NP-MRD: Showing NP-Card for (1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate (NP0217991)

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Record Information

Version

2.0

Created at

2022-09-05 18:30:29 UTC

Updated at

2022-09-05 18:30:29 UTC

NP-MRD ID

NP0217991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate

Description

(1S,2R,4R,5S,9S,10S,12R)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-4-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. Based on a literature review very few articles have been published on (1S,2R,4R,5S,9S,10S,12R)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-4-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052220302D          

 28 31  0  0  1  0            999 V2000
    9.6992   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6992    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9847    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9847    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2703    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2703   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5558    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1269    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8290    1.4084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6655    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8290   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5558   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2773   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2773   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  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  1  6  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  6  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -5.0405    0.7272   -2.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1125    1.2517   -1.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0897    1.1916   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1934    1.7343    0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588    0.5801    0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9161    0.5113    1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8628    0.0351   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7748   -0.5548    0.5756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4982    0.2380    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4053   -0.5413    1.0677 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8707    0.2046    1.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8431   -0.7535    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -1.7197    0.7956 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1457   -2.3211    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346   -1.7448    0.3022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2797   -2.3858   -0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -3.2483   -1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144   -2.0067    0.2790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8209   -2.8162    1.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971   -0.8605   -0.1726 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1005    0.0034    0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0584    0.5381   -0.5095 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5156    1.7938   -0.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973    1.8089    0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3714    0.5065   -1.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096    0.8125   -1.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805   -0.0084   -0.8505 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3862    0.8326   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711    1.2369   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9412   -0.3580   -2.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3413    0.8820   -3.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9965    1.7270   -1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3675    1.0486    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9516    2.7423    1.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1036    1.8639    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104   -0.4732    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.3205   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    1.2187    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737   -0.8380    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996    1.0229    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6721   -0.2718    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.3576    2.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900   -2.4882    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0858   -3.4079    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3884   -2.3714   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4310   -2.2987   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -2.5689    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5839   -1.5136   -0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    0.9030    0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -0.5619    1.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9160   -0.1691   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1931    1.1016    0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561    2.8275    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4614    1.6160   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8488    1.2928   -2.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5829   -0.4584   -2.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    1.9051   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    0.6617   -2.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9448    1.7885    0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078    1.1691   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
  8 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  2  0
 13 20  1  0
 20 21  1  0
 21 22  1  0
 20 27  1  0
 10 11  1  0
 16 15  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 22 51  1  6
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 28 59  1  0
 28 60  1  0
 11 40  1  1
 12 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 14 45  1  0
 10 39  1  1
  9 37  1  0
  9 38  1  0
  8 36  1  1
  4 33  1  0
  4 34  1  0
  4 35  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 18 46  1  6
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
M  END


  Mrv1652309052220302D          

 28 31  0  0  1  0            999 V2000
    9.6992   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6992    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9847    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9847    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2703    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2703   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5558    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1269    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8290    1.4084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6655    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8290   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5558   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2773   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2773   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  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  1  6  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  6  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1CCN2C[C@@H]3C[C@@H](CN4[C@@H]3C[C@@H](OC(=O)C(\C)=C/C)[C@H](O)C4=O)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H32N2O5/c1-4-12(2)21(26)28-18-9-17-13-7-14(11-23(17)20(25)19(18)24)16-8-15(27-3)5-6-22(16)10-13/h4,13-19,24H,5-11H2,1-3H3/b12-4-/t13-,14-,15+,16-,17+,18+,19-/m0/s1

> <INCHI_KEY>
YVQJCCQBPAKQKB-HHBUVEIYSA-N

> <FORMULA>
C21H32N2O5

> <MOLECULAR_WEIGHT>
392.496

> <EXACT_MASS>
392.231122138

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.858734255867276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5S,9S,10S,12R)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
0.38092097766666605

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.399928014899828

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.168781894599128

> <JCHEM_PKA_STRONGEST_BASIC>
9.374350668131239

> <JCHEM_POLAR_SURFACE_AREA>
79.31

> <JCHEM_REFRACTIVITY>
104.42189999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5S,9S,10S,12R)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      18.105  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.105   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.772   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.772   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.438   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      15.438  -0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.104   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.770   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.437   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.103   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.014   2.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.709   0.577   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.474  -1.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.014  -1.089   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      10.103  -0.000   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      11.437  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.437  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.770  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.104  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.718   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.384  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.384  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.718   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.385   1.540   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       7.474   2.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    8   19                                                  
CONECT   19   18                                                            
CONECT   20   13   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27   11                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4R,5S,9S,10S,12R)-5-Hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0,.0,]heptadecan-4-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₁H₃₂N₂O₅

Average Mass

392.4960 Da

Monoisotopic Mass

392.23112 Da

IUPAC Name

(1S,2R,4R,5S,9S,10S,12R)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1S,2R,4R,5S,9S,10S,12R)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1CCN2C[C@@H]3C[C@@H](CN4[C@@H]3C[C@@H](OC(=O)C(\C)=C/C)[C@H](O)C4=O)[C@@H]2C1

InChI Identifier

InChI=1S/C21H32N2O5/c1-4-12(2)21(26)28-18-9-17-13-7-14(11-23(17)20(25)19(18)24)16-8-15(27-3)5-6-22(16)10-13/h4,13-19,24H,5-11H2,1-3H3/b12-4-/t13-,14-,15+,16-,17+,18+,19-/m0/s1

InChI Key

YVQJCCQBPAKQKB-HHBUVEIYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidinone
Quinolizidine
Delta-lactam
Fatty acid ester
Piperidinone
Fatty acyl
Piperidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Lactam
Carboxylic acid ester
Carboxamide group
Amino acid or derivatives
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Alcohol
Organooxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
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	0.38	ChemAxon
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	9.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	79.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.42 m³·mol⁻¹	ChemAxon
Polarizability	42.86 Å³	ChemAxon
Number of Rings	4	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

10201790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21586424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate (NP0217991)

MOL for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

PDB for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

Structure for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0217991 ((1s,2r,4r,5s,9s,10s,12r)-5-hydroxy-12-methoxy-6-oxo-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-4-yl (2z)-2-methylbut-2-enoate)