NP-MRD: Showing NP-Card for (1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one (NP0149957)

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Record Information

Version

2.0

Created at

2022-09-02 05:56:04 UTC

Updated at

2022-09-02 05:56:04 UTC

NP-MRD ID

NP0149957

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

Description

GS-1 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,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one is found in Gelsemium sempervirens. Based on a literature review very few articles have been published on GS-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207562D          

 28 32  0  0  1  0            999 V2000
    7.0362    2.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7772    1.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694    1.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    1.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127    1.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9026    0.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7104    0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4864   -0.4027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181   -1.1581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6381   -1.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804   -0.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0644   -0.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983    0.5939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8063    0.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    0.8702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4490    0.3631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147    0.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059    1.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578    1.9427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    1.3809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2369    1.8518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6895    2.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    2.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    1.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6100    1.3495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6370    0.5249    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 22 18  1  1  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    6.4275    0.1203    0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.7209    1.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231    0.5369    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1224    1.0788    1.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.9259    1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    0.1976    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -0.3525   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369   -0.1881    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7943   -1.1118   -1.2390 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004   -1.7741   -2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850   -2.9932   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870   -1.0086   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -1.6662   -1.8632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463   -0.0949    0.0370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7652   -0.6735    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -0.1771    1.2849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0728   -0.8285    0.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8395    0.0541   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2250   -0.0821   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9829   -1.3301   -0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7905    0.9056   -1.1774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9894    1.2644   -0.3113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4496    1.2411    1.1357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4124    2.2614    1.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494    2.1716    0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4658    1.2105   -0.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8027    1.0855   -1.1835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8444    1.9713   -2.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4636    0.2693    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2652    0.5418   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.9586    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152    1.6606    2.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460    1.3827    2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -0.6241   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -3.7809   -2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813   -3.1237   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -3.2092   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -0.6462    2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8569   -1.7864    0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -0.5287    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4791   -1.4035    0.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7995   -1.3828   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517   -2.2401   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    2.1884   -0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3449    1.5142    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416    2.3325    2.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    3.2589    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637    1.4831   -1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8667    0.0700   -1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    1.5175   -3.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9 12  1  0
 12 13  2  0
 14 12  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 14  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3  8  1  0
  8  7  2  0
  7  9  1  0
 26 14  1  0
  7  6  1  0
 23 16  1  0
 27 22  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  1
 22 44  1  6
 23 45  1  1
 24 46  1  0
 24 47  1  0
 26 48  1  6
 27 49  1  6
 28 50  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
  5 33  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  8 34  1  0
M  END


  Mrv1652309022207562D          

 28 32  0  0  1  0            999 V2000
    7.0362    2.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7772    1.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694    1.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    1.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127    1.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9026    0.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7104    0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4864   -0.4027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181   -1.1581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6381   -1.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804   -0.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0644   -0.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983    0.5939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8063    0.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    0.8702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4490    0.3631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147    0.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059    1.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578    1.9427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    1.3809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2369    1.8518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6895    2.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    2.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    1.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6100    1.3495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6370    0.5249    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 22 18  1  1  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0149957

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)[C@@]2(C[C@@H]3N=C([C@H]4[C@@H]3CO[C@@H]2[C@@H]4O)C(C)=O)C2=CC=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O6/c1-9(23)16-15-11-8-28-18(17(15)24)20(7-13(11)21-16)12-5-4-10(26-2)6-14(12)22(27-3)19(20)25/h4-6,11,13,15,17-18,24H,7-8H2,1-3H3/t11-,13+,15-,17-,18-,20+/m1/s1

> <INCHI_KEY>
XTCNHYCPNSGXRX-PXUXMEPPSA-N

> <FORMULA>
C20H22N2O6

> <MOLECULAR_WEIGHT>
386.404

> <EXACT_MASS>
386.147786436

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.90894514331362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3S,4'S,7'R,8'S,11'R)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0^{4,8}]undecan]-5'-en-2-one

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.5346303766666676

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.2344650045002

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.753584292116365

> <JCHEM_PKA_STRONGEST_BASIC>
2.132231974182989

> <JCHEM_POLAR_SURFACE_AREA>
97.66000000000001

> <JCHEM_REFRACTIVITY>
97.20490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3S,4'S,7'R,8'S,11'R)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      13.134   4.127   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.651   2.665   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.143   2.353   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.118   3.502   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.610   3.190   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.127   1.728   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.152   0.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.659   0.890   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.375  -0.752   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       8.994  -2.162   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.525  -2.331   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.870  -0.424   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.720  -1.448   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.717   1.109   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.238   0.551   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.012   1.624   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.705   0.678   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.707   1.864   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.198   2.167   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.820   1.011   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.295   3.626   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.095   2.578   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.176   3.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.020   4.811   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.502   4.268   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.465   2.676   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.872   2.519   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.922   0.980   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15   26                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   27                                                  
CONECT   23   22   16   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   14   27                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₆

Average Mass

386.4040 Da

Monoisotopic Mass

386.14779 Da

IUPAC Name

(1'S,3S,4'S,7'R,8'S,11'R)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-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,4'S,7'R,8'S,11'R)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-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

CON1C(=O)[C@@]2(C[C@@H]3N=C([C@H]4[C@@H]3CO[C@@H]2[C@@H]4O)C(C)=O)C2=CC=C(OC)C=C12

InChI Identifier

InChI=1S/C20H22N2O6/c1-9(23)16-15-11-8-28-18(17(15)24)20(7-13(11)21-16)12-5-4-10(26-2)6-14(12)22(27-3)19(20)25/h4-6,11,13,15,17-18,24H,7-8H2,1-3H3/t11-,13+,15-,17-,18-,20+/m1/s1

InChI Key

XTCNHYCPNSGXRX-PXUXMEPPSA-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
Anisole
Alkyl aryl ether
Oxepane
Oxane
Benzenoid
Cyclic alcohol
Pyrroline
Ketimine
Ketone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Imine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Organopnictogen compound
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	0.68	ALOGPS
logP	0.53	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	2.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.2 m³·mol⁻¹	ChemAxon
Polarizability	38.91 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

C00026738

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Southern Pacific class GS-1

METLIN ID

Not Available

PubChem Compound

12070887

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one (NP0149957)

MOL for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D MOL for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D SDF for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D-SDF for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

PDB for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D PDB for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

SMILES for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

INCHI for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

Structure for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D Structure for NP0149957 ((1's,3s,4's,7'r,8's,11'r)-6'-acetyl-11'-hydroxy-1,6-dimethoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)