NP-MRD: Showing NP-Card for methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate (NP0216103)

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Record Information

Version

2.0

Created at

2022-09-05 15:56:27 UTC

Updated at

2022-09-05 15:56:27 UTC

NP-MRD ID

NP0216103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Description

Dihydrocorynantheine, also known as corynantheidine or hirsutine, belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate is found in Cephalanthus occidentalis, Corynanthe pachyceras, Uncaria cordata, Uncaria rhynchophylla, Uncaria sinensis and Uncaria tomentosa. methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate was first documented in 2011 (PMID: 21070010). Based on a literature review a small amount of articles have been published on Dihydrocorynantheine (PMID: 29268964) (PMID: 34854134) (PMID: 25306115) (PMID: 22052788).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217562D          

 27 30  0  0  1  0            999 V2000
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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  2  0  0  0  0
  9 10  1  0  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  2  0  0  0  0
  8 16  1  0  0  0  0
 11 16  1  0  0  0  0
 17  9  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -3.7192   -1.8366    1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4065   -2.3923    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -1.4076    0.7656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0749   -2.2611    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -1.4878    0.3065 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874   -2.3014    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -1.8028   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4409   -0.3157   -0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    0.3429   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    1.6702   -0.6538 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    1.8957   -0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5558    3.0207   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9391    2.9626   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5239    1.7159   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626    0.5521   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4014    0.6540   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159   -0.5095   -0.7623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1625    0.3812   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -0.4011   -0.3204 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5529    0.5684   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194    0.6341   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665   -0.1665   -2.1543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024   -0.7357   -2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405    1.4745    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339    1.4241    1.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6524    2.3836    1.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026    3.2538    2.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4223   -1.6175    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762   -1.0316    2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -2.6529    1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -3.1156    1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937   -3.0568    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -0.9370    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3314   -2.6769   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -3.1063    1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7305   -2.3151    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1037   -3.3650    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -2.2016   -0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171   -2.1450   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232    2.4446   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460    3.9838   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5341    3.8671   -0.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004    1.6623   -0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2208   -0.4283   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -0.9771   -1.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562    0.8415    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2475    1.2024   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5611   -0.9448   -1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226    1.3431   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6820   -1.3413   -3.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2572   -1.3460   -1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5540    0.0615   -2.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4905    2.7259    3.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192    3.7170    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    4.0936    2.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 19  3  1  0
 17  5  1  0
 16  8  1  0
 16 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  1
  4 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
 10 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  6
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
M  END


  Mrv1652309052217562D          

 27 30  0  0  1  0            999 V2000
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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  2  0  0  0  0
  9 10  1  0  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  2  0  0  0  0
  8 16  1  0  0  0  0
 11 16  1  0  0  0  0
 17  9  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CCC3=C(NC4=CC=CC=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14?,17-,20-/m0/s1

> <INCHI_KEY>
NMLUOJBSAYAYEM-VXQWDRHASA-N

> <FORMULA>
C22H28N2O3

> <MOLECULAR_WEIGHT>
368.477

> <EXACT_MASS>
368.20999277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.15307633788878

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2S,12bS)-3-ethyl-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_LOGP>
3.457264852333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.37471338388541

> <JCHEM_PKA_STRONGEST_BASIC>
7.287975188601867

> <JCHEM_POLAR_SURFACE_AREA>
54.56

> <JCHEM_REFRACTIVITY>
106.44999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,12bS)-3-ethyl-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.228  -6.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.921  -5.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.303  -6.305   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.841  -6.217   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.076  -3.818   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.462  -3.906   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.153   0.309   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.536  -0.891   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.381  -2.178   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   11                                                  
CONECT   17    9    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    3   20                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Corynantheidine	MeSH
Hirsutine	MeSH
Hirsutine, (16E)-isomer	MeSH
Hirsutine, (3beta,16E)-isomer	MeSH
18,19-Dihydrocorynantheine	MeSH
Hirsutine, (16E,20beta)-isomer	MeSH

Chemical Formula

C₂₂H₂₈N₂O₃

Average Mass

368.4770 Da

Monoisotopic Mass

368.20999 Da

IUPAC Name

methyl (2E)-2-[(2S,12bS)-3-ethyl-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2S,12bS)-3-ethyl-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

CCC1CN2CCC3=C(NC4=CC=CC=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

InChI Identifier

InChI=1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14?,17-,20-/m0/s1

InChI Key

NMLUOJBSAYAYEM-VXQWDRHASA-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
Cephalanthus occidentalis	LOTUS Database	35616633
Corynanthe pachyceras	LOTUS Database	35616633
Uncaria cordata	LOTUS Database	35616633
Uncaria rhynchophylla	LOTUS Database	35616633
Uncaria sinensis	LOTUS Database	35616633
Uncaria tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
Quinolizine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Vinylogous ester
Pyrrole
Methyl ester
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Amine
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic nitrogen 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	3.46	ChemAxon
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	7.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.45 m³·mol⁻¹	ChemAxon
Polarizability	42.15 Å³	ChemAxon
Number of Rings	4	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

C00025166

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

101287817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gutierrez-Rebolledo GA, Drier-Jonas S, Jimenez-Arellanes MA: Natural compounds and extracts from Mexican medicinal plants with anti-leishmaniasis activity: An update. Asian Pac J Trop Med. 2017 Dec;10(12):1105-1110. doi: 10.1016/j.apjtm.2017.10.016. Epub 2017 Nov 7. [PubMed:29268964 ]
Wang K, Zhou XY, Wang YY, Li MM, Li YS, Peng LY, Cheng X, Li Y, Wang YP, Zhao QS: Macrophyllionium and macrophyllines A and B, oxindole alkaloids from Uncaria macrophylla. J Nat Prod. 2011 Jan 28;74(1):12-5. doi: 10.1021/np1004938. Epub 2010 Nov 11. [PubMed:21070010 ]
Sakamoto J, Ishikawa H: Bioinspired Transformations Using Strictosidine Aglycones: Divergent Total Syntheses of Monoterpenoid Indole Alkaloids in the Early Stage of Biosynthesis. Chemistry. 2022 Feb 21;28(10):e202104052. doi: 10.1002/chem.202104052. Epub 2021 Dec 21. [PubMed:34854134 ]
Gai Y, Chen H, Liu W, Feng F, Xie N: The metabolism of YiGan San and subsequent pharmacokinetic evaluation of four metabolites in rat based on liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Dec 1;972:22-8. doi: 10.1016/j.jchromb.2014.09.033. Epub 2014 Sep 30. [PubMed:25306115 ]
Zhang W, Bah J, Wohlfarth A, Franzen J: A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related natural and nonnatural compounds. Chemistry. 2011 Dec 2;17(49):13814-24. doi: 10.1002/chem.201102012. Epub 2011 Nov 3. [PubMed:22052788 ]
LOTUS database [Link]

Showing NP-Card for methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate (NP0216103)

MOL for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D MOL for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D SDF for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D-SDF for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

PDB for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D PDB for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

SMILES for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

INCHI for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

Structure for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D Structure for NP0216103 (methyl (2e)-2-[(2s,12bs)-3-ethyl-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)