NP-MRD: Showing NP-Card for Paynantheine (NP0331714)

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Record Information

Version

2.0

Created at

2023-07-13 15:43:31 UTC

Updated at

2024-09-03 04:16:36 UTC

NP-MRD ID

NP0331714

Natural Product DOI

https://doi.org/10.57994/0730

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paynantheine

Description

Paynantheine 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. Paynantheine was first documented in 2020 (PMID: 32597657). Based on a literature review a significant number of articles have been published on Paynantheine (PMID: 33620222) (PMID: 35472200) (PMID: 35468648) (PMID: 33408731) (PMID: 35335999) (PMID: 34803709).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214182D          

 29 32  0  0  1  0            999 V2000
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985    3.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 12 10  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 13 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
 12 19  1  0  0  0  0
 18 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
 17 28  1  6  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.6927    2.9825    1.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9606    2.8402    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138    1.5716   -0.3213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0695    1.4765   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1967    1.0549    1.1178 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3904    1.5832    1.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    1.1911    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.1958    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463   -0.9262    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123   -2.1267   -0.0896 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8762   -2.1576   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343   -3.1263   -1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492   -2.8822   -1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5462   -1.6907   -1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871   -0.7312   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431    0.5088   -0.2587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    0.8805   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -0.9510   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.3883    1.1528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1243   -0.7774    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574    0.3480    0.3160 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3313   -0.2113   -0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4669   -0.3365    0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    0.0183    1.5843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9849    0.4173    1.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2462   -0.6305   -1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1823   -0.5297   -2.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3499   -1.1542   -2.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3574   -1.5747   -3.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    4.0185    1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708    2.2321    1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520    3.7467   -0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174    1.6091   -1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    2.4185   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147    0.7076   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671    1.1903    2.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906    2.6743    1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811    1.1411    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452    1.9051    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9089   -2.8869   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1494   -4.0505   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5169   -3.6460   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5673   -1.4267   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6913    2.0065   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3790    0.5499    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0242    0.5613   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672   -0.7043    2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -1.6059    0.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8801   -1.1662   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    0.5407    1.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3017   -0.7601   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3213    1.3013    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0013    0.6169    3.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7344   -0.3926    1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8075   -2.5248   -3.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -0.7461   -4.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4185   -1.7925   -4.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19  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  1  0
 16 17  1  0
 15 18  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
  3 21  1  0
  9 19  1  0
 18 11  1  0
 18  8  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 23 51  1  0
 21 50  1  1
 20 48  1  0
 20 49  1  0
 19 47  1  1
  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
 17 44  1  0
 17 45  1  0
 17 46  1  0
  4 34  1  0
  4 35  1  0
  3 33  1  6
  2 32  1  0
  1 30  1  0
  1 31  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
M  END


  Mrv1652304282214182D          

 29 32  0  0  1  0            999 V2000
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985    3.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 12 10  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 13 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
 12 19  1  0  0  0  0
 18 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
 17 28  1  6  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331714

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C=C(/[C@H]1C[C@@H]2N(CCC3=C2NC2=CC=CC(OC)=C32)C[C@@H]1C=C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19-/m0/s1

> <INCHI_KEY>
JGZKIGWXPPFMRG-CYSPOEIOSA-N

> <FORMULA>
C23H28N2O4

> <MOLECULAR_WEIGHT>
396.487

> <EXACT_MASS>
396.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.53985555169956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2S,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.995605600333334

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.670265610387272

> <JCHEM_PKA_STRONGEST_BASIC>
6.898711484113814

> <JCHEM_POLAR_SURFACE_AREA>
63.78999999999999

> <JCHEM_REFRACTIVITY>
112.95729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.962  -2.307   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.593  -3.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.372   2.147   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.179  -0.517   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.024  -1.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.356   3.345   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.894   3.257   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.586   1.881   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.124   1.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.336   4.720   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.874   4.809   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.509   6.008   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.184   7.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.741   0.594   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.434  -0.782   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   12                                                       
CONECT   20   18   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                                                            
CONECT   28   17   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈N₂O₄

Average Mass

396.4870 Da

Monoisotopic Mass

396.20491 Da

IUPAC Name

methyl (2E)-2-[(2S,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2S,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

CO\C=C(/[C@H]1C[C@@H]2N(CCC3=C2NC2=CC=CC(OC)=C32)C[C@@H]1C=C)C(=O)OC

InChI Identifier

InChI=1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19-/m0/s1

InChI Key

JGZKIGWXPPFMRG-CYSPOEIOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
speciosa		Not Available

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
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Pyrrole
Enoate ester
Methyl ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.18	ALOGPS
logP	3	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.96 m³·mol⁻¹	ChemAxon
Polarizability	44.54 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025182

Chemspider ID

2301316

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3037629

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kamble SH, Berthold EC, King TI, Raju Kanumuri SR, Popa R, Herting JR, Leon F, Sharma A, McMahon LR, Avery BA, McCurdy CR: Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. J Nat Prod. 2021 Apr 23;84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. Epub 2021 Feb 23. [PubMed:33620222 ]
Flores-Bocanegra L, Raja HA, Graf TN, Augustinovic M, Wallace ED, Hematian S, Kellogg JJ, Todd DA, Cech NB, Oberlies NH: The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids. J Nat Prod. 2020 Jul 24;83(7):2165-2177. doi: 10.1021/acs.jnatprod.0c00257. Epub 2020 Jun 29. [PubMed:32597657 ]
Zhang M, Sharma A, Leon F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ: Plant growth and phytoactive alkaloid synthesis in kratom [Mitragyna speciosa (Korth.)] in response to varying radiance. PLoS One. 2022 Apr 26;17(4):e0259326. doi: 10.1371/journal.pone.0259326. eCollection 2022. [PubMed:35472200 ]
Manwill PK, Flores-Bocanegra L, Khin M, Raja HA, Cech NB, Oberlies NH, Todd DA: Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products. Planta Med. 2022 Apr 25. doi: 10.1055/a-1795-5876. [PubMed:35468648 ]
Zhang M, Sharma A, Leon F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ: Effects of Nutrient Fertility on Growth and Alkaloidal Content in Mitragyna speciosa (Kratom). Front Plant Sci. 2020 Dec 21;11:597696. doi: 10.3389/fpls.2020.597696. eCollection 2020. [PubMed:33408731 ]
Tanna RS, Nguyen JT, Hadi DL, Manwill PK, Flores-Bocanegra L, Layton ME, White JR, Cech NB, Oberlies NH, Rettie AE, Thummel KE, Paine MF: Clinical Pharmacokinetic Assessment of Kratom (Mitragyna speciosa), a Botanical Product with Opioid-like Effects, in Healthy Adult Participants. Pharmaceutics. 2022 Mar 11;14(3). pii: pharmaceutics14030620. doi: 10.3390/pharmaceutics14030620. [PubMed:35335999 ]
Gutridge AM, Chakraborty S, Varga BR, Rhoda ES, French AR, Blaine AT, Royer QH, Cui H, Yuan J, Cassell RJ, Szabo M, Majumdar S, van Rijn RM: Evaluation of Kratom Opioid Derivatives as Potential Treatment Option for Alcohol Use Disorder. Front Pharmacol. 2021 Nov 3;12:764885. doi: 10.3389/fphar.2021.764885. eCollection 2021. [PubMed:34803709 ]
Leon F, Obeng S, Mottinelli M, Chen Y, King TI, Berthold EC, Kamble SH, Restrepo LF, Patel A, Gamez-Jimenez LR, Lopera-Londono C, Hiranita T, Sharma A, Hampson AJ, Canal CE, McMahon LR, McCurdy CR: Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors. J Med Chem. 2021 Sep 23;64(18):13510-13523. doi: 10.1021/acs.jmedchem.1c00726. Epub 2021 Sep 1. [PubMed:34467758 ]
Teh JL, Abdul Rahman SF, Domnic G, Satiyasilan L, Chear NJY, Singh D, Mohana-Kumaran N: Rapid spheroid assays in a 3-dimensional cell culture chip. BMC Res Notes. 2021 Aug 13;14(1):310. doi: 10.1186/s13104-021-05727-0. [PubMed:34389056 ]
Domnic G, Jeng-Yeou Chear N, Abdul Rahman SF, Ramanathan S, Lo KW, Singh D, Mohana-Kumaran N: Combinations of indole based alkaloids from Mitragyna speciosa (Kratom) and cisplatin inhibit cell proliferation and migration of nasopharyngeal carcinoma cell lines. J Ethnopharmacol. 2021 Oct 28;279:114391. doi: 10.1016/j.jep.2021.114391. Epub 2021 Jul 2. [PubMed:34224811 ]
Goh YS, Karunakaran T, Murugaiyah V, Santhanam R, Abu Bakar MH, Ramanathan S: Accelerated Solvent Extractions (ASE) of Mitragyna speciosa Korth. (Kratom) Leaves: Evaluation of Its Cytotoxicity and Antinociceptive Activity. Molecules. 2021 Jun 17;26(12). pii: molecules26123704. doi: 10.3390/molecules26123704. [PubMed:34204457 ]
Kamble SH, Sharma A, King TI, Berthold EC, Leon F, Meyer PKL, Kanumuri SRR, McMahon LR, McCurdy CR, Avery BA: Exploration of cytochrome P450 inhibition mediated drug-drug interaction potential of kratom alkaloids. Toxicol Lett. 2020 Feb 1;319:148-154. doi: 10.1016/j.toxlet.2019.11.005. Epub 2019 Nov 7. [PubMed:31707106 ]
Lee MJ, Ramanathan S, Mansor SM, Tan SC: Development of an ELISA for detection of mitragynine and its metabolites in human urine. Anal Biochem. 2020 Jun 15;599:113733. doi: 10.1016/j.ab.2020.113733. Epub 2020 Apr 14. [PubMed:32302607 ]
Basiliere S, Kerrigan S: Temperature and pH-Dependent Stability of Mitragyna Alkaloids. J Anal Toxicol. 2020 May 18;44(4):314-324. doi: 10.1093/jat/bkz103. [PubMed:31897484 ]
Singh D, Yeou Chear NJ, Narayanan S, Leon F, Sharma A, McCurdy CR, Avery BA, Balasingam V: Patterns and reasons for kratom (Mitragyna speciosa) use among current and former opioid poly-drug users. J Ethnopharmacol. 2020 Mar 1;249:112462. doi: 10.1016/j.jep.2019.112462. Epub 2019 Dec 7. [PubMed:31816368 ]

Showing NP-Card for Paynantheine (NP0331714)

MOL for NP0331714 (Paynantheine)

3D MOL for NP0331714 (Paynantheine)

3D SDF for NP0331714 (Paynantheine)

3D-SDF for NP0331714 (Paynantheine)

PDB for NP0331714 (Paynantheine)

3D PDB for NP0331714 (Paynantheine)

SMILES for NP0331714 (Paynantheine)

INCHI for NP0331714 (Paynantheine)

Structure for NP0331714 (Paynantheine)

3D Structure for NP0331714 (Paynantheine)