NP-MRD: Showing NP-Card for Tylocrebrine (NP0074305)

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Record Information

Version

2.0

Created at

2022-04-28 19:27:41 UTC

Updated at

2022-04-28 19:27:41 UTC

NP-MRD ID

NP0074305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tylocrebrine

Description

TYLOCREBRINE 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. Tylocrebrine is found in Ficus septica, Tylophora crebriflora and Tylophora floribunda. Tylocrebrine was first documented in 2005 (PMID: 16038551). Based on a literature review a small amount of articles have been published on TYLOCREBRINE (PMID: 26065924) (PMID: 24679059) (PMID: 21142214) (PMID: 20721818).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221272D          

 29 33  0  0  1  0            999 V2000
    3.9629    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689    2.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235    3.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    4.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    4.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    4.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7720    4.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  7 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -1.1508   -5.2573   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -4.3000   -0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8449   -2.9500   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -2.5592   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408   -1.2162   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -0.8115   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.5056   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    1.4463    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7933    2.7726    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1807    3.7372    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130    3.3934    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5035    4.3570    0.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131    5.7131    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9140    2.0435    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2819    1.8304    0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0214    2.0162   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.0994    0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637   -0.2574    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -0.6701    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517   -2.0448    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -2.3863    0.1773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2253   -1.4605    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262    1.0039   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228   -0.0356   -0.6627 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0989    0.2521   -0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -1.0446    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6374   -2.0597   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211   -1.2097    0.1021 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1246   -1.8515   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -6.2319   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4194   -5.0235   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -5.3856    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2740   -3.2686   -0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178    3.0925    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292    4.7739    0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145    6.3117    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    5.9900   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    5.8721    1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1955    3.0949   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4409    1.5365   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0136    1.5373   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3792   -0.0261    0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1778   -2.0292    0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0069   -0.8447    1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2631   -0.8340   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790    1.4995    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    1.7523   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305    0.5729   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1906    1.0519    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517   -1.2835   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8975   -0.9670    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969   -2.3342   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.9378    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.0241    1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997   -2.2692   -1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -2.6822    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 20  2  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 14  2  0
 14 15  1  0
 15 16  1  0
 14 11  1  0
 17  8  1  0
 23  7  1  0
 18  5  1  0
 24 28  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 10 35  1  0
  9 34  1  0
 29 55  1  0
 29 56  1  0
 28 54  1  1
 27 52  1  0
 27 53  1  0
 26 50  1  0
 26 51  1  0
 25 48  1  0
 25 49  1  0
 23 46  1  0
 23 47  1  0
  4 33  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
 16 39  1  0
 16 40  1  0
 16 41  1  0
M  END


  Mrv1652304282221272D          

 29 33  0  0  1  0            999 V2000
    3.9629    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689    2.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235    3.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    4.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    4.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    4.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7720    4.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  7 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C3=C(C[C@H]4CCCN4C3)C3=CC(OC)=C(OC)C=C3C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO4/c1-26-20-8-7-15-19-13-25-9-5-6-14(25)10-16(19)17-11-21(27-2)22(28-3)12-18(17)23(15)24(20)29-4/h7-8,11-12,14H,5-6,9-10,13H2,1-4H3/t14-/m1/s1

> <INCHI_KEY>
YFEPHJVWLFGWKH-CQSZACIVSA-N

> <FORMULA>
C24H27NO4

> <MOLECULAR_WEIGHT>
393.483

> <EXACT_MASS>
393.194008353

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.43643191788361

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20R)-4,5,9,10-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>
4.05

> <JCHEM_LOGP>
3.7683640766666664

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.737562078593653

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
113.87469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(20R)-4,5,9,10-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       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.874   0.406   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.896   3.938   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.380   3.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.652   3.125   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.129   4.573   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.221  -1.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.387   4.844   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.911   6.292   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.427   6.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.419   5.386   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.950   8.012   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.957   9.189   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.918   7.470   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.441   8.918   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   22                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21    7                                                       
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    1                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Tylocrebrine, (S)-isomer	MeSH

Chemical Formula

C₂₄H₂₇NO₄

Average Mass

393.4830 Da

Monoisotopic Mass

393.19401 Da

IUPAC Name

(20R)-4,5,9,10-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)-4,5,9,10-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=CC=C2C3=C(C[C@H]4CCCN4C3)C3=CC(OC)=C(OC)C=C3C2=C1OC

InChI Identifier

InChI=1S/C24H27NO4/c1-26-20-8-7-15-19-13-25-9-5-6-14(25)10-16(19)17-11-21(27-2)22(28-3)12-18(17)23(15)24(20)29-4/h7-8,11-12,14H,5-6,9-10,13H2,1-4H3/t14-/m1/s1

InChI Key

YFEPHJVWLFGWKH-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, 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
Ficus septica	Plant	KNApSAcK
Tylophora crebriflora	Plant	KNApSAcK
Tylophora floribunda	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

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	4.05	ALOGPS
logP	3.77	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	8.74	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	44.44 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

C00035194

Chemspider ID

216042

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

246845

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Damu AG, Kuo PC, Shi LS, Li CY, Kuoh CS, Wu PL, Wu TS: Phenanthroindolizidine alkaloids from the stems of Ficus septica. J Nat Prod. 2005 Jul;68(7):1071-5. doi: 10.1021/np050095o. [PubMed:16038551 ]
Kirtane AR, Wong HL, Guru BR, Lis LG, Georg GI, Gurvich VJ, Panyam J: Reformulating Tylocrebrine in Epidermal Growth Factor Receptor Targeted Polymeric Nanoparticles Improves Its Therapeutic Index. Mol Pharm. 2015 Aug 3;12(8):2912-23. doi: 10.1021/acs.molpharmaceut.5b00173. Epub 2015 Jul 3. [PubMed:26065924 ]
Zheng Y, Liu Y, Wang Q: Collective asymmetric synthesis of (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert-butanesulfinamide as a chiral auxiliary. J Org Chem. 2014 Apr 18;79(8):3348-57. doi: 10.1021/jo500013e. Epub 2014 Mar 28. [PubMed:24679059 ]
Niphakis MJ, Georg GI: Synthesis of tylocrebrine and related phenanthroindolizidines by VOF3-mediated oxidative aryl-alkene coupling. Org Lett. 2011 Jan 21;13(2):196-9. doi: 10.1021/ol1023954. Epub 2010 Dec 14. [PubMed:21142214 ]
Gater D: 32nd National Medicinal Chemistry Symposium--medicinal chemistry developments for cancer, and cardiovascular, metabolic and psychiatric disorders. IDrugs. 2010 Aug;13(8):517-9. [PubMed:20721818 ]

Showing NP-Card for Tylocrebrine (NP0074305)

MOL for NP0074305 (Tylocrebrine)

3D MOL for NP0074305 (Tylocrebrine)

3D SDF for NP0074305 (Tylocrebrine)

3D-SDF for NP0074305 (Tylocrebrine)

PDB for NP0074305 (Tylocrebrine)

3D PDB for NP0074305 (Tylocrebrine)

SMILES for NP0074305 (Tylocrebrine)

INCHI for NP0074305 (Tylocrebrine)

Structure for NP0074305 (Tylocrebrine)

3D Structure for NP0074305 (Tylocrebrine)