NP-MRD: Showing NP-Card for Tylophorine (NP0051384)

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Record Information

Version

2.0

Created at

2022-04-27 22:46:20 UTC

Updated at

2022-04-27 22:46:20 UTC

NP-MRD ID

NP0051384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tylophorine

Description

Tylophorine belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene. Tylophorine is found in Cynanchum vincetoxicum, Ficus septica, Pergularia pallida, Tylophora asthmatica , Tylophora crebriflora, Tylophora floribunda, Tylophora tanakae and Vincetoxicum hirundinara. Tylophorine was first documented in 2021 (PMID: 34206005). Based on a literature review a small amount of articles have been published on Tylophorine (PMID: 34745429) (PMID: 34917259) (PMID: 34913151) (PMID: 34210137).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200462D          

 29 33  0  0  1  0            999 V2000
    4.9691   -0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767   -1.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -0.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1540    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5585    3.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706    3.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -2.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282   -2.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2206   -2.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
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  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
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 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
  8 18  2  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
  7 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -1.4759   -5.4305   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -4.3600   -0.1226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0407   -3.0291   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -2.6430   -0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -1.3014   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416   -0.9578   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2555    0.3872   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033    1.3770   -0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    2.6993   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239    3.7014    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035    4.9690    0.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3063    6.1936    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6338    3.2999    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5930    4.2652    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    3.8927    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9873    1.9529    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321    0.9698   -0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3962   -0.3732   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -0.7442    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0396   -2.0843    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3236   -2.5181    0.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5048   -1.7847    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    0.7184   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110   -0.2808    0.3614 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015   -0.0297    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4027   -1.3946    0.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3390   -2.3759    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -1.4868   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9455   -2.0391   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872   -5.4507   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742   -6.3810   -0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -5.4250    0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -3.3788   -0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886    2.9901   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4018    6.4322    0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172    6.8793   -0.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    6.7420    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2337    3.4143    1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012    3.1846   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093    4.7877    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0209    1.6655    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5298   -0.0663    0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -1.4515   -0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3068   -2.3359    0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3613   -0.8500    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183    1.7141   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9481    0.4977   -1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873    0.3374   -0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505    0.6750    1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3532   -1.5245    0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5325   -1.5447    1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822   -2.9436    1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8210   -3.0276   -0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459   -1.2498   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -2.7626    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958   -2.5214   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  2  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 18  2  0
 18  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
  4  3  1  0
 29  6  1  0
 17  8  1  0
 17 18  1  0
 28 24  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 19 42  1  0
  4 33  1  0
 23 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 27 53  1  0
 28 54  1  6
 29 55  1  0
 29 56  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
M  END


  Mrv1652304282200462D          

 29 33  0  0  1  0            999 V2000
    4.9691   -0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767   -1.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -0.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1540    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5585    3.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706    3.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -2.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282   -2.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2206   -2.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  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
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
  8 18  2  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
  7 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(=C1)C1=C(CN3CCC[C@H]3C1)C1=CC(OC)=C(OC)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO4/c1-26-21-9-16-15-8-14-6-5-7-25(14)13-20(15)19-12-24(29-4)23(28-3)11-18(19)17(16)10-22(21)27-2/h9-12,14H,5-8,13H2,1-4H3/t14-/m0/s1

> <INCHI_KEY>
SSEUDFYBEOIWGF-AWEZNQCLSA-N

> <FORMULA>
C24H27NO4

> <MOLECULAR_WEIGHT>
393.483

> <EXACT_MASS>
393.194008353

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.873926525347485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20S)-4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
3.7683640766666664

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.66607909494835

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
113.87469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(20S)-4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene

> <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       9.276  -1.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.752  -2.680   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.237  -2.951   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.244  -1.773   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.767  -0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.283  -0.054   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.806   1.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.813   2.572   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.297   2.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.774   0.852   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.258   0.581   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.266   1.759   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.789   3.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.305   3.478   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.573   4.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.298   3.288   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.726   1.809   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.337   4.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.853   4.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.845   3.114   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.322   1.666   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.361   3.385   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.354   2.208   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.376   5.740   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.892   6.011   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.713  -4.399   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.706  -5.576   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.745  -3.857   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.222  -5.305   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    8   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20    7                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19   25                                                       
CONECT   25   24                                                            
CONECT   26    3   27                                                       
CONECT   27   26                                                            
CONECT   28    2   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
2,3,6,7-Tetramethoxyphenanthro(9,10:6,7')indolizidine	MeSH
Dehydrotylophorine	MeSH

Chemical Formula

C₂₄H₂₇NO₄

Average Mass

393.4830 Da

Monoisotopic Mass

393.19401 Da

IUPAC Name

(20S)-4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene

Traditional Name

(20S)-4,5,10,11-tetramethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(=C1)C1=C(CN3CCC[C@H]3C1)C1=CC(OC)=C(OC)C=C21

InChI Identifier

InChI=1S/C24H27NO4/c1-26-21-9-16-15-8-14-6-5-7-25(14)13-20(15)19-12-24(29-4)23(28-3)11-18(19)17(16)10-22(21)27-2/h9-12,14H,5-8,13H2,1-4H3/t14-/m0/s1

InChI Key

SSEUDFYBEOIWGF-AWEZNQCLSA-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, 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
Cynanchum vincetoxicum	Plant	KNApSAcK
Ficus septica	Plant	KNApSAcK
Pergularia pallida	Plant	KNApSAcK
Tylophora asthmatica	Plant	KNApSAcK
Tylophora crebriflora	Plant	KNApSAcK
Tylophora floribunda	Plant	KNApSAcK
Tylophora tanakae	Plant	KNApSAcK
Vincetoxicum hirundinara	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthroindolizidines

Direct Parent

Phenanthroindolizidines

Alternative Parents

Substituents

Phenanthroindolizidine
Naphthalene
Tetrahydroisoquinoline
Indolizidine
Anisole
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:9786 )
organonitrogen heterocyclic compound (CHEBI:9786 )

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	4.1	ALOGPS
logP	3.77	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.87 m³·mol⁻¹	ChemAxon
Polarizability	44.87 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

C00002367

Chemspider ID

83161

KEGG Compound ID

C10623

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92114

PDB ID

Not Available

ChEBI ID

9786

Good Scents ID

Not Available

References

General References

Omran Z, Guise CP, Chen L, Rauch C, Abdalla AN, Abdullah O, Sindi IA, Fischer PM, Smaill JB, Patterson AV, Liu Y, Wang Q: Design, Synthesis and In-Vitro Biological Evaluation of Antofine and Tylophorine Prodrugs as Hypoxia-Targeted Anticancer Agents. Molecules. 2021 Jun 1;26(11). pii: molecules26113327. doi: 10.3390/molecules26113327. [PubMed:34206005 ]
Wang Z, Ye F, Feng Y, Xiao W, Song H, Zhao L, Lu R, Huang B, Liu Y, Wang W, Li Y, Ding Y, Zheng Y, Song X, Tan W, Wang Q: Discovery and Nanosized Preparations of (S,R)-Tylophorine Malate as Novel anti-SARS-CoV-2 Agents. ACS Med Chem Lett. 2021 Oct 24;12(11):1838-1844. doi: 10.1021/acsmedchemlett.1c00481. eCollection 2021 Nov 11. [PubMed:34745429 ]
Xie L, Goto M, Chen X, Morris-Natschke SL, Lee KH: Lead Optimization: Synthesis and Biological Evaluation of PBT-1 Derivatives as Novel Antitumor Agents. ACS Med Chem Lett. 2021 Nov 17;12(12):1948-1954. doi: 10.1021/acsmedchemlett.1c00505. eCollection 2021 Dec 9. [PubMed:34917259 ]
Hossain R, Sarkar C, Hassan SMH, Khan RA, Arman M, Ray P, Islam MT, Dastan SD, Sharifi-Rad J, Almarhoon ZM, Martorell M, Setzer WN, Calina D: In Silico Screening of Natural Products as Potential Inhibitors of SARS-CoV-2 Using Molecular Docking Simulation. Chin J Integr Med. 2022 Mar;28(3):249-256. doi: 10.1007/s11655-021-3504-5. Epub 2021 Dec 15. [PubMed:34913151 ]
Yan C, Dong J, Liu Y, Li Y, Wang Q: Target-Directed Design, Synthesis, Antiviral Activity, and SARs of 9-Substituted Phenanthroindolizidine Alkaloid Derivatives. J Agric Food Chem. 2021 Jul 14;69(27):7565-7571. doi: 10.1021/acs.jafc.1c02276. Epub 2021 Jul 1. [PubMed:34210137 ]

Showing NP-Card for Tylophorine (NP0051384)

MOL for NP0051384 (Tylophorine)

3D MOL for NP0051384 (Tylophorine)

3D SDF for NP0051384 (Tylophorine)

3D-SDF for NP0051384 (Tylophorine)

PDB for NP0051384 (Tylophorine)

3D PDB for NP0051384 (Tylophorine)

SMILES for NP0051384 (Tylophorine)

INCHI for NP0051384 (Tylophorine)

Structure for NP0051384 (Tylophorine)

3D Structure for NP0051384 (Tylophorine)