NP-MRD: Showing NP-Card for Tuboxenine (NP0066950)

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Record Information

Version

2.0

Created at

2022-04-28 11:10:03 UTC

Updated at

2022-04-28 11:10:03 UTC

NP-MRD ID

NP0066950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tuboxenine

Description

Tuboxenine belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. Tuboxenine is found in Hunteria zeylanica , Pleiocarpa pycnantha and Pleiocarpa tubicina. Based on a literature review very few articles have been published on Tuboxenine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 50  0  0  0  0  0  0  0  0999 V2000
   -0.2370   -1.8614    1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8586   -1.5942    0.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6454   -0.2701    0.0451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7582   -0.1651    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    1.2225    1.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1292    2.2457    0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7595    2.0030    0.3319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    2.4646   -0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619    1.3192   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.2351   -0.5457 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9034   -0.0311   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7497    0.7556    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900    0.2975    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022   -0.9781    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5352   -1.7492    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2932   -1.3060   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -1.9231   -1.1359 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214   -1.1244   -1.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8704   -1.0753   -2.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614   -0.2423   -1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    0.6218    0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2767   -2.9737    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871   -1.5590    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -1.4310    2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -2.3974   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.1291    0.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -0.9125    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5845    1.5366    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8652    1.1168    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7925    2.3511   -0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1887    3.2268    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    3.3364   -0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026    2.8583   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898    1.1338   -2.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208    1.6949   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4453    1.7762    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637    0.9076    1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3774   -1.3172    1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891   -2.7566   -0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -2.8011   -1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2292   -2.1220   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544   -0.6788   -3.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032   -0.8038   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0801    0.7308   -1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495    0.3685    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  1  6
 20 19  1  0
 19 18  1  0
 18 17  1  6
 17 16  1  0
 16 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 11 10  1  0
 10  9  1  6
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  7 21  1  0
 18  2  1  0
 10 18  1  0
 21 10  1  0
  4  3  1  0
 21  3  1  0
 15 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
 20 43  1  0
 20 44  1  0
 19 41  1  0
 19 42  1  0
 17 40  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
  9 34  1  0
  9 35  1  0
  8 32  1  0
  8 33  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
  4 26  1  0
  4 27  1  0
 21 45  1  1
M  END


  Mrv1652304282213102D          

 21 26  0  0  1  0            999 V2000
    5.4931    1.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355    0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3129    0.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477    1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0280    1.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0009    0.8498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9003   -0.0199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7510   -0.2394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272   -0.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570   -0.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038    0.2460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1917    0.9778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9807    1.7782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726    1.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344    1.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064    0.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821    2.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2908    1.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -0.2849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5812   -1.0296    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
  7  4  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 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
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 12 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@]23CC[C@]11NC4=C(C=CC=C4)[C@@]11CCN(CCC2)[C@@H]31

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2/c1-13-17-7-4-11-21-12-10-18(16(17)21)14-5-2-3-6-15(14)20-19(13,18)9-8-17/h2-3,5-6,13,16,20H,4,7-12H2,1H3/t13-,16-,17-,18+,19-/m0/s1

> <INCHI_KEY>
ZMNQOAJDBCBZSX-FLTXXLLZSA-N

> <FORMULA>
C19H24N2

> <MOLECULAR_WEIGHT>
280.415

> <EXACT_MASS>
280.193948781

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5827531992731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9S,12S,19S,20S)-20-methyl-8,16-diazahexacyclo[10.6.1.1^{9,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2(7),3,5-triene

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
2.682447007666666

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.788520379618106

> <JCHEM_PKA_STRONGEST_BASIC>
10.59954488851929

> <JCHEM_POLAR_SURFACE_AREA>
15.27

> <JCHEM_REFRACTIVITY>
86.05210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,12S,19S,20S)-20-methyl-8,16-diazahexacyclo[10.6.1.1^{9,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2(7),3,5-triene

> <JCHEM_VEBER_RULE>
1

$$$$

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      10.254   2.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.586   0.809   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.051   0.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.182   1.965   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.850   3.353   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.386   3.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.602   1.586   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.414  -0.037   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.002  -0.447   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.277  -1.556   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.653  -1.520   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.181   0.459   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.091   1.825   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.697   3.319   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.189   3.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.184   2.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.692   0.913   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.007   4.178   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.143   3.144   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.614  -0.532   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.952  -1.922   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   13   19                                             
CONECT    8    7    9   10   20                                             
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17   20                                             
CONECT   13   12    7   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   14   19                                                       
CONECT   19   18    7                                                       
CONECT   20   12    8   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄N₂

Average Mass

280.4150 Da

Monoisotopic Mass

280.19395 Da

IUPAC Name

(1R,9S,12S,19S,20S)-20-methyl-8,16-diazahexacyclo[10.6.1.1^{9,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2(7),3,5-triene

Traditional Name

(1R,9S,12S,19S,20S)-20-methyl-8,16-diazahexacyclo[10.6.1.1^{9,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2(7),3,5-triene

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@]23CC[C@]11NC4=C(C=CC=C4)[C@@]11CCN(CCC2)[C@@H]31

InChI Identifier

InChI=1S/C19H24N2/c1-13-17-7-4-11-21-12-10-18(16(17)21)14-5-2-3-6-15(14)20-19(13,18)9-8-17/h2-3,5-6,13,16,20H,4,7-12H2,1H3/t13-,16-,17-,18+,19-/m0/s1

InChI Key

ZMNQOAJDBCBZSX-FLTXXLLZSA-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
Hunteria zeylanica	Plant	KNApSAcK
Pleiocarpa pycnantha	LOTUS Database	35616633
Pleiocarpa tubicina	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Carbazole
2,3-cyclopentanoindoline
Aromatic monoterpenoid
Norbornane monoterpenoid
Azaspirodecane
Quinolidine
Monoterpenoid
Indole or derivatives
Dihydroindole
Indolizidine
Aralkylamine
Secondary aliphatic/aromatic amine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Secondary amine
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic nitrogen compound
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	3.71	ALOGPS
logP	2.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.79	ChemAxon
pKa (Strongest Basic)	10.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.05 m³·mol⁻¹	ChemAxon
Polarizability	32.58 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00024608

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101104094

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tuboxenine (NP0066950)

MOL for NP0066950 (Tuboxenine)

3D MOL for NP0066950 (Tuboxenine)

3D SDF for NP0066950 (Tuboxenine)

3D-SDF for NP0066950 (Tuboxenine)

PDB for NP0066950 (Tuboxenine)

3D PDB for NP0066950 (Tuboxenine)

SMILES for NP0066950 (Tuboxenine)

INCHI for NP0066950 (Tuboxenine)

Structure for NP0066950 (Tuboxenine)

3D Structure for NP0066950 (Tuboxenine)