NP-MRD: Showing NP-Card for (1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one (NP0317444)

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Record Information

Version

2.0

Created at

2022-09-11 17:20:22 UTC

Updated at

2022-09-11 17:20:23 UTC

NP-MRD ID

NP0317444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

Description

Humantenidine belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one is found in Gelsemium sempervirens. (1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one was first documented in 2014 (PMID: 24375943). Based on a literature review very few articles have been published on Humantenidine (PMID: 29234422).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112219202D          

 25 29  0  0  1  0            999 V2000
   -1.6257    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718    0.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625    0.9607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198    1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119    0.7300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4939    1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8780    2.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.7266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317    2.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    0.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1673    0.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2772   -0.1100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2965   -0.9626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031   -1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4236   -0.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4506    0.7989    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -4.4820   -0.6076    1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061    0.2357    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017    0.4092   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661    1.5870   -0.4542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3090    1.4104   -0.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4370    1.3742    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936    0.3109    0.2729 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9929    0.0333    1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -0.1665    2.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    0.0072    1.7269 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1986   -0.3896    2.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8508   -1.5576    2.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8816    0.4780    0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1869    0.7570    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4758    1.3284   -1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4284    1.6386   -2.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    1.3586   -1.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    0.7812   -0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -1.0158   -0.2861 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4628   -1.0692   -1.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507   -0.4996   -2.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379    0.2368   -1.8331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3421   -0.6367   -0.8629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3475   -1.2892    0.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6034   -1.0995    1.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5321   -0.5585    2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -1.6612    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692   -0.1501    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2611   -0.2449   -0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9562    1.2287    0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587    2.3481   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9853    1.3525    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154    2.3614    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9556   -1.4893    2.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -2.4515    2.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7472   -1.7451    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056    0.5079    0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4803    1.5376   -1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    2.0903   -2.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572    1.6484   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715   -1.8516    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302    0.0502   -3.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335   -1.4072   -2.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835    0.5162   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141   -1.3532   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -2.4124   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507   -1.9317    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  7  8  1  1
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 23  3  1  0
 18 13  1  0
 22  5  1  0
 18  7  1  0
 24 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  5 31  1  6
  6 32  1  0
  6 33  1  0
 19 41  1  1
 21 42  1  0
 21 43  1  0
 22 44  1  6
 23 45  1  6
 24 46  1  1
 25 47  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
M  END


  Mrv1652309112219202D          

 25 29  0  0  1  0            999 V2000
   -1.6257    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718    0.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625    0.9607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198    1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119    0.7300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4939    1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8780    2.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.7266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317    2.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    0.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1673    0.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2772   -0.1100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2965   -0.9626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031   -1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4236   -0.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4506    0.7989    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0317444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=NC2C[C@]3([C@@H]4OCC2C1[C@@H]4O)C(=O)N(OC)C1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O4/c1-3-12-15-10-9-25-17(16(15)22)19(8-13(10)20-12)11-6-4-5-7-14(11)21(24-2)18(19)23/h4-7,10,13,15-17,22H,3,8-9H2,1-2H3/t10?,13?,15?,16-,17+,19-/m0/s1

> <INCHI_KEY>
FLDAHLDTMBMPJD-MUNBIJQLSA-N

> <FORMULA>
C19H22N2O4

> <MOLECULAR_WEIGHT>
342.395

> <EXACT_MASS>
342.157957196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.52822293100648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3S,11'S)-6'-ethyl-11'-hydroxy-1-methoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0^{4,8}]undecan]-5'-en-2-one

> <JCHEM_LOGP>
1.1036178216666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.77262942943365

> <JCHEM_PKA_STRONGEST_BASIC>
5.9563101612299345

> <JCHEM_POLAR_SURFACE_AREA>
71.36000000000001

> <JCHEM_REFRACTIVITY>
90.02260000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3S,11'S)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0^{4,8}]undecan]-5'-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.035   1.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.017   0.304   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.507   0.607   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.490   1.793   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.797   0.847   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.024   1.920   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.502   1.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.655   2.895   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.506   3.920   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       6.160   3.223   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       6.779   4.633   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.310   4.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.937   1.893   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.445   1.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.928   0.119   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.904  -1.031   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.396  -0.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.912   0.743   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.251  -0.205   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.287  -1.797   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.806  -2.340   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.961  -0.986   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.880  -0.107   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.657  -0.048   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.708   1.491   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18   19                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13    7                                                  
CONECT   19    7   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    5   23                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Humantendine	MeSH

Chemical Formula

C₁₉H₂₂N₂O₄

Average Mass

342.3950 Da

Monoisotopic Mass

342.15796 Da

IUPAC Name

(1'S,3S,11'S)-6'-ethyl-11'-hydroxy-1-methoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0^{4,8}]undecan]-5'-en-2-one

Traditional Name

(1'S,3S,11'S)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0^{4,8}]undecan]-5'-en-2-one

CAS Registry Number

Not Available

SMILES

CCC1=NC2C[C@]3([C@@H]4OCC2C1[C@@H]4O)C(=O)N(OC)C1=CC=CC=C31

InChI Identifier

InChI=1S/C19H22N2O4/c1-3-12-15-10-9-25-17(16(15)22)19(8-13(10)20-12)11-6-4-5-7-14(11)21(24-2)18(19)23/h4-7,10,13,15-17,22H,3,8-9H2,1-2H3/t10?,13?,15?,16-,17+,19-/m0/s1

InChI Key

FLDAHLDTMBMPJD-MUNBIJQLSA-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
Gelsemium sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Oxepane
Benzenoid
Oxane
Pyrroline
Cyclic alcohol
Secondary alcohol
Ketimine
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Alcohol
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	1.1	ChemAxon
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	5.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.02 m³·mol⁻¹	ChemAxon
Polarizability	35.53 Å³	ChemAxon
Number of Rings	5	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

C00025091

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

102233650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Y, Wang H, Wu S, Li D, Chen S: Effect of Gelsemium elegans and Mussaenda pubescens, the Components of a Detoxification Herbal Formula, on Disturbance of the Intestinal Absorptions of Indole Alkaloids in Caco-2 Cells. Evid Based Complement Alternat Med. 2017;2017:6947948. doi: 10.1155/2017/6947948. Epub 2017 Oct 16. [PubMed:29234422 ]
Li Y, Zeng RJ, Lu Q, Wu SS, Chen JZ: Ultrasound/microwave-assisted extraction and comparative analysis of bioactive/toxic indole alkaloids in different medicinal parts of Gelsemium elegans Benth by ultra-high performance liquid chromatography with MS/MS. J Sep Sci. 2014 Feb;37(3):308-13. doi: 10.1002/jssc.201300975. Epub 2013 Dec 23. [PubMed:24375943 ]
LOTUS database [Link]

Showing NP-Card for (1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one (NP0317444)

MOL for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D MOL for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D SDF for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D-SDF for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

PDB for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D PDB for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

SMILES for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

INCHI for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

Structure for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D Structure for NP0317444 ((1's,3s,11's)-6'-ethyl-11'-hydroxy-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)