NP-MRD: Showing NP-Card for methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (NP0273700)

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Record Information

Version

2.0

Created at

2022-09-08 20:49:40 UTC

Updated at

2022-09-08 20:49:41 UTC

NP-MRD ID

NP0273700

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

Description

Isopteropodin 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. methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate is found in Catharanthus roseus, Mitragyna diversifolia, Mitragyna hirsuta, Mitragyna inermis, Mitragyna parvifolia, Mitragyna rotundifolia, Mitragyna speciosa, Fleroya stipulosa, Mitragyna tubulosa, Uncaria elliptica, Uncaria guianensis, Uncaria hirsuta, Uncaria homomalla, Uncaria sinensis and Uncaria tomentosa. Isopteropodin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151519062D          

 27 31  0  0  0  0            999 V2000
    4.3015    2.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6239    1.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085    0.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497    0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686   -0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5909   -0.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0944   -1.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756   -1.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -2.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602   -1.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3376   -2.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160   -1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6379   -1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344   -0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -2.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -0.5401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -0.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -0.4237    0.0000 C   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
  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  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 15 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -4.7087    3.4738    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4260    2.1002    0.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1944    1.5428    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3477    2.3646    0.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633    0.1138    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584   -0.6145   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8065   -1.9777   -0.4270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -2.6724   -0.0287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7000   -3.0768    1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -1.7064   -0.3210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1433   -2.2992   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -1.3268   -0.4616 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9477   -0.8235   -1.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4032    0.6046   -1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632    0.7601   -0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6497    2.1431    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6552    2.9079    0.3316 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9595    2.5779    0.4977 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8718    1.5014    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2487    1.4626    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9070    0.2816    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.8559   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -0.7936   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1678    0.4009   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8135   -0.1833    0.4174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5331    0.4576    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6717   -0.5100    0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8535    3.7348    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6626    3.6700   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8705    4.1060   -0.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.1696   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4907   -3.5683   -0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860   -2.3288    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930   -3.3755    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -3.9984    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.3598   -1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0432   -2.7067    0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0286   -3.1160   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333   -1.4115   -2.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144   -0.9408   -2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5313    1.2431   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729    0.8126   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2591    3.5491    0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848    2.3252    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9694    0.2567    0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7747   -1.7625   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3308   -1.6672   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257   -0.4647    1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192    1.1532   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    1.0638    1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -0.8975    1.6172 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 25  1  0
 25 26  1  0
 26 27  1  0
 15 16  1  1
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 27  5  1  0
 24 19  1  0
 27 10  1  0
 25 12  1  0
 24 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  8 32  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  0
 11 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 25 48  1  1
 26 49  1  0
 26 50  1  0
 27 51  1  1
 18 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
M  END


  Mrv1533004151519062D          

 27 31  0  0  0  0            999 V2000
    4.3015    2.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6239    1.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085    0.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497    0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686   -0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5909   -0.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0944   -1.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756   -1.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -2.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602   -1.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3376   -2.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160   -1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6379   -1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344   -0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -2.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -0.5401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -0.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -0.4237    0.0000 C   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
  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  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 15 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273700

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(C)C2CN3CCC4(C3CC12)C(=O)NC1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)

> <INCHI_KEY>
JMIAZDVHNCCPDM-UHFFFAOYSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.13844942530501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.7049254469999995

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.167255479052887

> <JCHEM_PKA_STRONGEST_BASIC>
10.747925133916349

> <JCHEM_POLAR_SURFACE_AREA>
67.87

> <JCHEM_REFRACTIVITY>
101.39240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.030   4.180   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.631   2.762   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.704   1.532   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.176   1.720   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.306   0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.835  -0.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.436  -1.491   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.510  -2.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.111  -4.138   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.981  -2.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.054  -3.763   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.526  -3.575   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.363  -4.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.043  -3.792   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.390  -2.292   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924  -2.157   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.851  -0.927   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.379  -1.115   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.856  -2.426   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.063  -3.746   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       1.254  -1.008   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.416   0.002   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.443   1.542   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.790   2.289   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.110   1.495   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.083  -0.044   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.736  -0.791   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   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19   27                                             
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    5   10                                                  
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   15   22                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-F]indolizine]-4'-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(C)C2CN3CCC4(C3CC12)C(=O)NC1=CC=CC=C41

InChI Identifier

InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)

InChI Key

JMIAZDVHNCCPDM-UHFFFAOYSA-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
Catharanthus roseus	LOTUS Database	35616633
Mitragyna diversifolia	LOTUS Database	35616633
Mitragyna hirsuta	LOTUS Database	35616633
Mitragyna inermis	LOTUS Database	35616633
Mitragyna parvifolia	LOTUS Database	35616633
Mitragyna rotundifolia	LOTUS Database	35616633
Mitragyna speciosa	LOTUS Database	35616633
Mitragyna stipulosa	LOTUS Database	35616633
Mitragyna tubulosa	LOTUS Database	35616633
Uncaria elliptica	LOTUS Database	35616633
Uncaria guianensis	LOTUS Database	35616633
Uncaria hirsuta	LOTUS Database	35616633
Uncaria homomalla	LOTUS Database	35616633
Uncaria sinensis	LOTUS Database	35616633
Uncaria tomentosa	LOTUS Database	35616633

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
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxamide group
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid ester
Lactam
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen 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	2.31	ALOGPS
logP	1.7	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	10.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.39 m³·mol⁻¹	ChemAxon
Polarizability	39.14 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

98363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (NP0273700)

MOL for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D MOL for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D SDF for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D-SDF for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

PDB for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D PDB for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

SMILES for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

INCHI for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

Structure for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D Structure for NP0273700 (methyl 2-hydroxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)