NP-MRD: Showing NP-Card for (-)-tylophorine (NP0153324)

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Record Information

Version

2.0

Created at

2022-09-02 09:57:29 UTC

Updated at

2022-09-02 09:57:29 UTC

NP-MRD ID

NP0153324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-tylophorine

Description

Tylophorine, (-)-, also known as dehydrotylophorine, 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 Vincetoxicum hirundinaria and Ficus septica. (-)-tylophorine was first documented in 2021 (PMID: 34745429). Based on a literature review a small amount of articles have been published on Tylophorine, (-)- (PMID: 35631719) (PMID: 34917259) (PMID: 34913151) (PMID: 35890406).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211572D          

 29 33  0  0  1  0            999 V2000
    5.0884   -4.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763   -4.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  3 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 24  1  1  0  0  0
 28 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -3.6640    4.0655   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2985    4.3922   -0.6533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685    3.3591   -0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    2.0729   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8530    1.0461   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2814   -0.2421    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368   -1.2070    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -0.9146    0.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618   -1.9148    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3104   -1.6373    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2468   -2.6375    0.7856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773   -3.9515    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6969   -0.3200    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0419   -0.0733    0.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5062    1.2445    0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    0.7037    0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449    0.3958    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031    1.3974   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967    2.7002   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0486    3.7134   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723    5.0169   -0.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7543    5.2858   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284   -2.5890    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878   -2.9197    0.5597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679   -3.8581   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040   -3.1909   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -2.4214   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.9182    0.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6983   -0.5546    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    3.2033   -1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    4.9278   -0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9748    3.8004    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8058    1.8078   -0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -2.9277    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814   -4.2651    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116   -4.0378    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6344   -4.6684    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6183    1.3055    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408    1.5709   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0694    1.9605    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    1.6730   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    3.0136   -0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2194    4.6389   -1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9874    6.3211   -0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410    5.0167    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -3.2218   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439   -2.8837    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -4.7505    0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6233   -4.1267   -1.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564   -3.9584   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.4988   -1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8469   -3.1455    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8846   -1.5924   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3792   -1.8930    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0783   -0.4735   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2942    0.1606    0.8728 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  1
 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


  Mrv1652309022211572D          

 29 33  0  0  1  0            999 V2000
    5.0884   -4.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763   -4.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  3 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 24  1  1  0  0  0
 28 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153324

> <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-/m1/s1

> <INCHI_KEY>
SSEUDFYBEOIWGF-CQSZACIVSA-N

> <FORMULA>
C24H27NO4

> <MOLECULAR_WEIGHT>
393.483

> <EXACT_MASS>
393.194008353

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.943239141274816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20R)-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>
113.87469999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(20R)-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.498  -9.091   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.982  -8.820   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.459  -7.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943  -7.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.904  -5.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.381  -3.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.374  -2.755   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -1.307   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.843  -0.129   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.320   1.319   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.804   1.590   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.359  -0.400   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.352   0.777   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.868   0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.882  -1.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -3.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.413  -4.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.929  -4.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.452  -6.194   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.968  -6.465   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.491  -7.913   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.865  -3.661   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.872  -4.839   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -0.667  -4.889   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.095  -6.368   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.179  -7.232   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.395  -6.287   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.911  -6.558   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    7   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28    6                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₄H₂₇NO₄

Average Mass

393.4830 Da

Monoisotopic Mass

393.19401 Da

IUPAC Name

(20R)-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

(20R)-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-/m1/s1

InChI Key

SSEUDFYBEOIWGF-CQSZACIVSA-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
Cynanchum vincetoxicum	LOTUS Database	35616633
Ficus septica	LOTUS Database	35616633

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
Phenol ether
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
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	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	44.94 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

9058995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10883727

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Mostafa EM, Mohammed HA, Musa A, Abdelgawad MA, Al-Sanea MM, Almahmoud SA, Ghoneim MM, Gomaa HAM, Rahman FESA, Shalaby K, Selim S, Khan RA: In Vitro Anti-Proliferative, and Kinase Inhibitory Activity of Phenanthroindolizidine Alkaloids Isolated from Tylophora indica. Plants (Basel). 2022 May 12;11(10). pii: plants11101295. doi: 10.3390/plants11101295. [PubMed:35631719 ]
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 ]
Lee YZ, Hsu HY, Yang CW, Lin YL, Chang SY, Yang RB, Liang JJ, Chao TL, Liao CC, Kao HC, Chang JY, Sytwu HK, Chen CT, Lee SJ: The Synergistic Inhibition of Coronavirus Replication and Induced Cytokine Production by Ciclesonide and the Tylophorine-Based Compound Dbq33b. Pharmaceutics. 2022 Jul 21;14(7):1511. doi: 10.3390/pharmaceutics14071511. [PubMed:35890406 ]
LOTUS database [Link]

Showing NP-Card for (-)-tylophorine (NP0153324)

MOL for NP0153324 ((-)-tylophorine)

3D MOL for NP0153324 ((-)-tylophorine)

3D SDF for NP0153324 ((-)-tylophorine)

3D-SDF for NP0153324 ((-)-tylophorine)

PDB for NP0153324 ((-)-tylophorine)

3D PDB for NP0153324 ((-)-tylophorine)

SMILES for NP0153324 ((-)-tylophorine)

INCHI for NP0153324 ((-)-tylophorine)

Structure for NP0153324 ((-)-tylophorine)

3D Structure for NP0153324 ((-)-tylophorine)