NP-MRD: Showing NP-Card for (1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one (NP0249692)

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Record Information

Version

2.0

Created at

2022-09-07 12:19:46 UTC

Updated at

2024-09-12 20:52:35 UTC

NP-MRD ID

NP0249692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one

Description

(1'S,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]Decan]-2-one 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,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one is found in Gelsemium sempervirens. Based on a literature review very few articles have been published on (1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]Decan]-2-one.

Structure

MOL SDF PDB SMILES InChI

NP0249692
  Mrv2104 05272323243D          

 52 56  0  0  0  0            999 V2000
    5.7976   -0.1966    0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1286    1.0113    0.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1482    0.6038   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5246    0.6765   -1.9145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6913    0.1061   -0.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4449    0.1767    1.1210 N   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -1.1371    1.1055 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2626   -1.0680    1.2351 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4201   -0.0968    0.2530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5464    1.3269    0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    1.9799    1.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765    1.6849    0.7999 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4003    2.7890    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3630    3.9185    0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    0.6243    0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0791    0.5722    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -0.6160    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0550   -0.5824    0.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7308   -1.7617   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -1.7138   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4938   -1.6415   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.4621    0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596   -0.0301   -1.1325 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4124   -1.3857   -1.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -2.0131   -1.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4689   -1.4203   -0.2599 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5871    0.7715   -1.2103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9471    0.8048   -2.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -0.8130    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0774   -0.8297    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578    0.1203    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8896    1.6543   -0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210    1.6265    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945    0.9800    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668   -1.8013    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -0.8000    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194   -2.0876    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552    3.7321   -0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310    4.1645    0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963    4.7707    1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780    1.4275    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8064   -1.5704   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5033   -2.6031    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4958   -2.0029   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -2.6448   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.4937   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328    0.4423   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465   -1.9514   -2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4831   -3.0753   -1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108   -1.9747   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.8158   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    0.9929   -2.6953 H   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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26  5  1  0  0  0  0
 27  5  1  0  0  0  0
 26  7  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  0  0  0  0
  2 33  1  0  0  0  0
  6 34  1  0  0  0  0
  7 35  1  1  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 16 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 23 47  1  6  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  1  0  0  0
 27 51  1  1  0  0  0
 28 52  1  0  0  0  0
M  END

NP0249692
  Mrv2104 05272323243D          

 52 56  0  0  0  0            999 V2000
    5.7976   -0.1966    0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1286    1.0113    0.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1482    0.6038   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5246    0.6765   -1.9145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6913    0.1061   -0.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4449    0.1767    1.1210 N   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -1.1371    1.1055 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2626   -1.0680    1.2351 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4201   -0.0968    0.2530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5464    1.3269    0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    1.9799    1.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765    1.6849    0.7999 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4003    2.7890    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3630    3.9185    0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    0.6243    0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0791    0.5722    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -0.6160    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0550   -0.5824    0.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7308   -1.7617   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -1.7138   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4938   -1.6415   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.4621    0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596   -0.0301   -1.1325 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4124   -1.3857   -1.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -2.0131   -1.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4689   -1.4203   -0.2599 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5871    0.7715   -1.2103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9471    0.8048   -2.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -0.8130    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0774   -0.8297    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578    0.1203    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8896    1.6543   -0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210    1.6265    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945    0.9800    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668   -1.8013    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -0.8000    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194   -2.0876    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552    3.7321   -0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310    4.1645    0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963    4.7707    1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780    1.4275    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8064   -1.5704   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5033   -2.6031    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4958   -2.0029   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -2.6448   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.4937   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328    0.4423   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465   -1.9514   -2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4831   -3.0753   -1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108   -1.9747   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.8158   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    0.9929   -2.6953 H   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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26  5  1  0  0  0  0
 27  5  1  0  0  0  0
 26  7  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  0  0  0  0
  2 33  1  0  0  0  0
  6 34  1  0  0  0  0
  7 35  1  1  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 16 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 23 47  1  6  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  1  0  0  0
 27 51  1  1  0  0  0
 28 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249692

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]2([H])OC([H])([H])[C@]3([H])[C@@]([H])(N([H])[C@]13C(=O)C([H])([H])C([H])([H])[H])C([H])([H])[C@@]21C(=O)N(OC([H])([H])[H])C2=C([H])C(OC([H])([H])[H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1/C20H24N2O6/c1-4-15(23)20-12-9-28-17(16(20)24)19(8-13(12)21-20)11-6-5-10(26-2)7-14(11)22(27-3)18(19)25/h5-7,12-13,16-17,21,24H,4,8-9H2,1-3H3/t12-,13+,16+,17-,19+,20-/s2

> <INCHI_KEY>
USWBRERBVGYKQZ-NFLCEXIZNA-N

> <FORMULA>
C20H24N2O6

> <MOLECULAR_WEIGHT>
388.42

> <EXACT_MASS>
388.163436501

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.095607295414815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3S,3'S,6'S,9'R,10'R)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-1,2-dihydro-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0^{3,9}]decan]-2-one

> <JCHEM_LOGP>
0.5489616020000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.824905122172684

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.187270256133383

> <JCHEM_PKA_STRONGEST_BASIC>
7.871383121165353

> <JCHEM_POLAR_SURFACE_AREA>
97.33000000000001

> <JCHEM_REFRACTIVITY>
97.00330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3S,3'S,6'S,9'R,10'R)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0^{3,9}]decan]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0249692                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       5.798  -0.197   0.981  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.129   1.011   0.356  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.148   0.604  -0.731  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.525   0.677  -1.915  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.691   0.106  -0.353  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.445   0.177   1.121  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.785  -1.137   1.105  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.263  -1.068   1.235  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.420  -0.097   0.253  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.546   1.327   0.878  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.378   1.980   1.345  0.00  0.00           O+0
HETATM   12  N   UNK     0      -1.877   1.685   0.800  0.00  0.00           N+0
HETATM   13  O   UNK     0      -2.400   2.789   1.482  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.363   3.918   0.615  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.699   0.624   0.457  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.079   0.572   0.437  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.686  -0.616   0.021  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.055  -0.582   0.025  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.731  -1.762  -0.393  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.893  -1.714  -0.361  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.494  -1.642  -0.325  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.903  -0.462   0.098  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.260  -0.030  -1.133  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.412  -1.386  -1.618  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.677  -2.013  -1.403  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.469  -1.420  -0.260  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.587   0.772  -1.210  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.947   0.805  -2.607  0.00  0.00           O+0
HETATM   29  H   UNK     0       6.284  -0.813   0.217  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.077  -0.830   1.507  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.558   0.120   1.701  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.890   1.654  -0.102  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.621   1.627   1.105  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.895   0.980   1.454  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.167  -1.801   1.893  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.002  -0.800   2.268  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.119  -2.088   1.095  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.955   3.732  -0.287  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.331   4.165   0.345  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.796   4.771   1.145  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.678   1.428   0.730  0.00  0.00           H+0
HETATM   42  H   UNK     0      -7.806  -1.570  -0.331  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.503  -2.603   0.270  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.496  -2.003  -1.435  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.340  -2.645  -0.697  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.894  -2.494  -0.632  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.433   0.442  -1.843  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.247  -1.951  -2.337  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.483  -3.075  -1.222  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.411  -1.975  -0.133  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.447   1.816  -0.916  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.905   0.993  -2.695  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3   32   33                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26   27                                             
CONECT    6    5    7   34                                                  
CONECT    7    6    8   26   35                                             
CONECT    8    7    9   36   37                                             
CONECT    9    8   10   23   22                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13   38   39   40                                             
CONECT   15   12   16   22                                                  
CONECT   16   15   17   41                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   42   43   44                                             
CONECT   20   17   21   45                                                  
CONECT   21   20   22   46                                                  
CONECT   22   21    9   15                                                  
CONECT   23    9   24   27   47                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   48   49                                             
CONECT   26   25    5    7   50                                             
CONECT   27   23   28    5   51                                             
CONECT   28   27   52                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    2                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O₆

Average Mass

388.4200 Da

Monoisotopic Mass

388.16344 Da

IUPAC Name

(1'S,3S,3'S,6'S,9'R,10'R)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-1,2-dihydro-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0^{3,9}]decan]-2-one

Traditional Name

(1'S,3S,3'S,6'S,9'R,10'R)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0^{3,9}]decan]-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@@]2([H])OC([H])([H])[C@]3([H])[C@@]([H])(N([H])[C@]13C(=O)C([H])([H])C([H])([H])[H])C([H])([H])[C@@]21C(=O)N(OC([H])([H])[H])C2=C([H])C(OC([H])([H])[H])=C([H])C([H])=C12

InChI Identifier

InChI=1/C20H24N2O6/c1-4-15(23)20-12-9-28-17(16(20)24)19(8-13(12)21-20)11-6-5-10(26-2)7-14(11)22(27-3)18(19)25/h5-7,12-13,16-17,21,24H,4,8-9H2,1-3H3/t12-,13+,16+,17-,19+,20-/s2

InChI Key

USWBRERBVGYKQZ-NFLCEXIZNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gelsemium sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound 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
Azepane
Oxepane
Aralkylamine
Gamma-aminoketone
Oxane
Benzenoid
Alpha-aminoketone
Cyclic alcohol
Secondary alcohol
Amino acid or derivatives
Ketone
Azetidine
Secondary amine
Azacycle
Oxacycle
Carboxylic acid derivative
Ether
Secondary aliphatic amine
Dialkyl ether
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Amine
Organooxygen compound
Organic nitrogen 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	0.55	ChemAxon
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	7.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97 m³·mol⁻¹	ChemAxon
Polarizability	40.1 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

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

Not Available

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,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one (NP0249692)

MOL for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

3D MOL for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

3D SDF for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

3D-SDF for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

PDB for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

3D PDB for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

SMILES for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

INCHI for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

Structure for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)

3D Structure for NP0249692 ((1's,3s,3's,6's,9'r,10'r)-10'-hydroxy-1,6-dimethoxy-1'-propanoyl-7'-oxa-2'-azaspiro[indole-3,5'-tricyclo[4.3.1.0³,⁹]decan]-2-one)