NP-MRD: Showing NP-Card for [(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol (NP0281094)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 07:14:11 UTC

Updated at

2022-09-09 07:14:11 UTC

NP-MRD ID

NP0281094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

Description

Tombozine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. [(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol is found in Alstonia angustifolia. Based on a literature review very few articles have been published on Tombozine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 44 48  0  0  0  0  0  0  0  0999 V2000
    3.0684    7.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    7.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3299    5.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967    5.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    3.6844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1328    3.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446    4.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    3.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    5.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924    7.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470    1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086   -3.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351   -3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470   -1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    8.9725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319    6.1194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949    8.0095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5271    8.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0602    6.6434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    5.3864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902    1.5487    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210    1.6954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6318    3.0919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    5.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    4.9695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2159    5.5177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    6.2883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    8.2992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9499    4.2246    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    0.4816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    2.3156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1328   -3.1443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967   -5.1517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9499   -4.2246    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736   -1.2902    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  3  1  0
  6  5  1  0
  9 12  1  0
 22 14  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
 12 37  1  1
 13 38  1  0
 13 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
  8 32  1  6
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
M  END


  Mrv1652309092209142D          

 22 26  0  0  1  0            999 V2000
   -1.4389   -0.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    0.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8938    0.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1650    0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -0.2352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8279   -0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -2.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2834   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038    1.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533    0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.1310    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12  5  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN2[C@H]3CC4=C(NC5=CC=CC=C45)[C@@H]2C[C@H]1C3CO

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,13,15,17-18,20,22H,7-10H2,1H3/b11-2-/t13-,15?,17+,18+/m1/s1

> <INCHI_KEY>
VXTDUGOBAOLMED-JTZQFXNDSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <ALOGPS_LOGP>
3.09

> <ALOGPS_LOGS>
-2.98

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.686  -0.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.025   0.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.490   0.578   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.536   1.770   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.020   1.160   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.535   1.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.175   0.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.719  -0.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.545  -1.756   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.362  -3.285   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.594  -4.209   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.707  -0.627   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.262  -1.045   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.645  -0.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.131   1.168   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.354   2.105   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.622   1.232   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.120   1.591   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.180   0.473   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.741  -1.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.244  -1.362   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.184  -0.244   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O

Average Mass

294.3980 Da

Monoisotopic Mass

294.17321 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1\CN2[C@H]3CC4=C(NC5=CC=CC=C45)[C@@H]2C[C@H]1C3CO

InChI Identifier

InChI=1S/C19H22N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,13,15,17-18,20,22H,7-10H2,1H3/b11-2-/t13-,15?,17+,18+/m1/s1

InChI Key

VXTDUGOBAOLMED-JTZQFXNDSA-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
Alstonia angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Benzenoid
Piperidine
1,3-aminoalcohol
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Primary alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025193

Chemspider ID

4445238

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tombozine

METLIN ID

Not Available

PubChem Compound

5281962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol (NP0281094)

MOL for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D MOL for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D SDF for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D-SDF for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

PDB for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D PDB for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

SMILES for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

INCHI for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

Structure for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D Structure for NP0281094 ([(1s,12s,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)