NP-MRD: Showing NP-Card for methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate (NP0256073)

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Record Information

Version

2.0

Created at

2022-09-07 20:47:16 UTC

Updated at

2022-09-07 20:47:16 UTC

NP-MRD ID

NP0256073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate

Description

Methyl (1'S,3S,4'R,4'aS,10'aS,10'bS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate is found in Kopsia arborea. Based on a literature review very few articles have been published on methyl (1'S,3S,4'R,4'aS,10'aS,10'bS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222472D          

 27 31  0  0  1  0            999 V2000
    6.6766   -1.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462   -1.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2488   -1.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -2.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184   -1.0815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4853   -0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    0.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -0.3144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3271    0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0906   -1.1387    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8210   -1.5223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8540   -2.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1566   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -2.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6524   -2.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -2.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.3562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8048   -1.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1573   -1.6441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718   -0.3085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456   -0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8507    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670    0.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1783    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568   -0.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3932   -1.5795    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
  5  3  1  6  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  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  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
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  0  0  0  0
 17 27  1  0  0  0  0
 10 27  1  1  0  0  0
 27 14  1  6  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    3.0907    3.8073   -0.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    2.4809   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501    1.3726    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5368    1.6073    1.4206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570   -0.0270   -0.1729 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1456   -0.9585    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995   -1.4416    1.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837   -2.0296    0.7810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4223   -3.1259    1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969   -0.8968    0.1970 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3794   -0.1492   -0.6769 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4358   -0.7966   -2.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0719   -0.6332   -2.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9038   -1.2047   -1.8953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554   -1.1015   -2.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029   -1.0555   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046   -0.6514    0.0011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5069   -1.2001    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440   -2.5385    1.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6262   -0.2585    2.1754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353    0.9878    1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334    2.2877    2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    3.3797    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172    3.1649   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224    1.8630   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0228    0.7757    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -1.2989   -0.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7349    4.2700   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    3.7398    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    4.3687    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141   -0.2046   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -1.8485    0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511   -0.4636    1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -2.4605   -0.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978   -3.8097    0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256   -3.8047    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -2.8111    2.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239   -0.2060    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.8619   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762   -1.8524   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.2198   -2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -1.1194   -3.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0119    0.4507   -2.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680   -0.2802   -3.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5141   -2.0472   -2.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4880   -2.0560   -0.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9164   -0.3090   -1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016   -2.7662    1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5783    2.4574    3.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201    4.3887    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703    3.9795   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4677    1.7753   -1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -2.3929   -0.2674 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 27  1  0
 27 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  5  1  0
 11 10  1  0
 17 27  1  0
 26 17  1  0
 26 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  6
  6 32  1  0
  6 33  1  0
  8 34  1  6
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 27 53  1  6
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 13 42  1  0
 13 43  1  0
 12 40  1  0
 12 41  1  0
 11 39  1  6
M  END


  Mrv1652309072222472D          

 27 31  0  0  1  0            999 V2000
    6.6766   -1.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462   -1.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2488   -1.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -2.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184   -1.0815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4853   -0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    0.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -0.3144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3271    0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0906   -1.1387    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8210   -1.5223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8540   -2.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1566   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -2.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6524   -2.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -2.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.3562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8048   -1.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1573   -1.6441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718   -0.3085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456   -0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8507    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670    0.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1783    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568   -0.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3932   -1.5795    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
  5  3  1  6  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  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  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
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  0  0  0  0
 17 27  1  0  0  0  0
 10 27  1  1  0  0  0
 27 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0256073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1CO[C@@H](C)[C@@H]2[C@@H]3N(CC[C@@]33C(O)=NC4=CC=CC=C34)CC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O4/c1-12-17-13(14(11-27-12)19(24)26-2)7-9-23-10-8-21(18(17)23)15-5-3-4-6-16(15)22-20(21)25/h3-6,12-14,17-18H,7-11H2,1-2H3,(H,22,25)/t12-,13+,14-,17-,18-,21-/m0/s1

> <INCHI_KEY>
VAKVMFAPWWZUCY-PFQUMEBCSA-N

> <FORMULA>
C21H26N2O4

> <MOLECULAR_WEIGHT>
370.449

> <EXACT_MASS>
370.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.22948150399971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'S,3S,4'R,4'aS,10'aS,10'bS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate

> <JCHEM_LOGP>
-0.6003331847074905

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6236274606207153

> <JCHEM_PKA_STRONGEST_BASIC>
11.178294023151746

> <JCHEM_POLAR_SURFACE_AREA>
71.36

> <JCHEM_REFRACTIVITY>
102.14110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,3S,4'R,4'aS,10'aS,10'bS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      12.463  -2.628   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.100  -1.912   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.798  -2.735   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.859  -4.274   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.434  -2.019   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.373  -0.480   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.009   0.236   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.707  -0.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.344   0.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.769  -2.126   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.133  -2.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.194  -4.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.892  -5.203   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.529  -4.487   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.085  -5.021   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.130  -3.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.985  -2.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.502  -2.115   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.294  -3.069   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.441  -0.576   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.885  -0.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.455   1.389   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.978   1.611   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.933   0.403   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.363  -1.028   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.839  -1.250   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.467  -2.948   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   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   27                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26   27                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   17                                                  
CONECT   27   17   10   14                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1's,3S,4'r,4'as,10'as,10'BS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₆N₂O₄

Average Mass

370.4490 Da

Monoisotopic Mass

370.18926 Da

IUPAC Name

methyl (1'S,3S,4'R,4'aS,10'aS,10'bS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate

Traditional Name

methyl (1'S,3S,4'R,4'aS,10'aS,10'bS)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1CO[C@@H](C)[C@@H]2[C@@H]3N(CC[C@@]33C(O)=NC4=CC=CC=C34)CC[C@H]12

InChI Identifier

InChI=1S/C21H26N2O4/c1-12-17-13(14(11-27-12)19(24)26-2)7-9-23-10-8-21(18(17)23)15-5-3-4-6-16(15)22-20(21)25/h3-6,12-14,17-18H,7-11H2,1-2H3,(H,22,25)/t12-,13+,14-,17-,18-,21-/m0/s1

InChI Key

VAKVMFAPWWZUCY-PFQUMEBCSA-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
Kopsia arborea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimban skeleton
Yohimbine alkaloid
3-alkylindole
Indole or derivatives
Indolizidine
Aralkylamine
Oxane
Piperidine
Benzenoid
N-alkylpyrrolidine
Cyclic carboximidic acid
Pyrrolidine
Methyl ester
Carboxylic acid ester
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Amine
Organopnictogen compound
Organic oxygen 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	-0.6	ChemAxon
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	11.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.14 m³·mol⁻¹	ChemAxon
Polarizability	39.23 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

163043002

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,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate (NP0256073)

MOL for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

3D MOL for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

3D SDF for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

3D-SDF for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

PDB for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

3D PDB for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

SMILES for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

INCHI for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

Structure for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)

3D Structure for NP0256073 (methyl (1's,3s,4'r,4'as,10'as,10'bs)-2-hydroxy-1'-methyl-1',3',4',4'a,5',6',8',9',10'a,10'b-decahydrospiro[indole-3,10'-pyrano[4,3-g]indolizine]-4'-carboxylate)