   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -3.2952   -4.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -4.2953   -3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640   -3.5997   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -0.3984    2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 10 22  1  0
 13 21  1  0
 20 19  2  0
 19 18  1  0
 10  9  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
 22 14  1  0
 16 15  1  0
 18 17  2  0
 17 16  1  0
 13 14  2  0
 10 11  1  0
 22  6  1  0
 15  4  1  0
  4  5  1  0
  5  6  1  0
 12 11  1  0
  6  2  1  0
 16 21  2  0
  4  3  1  0
  3  2  1  0
 15 14  1  0
  2  1  1  0
 21 20  1  0
 22 42  1  1
 20 41  1  0
 19 40  1  0
 18 39  1  0
 17 38  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
  4 27  1  6
  5 28  1  0
  5 29  1  0
  2 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.235   1.821   1.886  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.116   0.800   1.696  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.329   0.194   0.392  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.156   0.440  -0.405  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.527   1.698   0.196  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.660   1.362   1.692  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.412   2.572   2.565  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.595   2.614   3.452  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.596   1.507   3.644  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.678   0.607   2.492  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.521  -0.586   2.806  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.749  -1.569   1.611  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.585  -1.570   0.683  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.517  -0.743   0.919  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.247  -0.685  -0.212  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.181  -1.632  -1.112  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.318  -2.008  -2.367  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.383  -2.981  -3.086  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.550  -3.547  -2.579  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.048  -3.160  -1.331  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.350  -2.200  -0.571  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.320   0.175   2.080  0.00  0.00           C+0
HETATM   23  H   UNK     0      -4.210   1.336   1.764  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.204   2.272   2.882  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.190   2.615   1.133  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.247   0.014   2.449  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.412   0.534  -1.463  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.506   1.871  -0.127  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.120   2.583  -0.066  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.063   3.436   2.465  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.724   3.496   4.074  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.581   1.965   3.798  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.337   0.967   4.564  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.062  -1.149   3.631  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.506  -0.259   3.162  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.636  -1.243   1.052  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.943  -2.577   1.991  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.223  -1.567  -2.773  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.013  -3.295  -4.059  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.084  -4.295  -3.160  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.964  -3.600  -0.948  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.127  -0.398   2.906  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    6    3    1   26                                             
CONECT    3    4    2                                                       
CONECT    4   15    5    3   27                                             
CONECT    5    4    6   28   29                                             
CONECT    6    7   22    5    2                                             
CONECT    7    6    8   30                                                  
CONECT    8    7    9   31                                                  
CONECT    9   10    8   32   33                                             
CONECT   10   22    9   11                                                  
CONECT   11   10   12   34   35                                             
CONECT   12   13   11   36   37                                             
CONECT   13   12   21   14                                                  
CONECT   14   22   13   15                                                  
CONECT   15   16    4   14                                                  
CONECT   16   15   17   21                                                  
CONECT   17   18   16   38                                                  
CONECT   18   19   17   39                                                  
CONECT   19   20   18   40                                                  
CONECT   20   19   21   41                                                  
CONECT   21   13   16   20                                                  
CONECT   22   10   14    6   42                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   22                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

RDKit          3D

42 47  0  0  0  0  0  0  0  0999 V2000
   -3.2350    1.8208    1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160    0.7996    1.6956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3293    0.1938    0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    0.4404   -0.4049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5266    1.6978    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597    1.3621    1.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    2.5719    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    2.6138    3.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5074    3.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    0.6066    2.4921 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -0.5859    2.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7493   -1.5687    1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846   -1.5702    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.7433    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.6853   -0.2115 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1811   -1.6316   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0080   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.9810   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -3.5471   -2.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -3.1596   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -2.2004   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202    0.1752    2.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2104    1.3362    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036    2.2716    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    2.6146    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466    0.0141    2.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121    0.5344   -1.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063    1.8705   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    2.5826   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    3.4360    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    3.4961    4.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.9649    3.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.9673    4.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1490    3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -0.2590    3.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -1.2428    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.5774    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -1.5675   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -3.2952   -4.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -4.2953   -3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640   -3.5997   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -0.3984    2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 10 22  1  0
 13 21  1  0
 20 19  2  0
 19 18  1  0
 10  9  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
 22 14  1  0
 16 15  1  0
 18 17  2  0
 17 16  1  0
 13 14  2  0
 10 11  1  0
 22  6  1  0
 15  4  1  0
  4  5  1  0
  5  6  1  0
 12 11  1  0
  6  2  1  0
 16 21  2  0
  4  3  1  0
  3  2  1  0
 15 14  1  0
  2  1  1  0
 21 20  1  0
 22 42  1  1
 20 41  1  0
 19 40  1  0
 18 39  1  0
 17 38  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
  4 27  1  6
  5 28  1  0
  5 29  1  0
  2 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀N₂O

Average Mass

292.3820 Da

Monoisotopic Mass

292.15756 Da

IUPAC Name

(15S,16R,18S,20S)-16-methyl-17-oxa-1,11-diazahexacyclo[9.7.2.1^{15,18}.0^{2,7}.0^{8,19}.0^{15,20}]henicosa-2(7),3,5,8(19),13-pentaene

Traditional Name

(15S,16R,18S,20S)-16-methyl-17-oxa-1,11-diazahexacyclo[9.7.2.1^{15,18}.0^{2,7}.0^{8,19}.0^{15,20}]henicosa-2(7),3,5,8(19),13-pentaene

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(C([H])=C1[H])C1=C3N2[C@@]2([H])O[C@]([H])(C([H])([H])[H])[C@]4(C([H])=C([H])C([H])([H])N(C([H])([H])C1([H])[H])[C@]34[H])C2([H])[H]

InChI Identifier

InChI=1S/C19H20N2O/c1-12-19-8-4-9-20-10-7-14-13-5-2-3-6-15(13)21(16(11-19)22-12)17(14)18(19)20/h2-6,8,12,16,18H,7,9-11H2,1H3/t12-,16+,18-,19+/m1/s1

InChI Key

FTSPQTZEHUCKSF-QUSXHRHCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melodinus yunnanensis	JEOL database	Cai, X.-H., et al, Phytochem. 83, 116 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Meta-oxazepine
Aralkylamine
Benzenoid
Pyrrole
Oxolane
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.95	ALOGPS
logP	2.88	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	6.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.4 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.51 m³·mol⁻¹	ChemAxon
Polarizability	33.36 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

71501404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cai, X.-H., et al. (2012). Cai, X.-H., et al, Phytochem. 83, 116 (2012). Phytochem..

Showing NP-Card for 16,19-epoxy-Delta14-vincanol (NP0041744)

MOL for NP0041744 (16,19-epoxy-Delta14-vincanol)

3D MOL for NP0041744 (16,19-epoxy-Delta14-vincanol)

3D SDF for NP0041744 (16,19-epoxy-Delta14-vincanol)

3D-SDF for NP0041744 (16,19-epoxy-Delta14-vincanol)

PDB for NP0041744 (16,19-epoxy-Delta14-vincanol)

3D PDB for NP0041744 (16,19-epoxy-Delta14-vincanol)

SMILES for NP0041744 (16,19-epoxy-Delta14-vincanol)

INCHI for NP0041744 (16,19-epoxy-Delta14-vincanol)

Structure for NP0041744 (16,19-epoxy-Delta14-vincanol)

3D Structure for NP0041744 (16,19-epoxy-Delta14-vincanol)