NP-MRD: Showing NP-Card for methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate (NP0267743)

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Record Information

Version

2.0

Created at

2022-09-08 12:37:03 UTC

Updated at

2022-09-08 12:37:04 UTC

NP-MRD ID

NP0267743

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

Description

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system. 3-Hydroxy-16-methoxy-2,3-dihydrotabersonine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate is found in Apis cerana. methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate was first documented in 2015 (PMID: 25918424). Based on a literature review very few articles have been published on 3-hydroxy-16-methoxy-2,3-dihydrotabersonine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214372D          

 28 32  0  0  1  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -1.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786   -0.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0825    1.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351    1.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4359    2.5280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102    1.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7861    2.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  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  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
  3 27  1  0  0  0  0
 10 28  1  0  0  0  0
 28  7  1  1  0  0  0
  3 28  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -1.7120    0.1228   -3.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598   -0.7099   -2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   -0.7595   -0.7880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9679   -1.5485    0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -2.8533    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405   -3.5387   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -2.7920   -1.0316 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5886   -3.3033   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -2.4272    0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798   -1.0909    0.2338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4703   -0.3188   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -0.4438   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857    0.3777   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    1.3254   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7837    2.1547   -0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058    3.1221   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9264    1.4086    0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311    0.6134    0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099    0.4897    1.8023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370   -0.3244    1.3750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3975    0.5535    1.1661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4514    0.1486    2.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647    1.9637    1.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1470    2.5276    0.9199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156    2.6480    2.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    3.9822    2.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9389    0.6245   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6522   -1.3797   -0.8819 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4017    0.7932   -3.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    0.7088   -2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742   -0.5710   -3.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -1.7644   -2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5602   -0.2452   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686   -1.0093    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -3.4245    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1911   -4.0461   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4248   -4.4146    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -3.3051   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -4.3532   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -2.8347    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8401   -2.3790    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9350   -1.1722   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8655    0.3010   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3005    3.3552   -0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6800    4.0957   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1076    2.7960    1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1892    2.1311    1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528    0.9276    2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238   -1.0001    2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511    0.4127    2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    4.0515    3.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578    4.3472    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2911    4.6329    2.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9986    1.0061   -0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857    1.3614   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1753   -0.9734   -1.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3 27  1  0
 27 21  1  0
 21 22  1  1
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  1
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7 28  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
  4  3  1  0
 28  3  1  0
 10 20  1  0
 28 10  1  0
 11 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
 27 54  1  0
 27 55  1  0
 22 50  1  0
 20 49  1  1
 19 48  1  0
 17 47  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 13 43  1  0
 12 42  1  0
  9 40  1  0
  9 41  1  0
  8 38  1  0
  8 39  1  0
  6 36  1  0
  6 37  1  0
  5 35  1  0
  4 34  1  0
 28 56  1  6
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END


  Mrv1652309082214372D          

 28 32  0  0  1  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -1.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786   -0.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0825    1.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351    1.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4359    2.5280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102    1.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7861    2.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  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  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
  3 27  1  0  0  0  0
 10 28  1  0  0  0  0
 28  7  1  1  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12C[C@@](O)([C@@H]3NC4=CC(OC)=CC=C4[C@@]33CCN(CC=C1)[C@@H]23)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O4/c1-4-20-8-5-10-24-11-9-21(18(20)24)15-7-6-14(27-2)12-16(15)23-17(21)22(26,13-20)19(25)28-3/h5-8,12,17-18,23,26H,4,9-11,13H2,1-3H3/t17-,18+,20+,21+,22-/m1/s1

> <INCHI_KEY>
MLIQIRKAHMVCDD-MMGCJVFTSA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.8086865094927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,9R,10R,12R,19S)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <JCHEM_LOGP>
1.7252424596666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.840486025564488

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.76787882554642

> <JCHEM_PKA_STRONGEST_BASIC>
8.762773732181937

> <JCHEM_POLAR_SURFACE_AREA>
71.03

> <JCHEM_REFRACTIVITY>
107.70429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,9R,10R,12R,19S)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.276   0.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.714   0.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.910  -0.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.472  -0.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.229  -2.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.425  -3.061   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.863  -2.510   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.672  -2.928   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.512  -1.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.544  -0.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.915  -1.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.312  -2.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.799  -3.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.890  -1.940   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.377  -2.340   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.467  -1.253   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.493  -0.452   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.005  -0.052   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.308   1.321   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.786   1.082   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.591   2.052   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.754   3.061   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.799   3.373   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.547   4.719   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.259   3.348   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.467   4.668   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.152   1.502   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.106  -0.990   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27   28                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20   28                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   10   21                                                  
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   21    3                                                       
CONECT   28   10    7    3                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
16-Methoxy-2,3-dihydro-3-hydroxytabersonine	ChEBI
(3R)-3-Hydroxy-16-methoxy-2,3-dihydrotabersonine	Kegg

Chemical Formula

C₂₂H₂₈N₂O₄

Average Mass

384.4760 Da

Monoisotopic Mass

384.20491 Da

IUPAC Name

methyl (1S,9R,10R,12R,19S)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

Traditional Name

methyl (1S,9R,10R,12R,19S)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@]12C[C@@](O)([C@@H]3NC4=CC(OC)=CC=C4[C@@]33CCN(CC=C1)[C@@H]23)C(=O)OC

InChI Identifier

InChI=1S/C22H28N2O4/c1-4-20-8-5-10-24-11-9-21(18(20)24)15-7-6-14(27-2)12-16(15)23-17(21)22(26,13-20)19(25)28-3/h5-8,12,17-18,23,26H,4,9-11,13H2,1-3H3/t17-,18+,20+,21+,22-/m1/s1

InChI Key

MLIQIRKAHMVCDD-MMGCJVFTSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Plumeran-type alkaloids

Sub Class

Not Available

Direct Parent

Plumeran-type alkaloids

Alternative Parents

Substituents

Plumeran-type alkaloid
Carbazole
Indole or derivatives
Dihydroindole
Anisole
Alkyl aryl ether
Aralkylamine
Secondary aliphatic/aromatic amine
N-alkylpyrrolidine
Benzenoid
Methyl ester
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:18430 )
organic heteropentacyclic compound (CHEBI:18430 )
methyl ester (CHEBI:18430 )
monoterpenoid indole alkaloid (CHEBI:18430 )
Indole alkaloids (C04578 )

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	1.73	ChemAxon
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.7 m³·mol⁻¹	ChemAxon
Polarizability	41.81 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

389344

KEGG Compound ID

C04578

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine

METLIN ID

Not Available

PubChem Compound

440391

PDB ID

Not Available

ChEBI ID

18430

Good Scents ID

Not Available

References

General References

Qu Y, Easson ML, Froese J, Simionescu R, Hudlicky T, De Luca V: Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. Proc Natl Acad Sci U S A. 2015 May 12;112(19):6224-9. doi: 10.1073/pnas.1501821112. Epub 2015 Apr 27. [PubMed:25918424 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate (NP0267743)

MOL for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

3D MOL for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

3D SDF for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

3D-SDF for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

PDB for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

3D PDB for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

SMILES for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

INCHI for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

Structure for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)

3D Structure for NP0267743 (methyl (1s,9r,10r,12r,19s)-12-ethyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate)