NP-MRD: Showing NP-Card for 9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid (NP0218522)

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Record Information

Version

2.0

Created at

2022-09-05 19:12:53 UTC

Updated at

2022-09-05 19:12:53 UTC

NP-MRD ID

NP0218522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid

Description

9-Hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]Icosa-2(7),3,5,14-tetraene-13-carboxylic acid belongs to the class of organic compounds known as melodinus alkaloids. These are alkaloids with a structure that is based on the melodinus skeleton. This backbone is a pentacyclic structure that contains a tetrahydroquinoline and an indolizine joined to each other through a cyclopentane. 9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid is found in Kopsia singapurensis. 9-Hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]Icosa-2(7),3,5,14-tetraene-13-carboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181501032D          

 34 38  0  0  0  0            999 V2000
    7.1518   -1.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -1.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7229   -1.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -2.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -1.2276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7172    0.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331   -0.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1461    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7143    0.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984    1.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -0.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5752   -0.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864    0.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564    0.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275    0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304   -0.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1491   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650   -1.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781   -1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940   -1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6838   -2.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9092   -2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -3.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -2.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -3.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -1.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -0.4175    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 31  1  0  0  0  0
 14 31  1  0  0  0  0
 17 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END


  Mrv1533004181501032D          

 34 38  0  0  0  0            999 V2000
    7.1518   -1.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -1.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7229   -1.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -2.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -1.2276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7172    0.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331   -0.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1461    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7143    0.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984    1.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -0.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5752   -0.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864    0.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564    0.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275    0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304   -0.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1491   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650   -1.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781   -1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940   -1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6838   -2.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9092   -2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -3.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -2.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -3.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -1.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -0.4175    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 31  1  0  0  0  0
 14 31  1  0  0  0  0
 17 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(OC)C=CC=C2C23CCN4CC=CC(CCC2C1(O)C(=O)OC)(C34)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O8/c1-32-15-7-4-6-14-17(15)26(21(30)34-3)24(31,20(29)33-2)16-8-10-22(19(27)28)9-5-12-25-13-11-23(14,16)18(22)25/h4-7,9,16,18,31H,8,10-13H2,1-3H3,(H,27,28)

> <INCHI_KEY>
HTNHBWITZORDGY-UHFFFAOYSA-N

> <FORMULA>
C24H28N2O8

> <MOLECULAR_WEIGHT>
472.494

> <EXACT_MASS>
472.18456587

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.84769110229004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
-0.9442763716917421

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.38271263169455

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8626876600133246

> <JCHEM_PKA_STRONGEST_BASIC>
9.03600402767625

> <JCHEM_POLAR_SURFACE_AREA>
125.84000000000002

> <JCHEM_REFRACTIVITY>
119.05559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      13.350  -3.048   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.014  -2.282   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.683  -3.057   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.688  -4.597   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.346  -2.291   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.341  -0.751   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.672   0.023   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.008  -0.742   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.339   0.032   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.667   1.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.330   2.329   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.999   1.554   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.426  -0.097   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.674  -0.761   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.815   0.274   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.183   1.678   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.332   1.545   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.996   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.665   1.535   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.670  -0.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.006  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.012  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.348  -3.075   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.679  -2.301   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.015  -3.066   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.743  -4.423   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.297  -4.428   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.118  -5.731   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.758  -4.487   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.040  -5.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.337   0.005   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.675  -1.545   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.681  -3.085   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.339  -0.779   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   24   31                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31   32                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   14   25                                                  
CONECT   25   24    5   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   21   14   17                                                  
CONECT   32   21   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0,.0,.0,]icosa-2(7),3,5,14-tetraene-13-carboxylate	Generator
9-Hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2(7),3,5,14-tetraene-13-carboxylate	Generator

Chemical Formula

C₂₄H₂₈N₂O₈

Average Mass

472.4940 Da

Monoisotopic Mass

472.18457 Da

IUPAC Name

9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid

Traditional Name

9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(OC)C=CC=C2C23CCN4CC=CC(CCC2C1(O)C(=O)OC)(C34)C(O)=O

InChI Identifier

InChI=1S/C24H28N2O8/c1-32-15-7-4-6-14-17(15)26(21(30)34-3)24(31,20(29)33-2)16-8-10-22(19(27)28)9-5-12-25-13-11-23(14,16)18(22)25/h4-7,9,16,18,31H,8,10-13H2,1-3H3,(H,27,28)

InChI Key

HTNHBWITZORDGY-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
Kopsia singapurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melodinus alkaloids. These are alkaloids with a structure that is based on the melodinus skeleton. This backbone is a pentacyclic structure that contains a tetrahydroquinoline and an indolizine joined to each other through a cyclopentane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Melodinus alkaloids

Sub Class

Not Available

Direct Parent

Melodinus alkaloids

Alternative Parents

Substituents

Melodinus skeleton
Benzoquinoline
Phenanthridine
1,8-phenanthroline
Alpha-amino acid ester
Tetrahydroquinoline
Alpha-amino acid or derivatives
Quinoline
Indole or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
N-alkylpyrrolidine
Methyl ester
Carbamic acid ester
Pyrrolidine
Carboxylic acid ester
Amino acid or derivatives
Amino acid
Carbonic acid derivative
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Organoheterocyclic compound
Alkanolamine
Ether
Carboxylic acid
Azacycle
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen 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	1.22	ALOGPS
logP	-0.94	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.86	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	125.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.06 m³·mol⁻¹	ChemAxon
Polarizability	46.85 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid (NP0218522)

MOL for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

3D MOL for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

3D SDF for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

3D-SDF for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

PDB for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

3D PDB for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

SMILES for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

INCHI for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

Structure for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)

3D Structure for NP0218522 (9-hydroxy-6-methoxy-8,9-bis(methoxycarbonyl)-8,17-diazapentacyclo[11.6.1.0¹,¹⁰.0²,⁷.0¹⁷,²⁰]icosa-2,4,6,14-tetraene-13-carboxylic acid)