NP-MRD: Showing NP-Card for (1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate (NP0167996)

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Record Information

Version

2.0

Created at

2022-09-03 03:41:52 UTC

Updated at

2022-09-03 03:41:53 UTC

NP-MRD ID

NP0167996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate

Description

Methyl (1'S,3S,4'aS,5'aS,9'S,10'aR)-2-hydroxy-1'-methyl-9'-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. (1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate is found in Mitragyna hirsuta. Based on a literature review very few articles have been published on methyl (1'S,3S,4'aS,5'aS,9'S,10'aR)-2-hydroxy-1'-methyl-9'-oxo-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205412D          

 28 32  0  0  1  0            999 V2000
    3.4824   -0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566    0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754    0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342    1.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    1.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930    2.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    3.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3672    3.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    2.9491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0049    3.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    3.5074    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    4.5825    4.2963    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.4464    4.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1535    3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679    2.8198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7898    2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147    3.5989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1122    2.1323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4751    0.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0464    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7824    2.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461    2.7480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6496    2.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307    2.1896    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  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 20 25  1  0  0  0  0
 16 25  1  0  0  0  0
 16 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
 28 27  1  6  0  0  0
  5 28  1  0  0  0  0
 10 28  1  0  0  0  0
M  CHG  2  12   1  13  -1
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -2.8276    4.5474    1.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755    3.1443    1.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703    2.2574    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    2.8244    0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3235    0.8169    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2476    0.3632    1.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862   -0.9829    2.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968   -1.9068    1.0302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9861   -1.9400   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6135   -1.5480    0.6178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0323   -2.3865   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3880   -2.0472   -0.5242 N   0  0  1  0  0  4  0  0  0  0  0  0
    0.9642   -2.3974    0.6470 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.1286   -2.6601   -1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -1.8672   -1.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -0.4543   -1.1876 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0146    0.3650   -2.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.0815   -3.6169 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7646    1.3619   -2.2167 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914    1.3699   -0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404    2.2318   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5126    2.0133    1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0404    0.9105    1.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909    0.0499    1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8091    0.2628   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583   -0.6439   -0.8070 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0155    0.1983    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -0.0853    0.2567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3009    4.9114    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2569    5.0143    2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    4.7493    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861    1.0437    2.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0074   -2.8978    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0027   -1.7571    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394   -1.1202   -0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0633   -2.9315   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -1.6985    1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4488   -2.1491   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -3.4637   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -3.7298   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6901   -2.3978   -2.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -2.2802   -0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950   -1.8462   -2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.3816   -4.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4915    3.0900   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1737    2.6922    1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290    0.7303    2.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574   -0.7971    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -0.4135   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2818    1.2257    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -0.2083    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620   -0.0270   -0.8443 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  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
 16 17  1  6
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 28  5  1  0
 25 20  1  0
 28 10  1  0
 26 12  1  0
 25 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 26 49  1  6
 27 50  1  0
 27 51  1  0
 28 52  1  6
 18 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
M  CHG  2  12   1  13  -1
M  END


  Mrv1652309032205412D          

 28 32  0  0  1  0            999 V2000
    3.4824   -0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566    0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754    0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342    1.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    1.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930    2.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    3.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3672    3.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    2.9491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0049    3.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    3.5074    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    4.5825    4.2963    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.4464    4.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1535    3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679    2.8198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7898    2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147    3.5989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1122    2.1323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4751    0.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0464    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7824    2.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461    2.7480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6496    2.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307    2.1896    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  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 20 25  1  0  0  0  0
 16 25  1  0  0  0  0
 16 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
 28 27  1  6  0  0  0
  5 28  1  0  0  0  0
 10 28  1  0  0  0  0
M  CHG  2  12   1  13  -1
M  END
> <DATABASE_ID>
NP0167996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@H]2C[N@@+]3([O-])CC[C@]4([C@@H]3C[C@H]12)C(O)=NC1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O5/c1-12-14-10-23(26)8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-28-12)19(24)27-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21-,23-/m0/s1

> <INCHI_KEY>
DTEXPPFMGPLSPX-LKYWSZFDSA-N

> <FORMULA>
C21H24N2O5

> <MOLECULAR_WEIGHT>
384.432

> <EXACT_MASS>
384.168521881

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.98144459994644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3S,4'aS,5'aS,9'S,10'aR)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-4'a,5',5'a,7',8',9',10',10'a-octahydro-1'H-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.6215587470230001

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1552251153732698

> <JCHEM_PKA_STRONGEST_BASIC>
3.907107282884729

> <JCHEM_POLAR_SURFACE_AREA>
91.18

> <JCHEM_REFRACTIVITY>
104.1924

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3S,4'aS,5'aS,9'S,10'aR)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.500  -1.208   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.899   0.210   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.826   1.440   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.354   1.252   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.224   2.857   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.695   3.045   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.094   4.463   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.020   5.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.419   7.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.549   5.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.476   6.735   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.004   6.547   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0       8.554   8.020   0.000  0.00  0.00           O-1
HETATM   14  C   UNK     0      10.167   7.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.487   6.764   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.140   5.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.674   5.398   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.467   6.718   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      13.276   3.980   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      12.114   2.970   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.087   1.430   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.740   0.684   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.420   1.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.447   3.017   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.794   3.763   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.606   5.130   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.679   3.900   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.151   4.087   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   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   26                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25   26                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   16                                                  
CONECT   26   16   12   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1's,3S,4'as,5'as,9's,10'ar)-2-hydroxy-1'-methyl-9'-oxo-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

C₂₁H₂₄N₂O₅

Average Mass

384.4320 Da

Monoisotopic Mass

384.16852 Da

IUPAC Name

(1'S,3S,4'aS,5'aS,9'S,10'aR)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-4'a,5',5'a,7',8',9',10',10'a-octahydro-1'H-spiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate

Traditional Name

(1'S,3S,4'aS,5'aS,9'S,10'aR)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](C)[C@H]2C[N@@+]3([O-])CC[C@]4([C@@H]3C[C@H]12)C(O)=NC1=CC=CC=C41

InChI Identifier

InChI=1S/C21H24N2O5/c1-12-14-10-23(26)8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-28-12)19(24)27-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21-,23-/m0/s1

InChI Key

DTEXPPFMGPLSPX-LKYWSZFDSA-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
Mitragyna hirsuta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Indolizidine
Benzenoid
N-alkylpyrrolidine
Piperidine
Trialkyl amine oxide
Vinylogous ester
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Carboxylic acid ester
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Trisubstituted n-oxide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
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	0.92	ALOGPS
logP	0.62	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	3.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.19 m³·mol⁻¹	ChemAxon
Polarizability	39.98 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

163190246

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate (NP0167996)

MOL for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

3D MOL for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

3D SDF for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

3D-SDF for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

PDB for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

3D PDB for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

SMILES for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

INCHI for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

Structure for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)

3D Structure for NP0167996 ((1's,3s,4'as,5'as,9's,10'ar)-2-hydroxy-4'-(methoxycarbonyl)-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizin]-9'-ium-9'-olate)