NP-MRD: Showing NP-Card for methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (NP0222254)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 00:02:51 UTC

Updated at

2022-09-06 00:02:51 UTC

NP-MRD ID

NP0222254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

Description

Isoreserpiline pseudoindoxyl belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Based on a literature review very few articles have been published on isoreserpiline pseudoindoxyl.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202022D          

 31 35  0  0  1  0            999 V2000
    5.8191   -4.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3364   -3.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6746   -2.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4953   -2.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919   -2.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3712   -2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8885   -1.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267   -0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7440   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474   -0.5973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3856    0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2063    0.2387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6935    0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4773    0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4745   -0.1781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2599    0.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7426   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5628   -0.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8957   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7159   -1.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2031   -0.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4085   -2.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415   -2.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2543   -3.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5884   -2.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2554   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4716   -1.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8025   -1.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6890   -0.4304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3508   -1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5301   -1.2664    0.0000 C   0  0  2  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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 15 29  1  0  0  0  0
 29 12  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
  5 31  1  0  0  0  0
 10 31  1  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -2.5101    3.8157   -1.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    2.4846   -1.4652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519    2.0988   -0.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589    2.9598   -0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1465    0.7396   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3242    0.4301    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5950   -0.8480    0.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976   -1.6109    0.9641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9388   -2.9904    1.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -1.6224   -0.1247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2990   -2.4424    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0121   -2.1169   -0.1062 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0322   -2.6509    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -1.4349    1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048   -0.5133    0.2686 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0111    0.8025    0.5292 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4169    0.8789    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068    1.7671    0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7367    1.5837    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7393    2.4719    0.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211    3.6171    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    0.4772   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4097    0.2880   -0.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071   -0.7842   -1.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458   -0.4316   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -0.2265   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386   -1.0136   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -1.9227   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263   -0.7401   -0.3069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8229    0.1511    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812   -0.2495   -0.5513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1313    4.0578   -2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072    4.4981   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438    3.9719   -2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1340    1.1609    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0178   -1.1607    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1869   -3.5960    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -2.8807    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108   -3.5240    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370   -2.1297   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2721   -2.3825    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -3.5116    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -3.1852    0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125   -3.2685    1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358   -1.6295    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060   -1.0175    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    1.6096    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589    2.6383    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6586    4.1897    0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298    3.3314    2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3241    4.2307    1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7287   -0.6766   -2.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4510   -1.7626   -1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9971   -0.8685   -1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4047   -1.3122   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6732   -0.5044   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0516   -0.1354    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797    1.2072    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7156   -0.3180   -1.6196 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 15 29  1  0
 29 30  1  0
 30 31  1  0
 31  5  1  0
 31 10  1  0
 29 12  1  0
 15 27  1  6
 26 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  8 36  1  1
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 18 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 29 56  1  6
 30 57  1  0
 30 58  1  0
 31 59  1  6
M  END


  Mrv1652309062202022D          

 31 35  0  0  1  0            999 V2000
    5.8191   -4.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3364   -3.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6746   -2.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4953   -2.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919   -2.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3712   -2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8885   -1.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267   -0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7440   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474   -0.5973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3856    0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2063    0.2387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6935    0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4773    0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4745   -0.1781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2599    0.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7426   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5628   -0.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8957   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7159   -1.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2031   -0.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4085   -2.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415   -2.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2543   -3.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5884   -2.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2554   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4716   -1.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8025   -1.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6890   -0.4304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3508   -1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5301   -1.2664    0.0000 C   0  0  2  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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 15 29  1  0  0  0  0
 29 12  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
  5 31  1  0  0  0  0
 10 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CC[C@]4(NC5=CC(OC)=C(OC)C=C5C4=O)[C@@H]3C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O6/c1-12-15-10-25-6-5-23(20(25)8-13(15)16(11-31-12)22(27)30-4)21(26)14-7-18(28-2)19(29-3)9-17(14)24-23/h7,9,11-13,15,20,24H,5-6,8,10H2,1-4H3/t12-,13-,15-,20-,23-/m0/s1

> <INCHI_KEY>
BSQCYJALKUSFFD-GCIZAMGCSA-N

> <FORMULA>
C23H28N2O6

> <MOLECULAR_WEIGHT>
428.485

> <EXACT_MASS>
428.19473663

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.017783368327585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1'S,2S,4'aS,5'aS,10'aS)-5,6-dimethoxy-1'-methyl-3-oxo-1,1',3,4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

> <JCHEM_LOGP>
1.8140836753333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.557383413838323

> <JCHEM_PKA_STRONGEST_BASIC>
9.477979446462717

> <JCHEM_POLAR_SURFACE_AREA>
86.33000000000001

> <JCHEM_REFRACTIVITY>
114.60949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,2S,4'aS,5'aS,10'aS)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1H-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.862  -7.671   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.961  -6.422   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.593  -5.018   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.125  -4.862   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.692  -3.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.160  -3.924   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.259  -2.675   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.890  -1.271   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.989  -0.022   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.422  -1.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.053   0.290   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      11.585   0.446   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      12.495   1.688   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.958   1.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.952  -0.333   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      15.419   0.138   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      16.319  -1.111   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.850  -1.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.472  -2.686   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      20.003  -2.852   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.913  -1.609   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.563  -3.929   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      18.184  -5.338   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.275  -6.580   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.032  -3.762   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.410  -2.353   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.947  -1.873   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.698  -2.773   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.486  -0.803   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.855  -2.208   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.323  -2.364   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   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27   29                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   17   27                                                  
CONECT   27   26   15   28                                                  
CONECT   28   27                                                            
CONECT   29   15   12   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈N₂O₆

Average Mass

428.4850 Da

Monoisotopic Mass

428.19474 Da

IUPAC Name

methyl (1'S,2S,4'aS,5'aS,10'aS)-5,6-dimethoxy-1'-methyl-3-oxo-1,1',3,4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

Traditional Name

methyl (1'S,2S,4'aS,5'aS,10'aS)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1H-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CC[C@]4(NC5=CC(OC)=C(OC)C=C5C4=O)[C@@H]3C[C@H]12

InChI Identifier

InChI=1S/C23H28N2O6/c1-12-15-10-25-6-5-23(20(25)8-13(15)16(11-31-12)22(27)30-4)21(26)14-7-18(28-2)19(29-3)9-17(14)24-23/h7,9,11-13,15,20,24H,5-6,8,10H2,1-4H3/t12-,13-,15-,20-,23-/m0/s1

InChI Key

BSQCYJALKUSFFD-GCIZAMGCSA-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 indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indole or derivatives
Dihydroindole
Indolizidine
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Secondary aliphatic/aromatic amine
Piperidine
N-alkylpyrrolidine
Benzenoid
Vinylogous ester
Pyrrolidine
Vinylogous amide
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Ketone
Carboxylic acid ester
Secondary amine
Oxacycle
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	1.81	ChemAxon
pKa (Strongest Acidic)	11.56	ChemAxon
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.61 m³·mol⁻¹	ChemAxon
Polarizability	44.02 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

552800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (NP0222254)

MOL for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D MOL for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D SDF for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D-SDF for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

PDB for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D PDB for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

SMILES for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

INCHI for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

Structure for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D Structure for NP0222254 (methyl (1's,2s,4'as,5'as,10'as)-5,6-dimethoxy-1'-methyl-3-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydro-1h-spiro[indole-2,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)