NP-MRD: Showing NP-Card for Isomethuenine (NP0068053)

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Record Information

Version

2.0

Created at

2022-04-28 12:57:02 UTC

Updated at

2022-04-28 12:57:02 UTC

NP-MRD ID

NP0068053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isomethuenine

Description

16-Epimethuenine belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Isomethuenine is found in Tabernaemontana coffeoides, Tabernaemontana coffeoides Boj., Tabernaemontana dichotoma Roxb.ex Wall , Tabernaemontana inconspicua and Tabernaemontana pauciflora. Isomethuenine was first documented in 1985 (PMID: 3866005). Based on a literature review very few articles have been published on 16-epimethuenine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -1.9902   -1.4300    2.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -1.0796    1.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257   -0.3493    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6131    0.0185   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276   -0.4217   -1.6048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.6885   -2.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -0.9547   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047    0.1310   -0.8488 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5013    0.0119   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457    0.3411   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889    1.0508    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7351    1.1017    1.4236 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    0.4268    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9281    0.1650    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063   -0.5551   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8885   -1.0333   -1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -0.7801   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549   -0.0577   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3607    1.6989    1.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    2.4979    2.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    1.5247    1.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390    0.1634    0.5888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5523   -0.5564    3.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.0179    3.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234   -2.1104    2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262   -1.4023    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055    1.1035   -0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5658   -0.4977   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120    1.6763   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9480    0.5653   -3.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726    0.6027   -3.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495   -1.2013   -2.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7992   -1.7914   -0.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    1.0910   -1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6653   -1.0716   -1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645    0.5449   -2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727    1.5789    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4834    0.5392    1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6700   -0.7593   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -1.6057   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935   -1.1739   -2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029    2.3409    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    1.5297    2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615   -0.5433    1.1260 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  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  3  1  0
 22  8  1  0
 18 10  1  0
 18 13  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
  6 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  6
  9 35  1  0
  9 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  1
M  END


  Mrv1652304282214572D          

 22 25  0  0  1  0            999 V2000
    4.0954    3.6703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7237    2.9338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9161    2.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2807    3.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2960    4.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    4.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    5.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7513    4.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    4.3858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    3.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4915    3.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    2.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201    2.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1524    2.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971    3.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1757    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993    2.2900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3710    3.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9190    3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2907    4.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8387    5.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    1.5998    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
  6  8  1  0  0  0  0
  1  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  2  0  0  0  0
  2 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN(C)C[C@@H]2CC3=C(NC4=CC=CC=C34)C(=O)C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-3-12-10-21(2)11-13-8-16-14-6-4-5-7-17(14)20-19(16)18(22)9-15(12)13/h3-7,13,15,20H,8-11H2,1-2H3/b12-3-/t13-,15-/m0/s1

> <INCHI_KEY>
GCVROCDNUNQXAD-GDJCJWFOSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.277392307571624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,7E,8R)-7-ethylidene-5-methyl-5,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-1(11),13,15,17-tetraen-10-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.676899147333333

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.258211420115348

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.538642821674873

> <JCHEM_PKA_STRONGEST_BASIC>
7.038823488900728

> <JCHEM_POLAR_SURFACE_AREA>
36.1

> <JCHEM_REFRACTIVITY>
90.6814

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,7E,8R)-7-ethylidene-5-methyl-5,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-1(11),13,15,17-tetraen-10-one

> <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       7.645   6.851   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.951   5.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.443   5.162   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.257   6.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.286   7.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.508   8.621   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.193  10.129   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.002   8.251   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.830   8.187   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.902   6.958   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.784   5.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.132   4.300   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.597   4.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.284   5.430   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.368   6.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.795   4.188   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.332   4.275   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      10.026   5.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.182   6.938   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.876   8.313   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.032   9.601   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.176   2.986   0.000  0.00  0.00           C+0
CONECT    1    2    8   19                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    1                                                       
CONECT    9    5   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    2   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O

Average Mass

294.3980 Da

Monoisotopic Mass

294.17321 Da

IUPAC Name

(3R,7E,8R)-7-ethylidene-5-methyl-5,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-1(11),13,15,17-tetraen-10-one

Traditional Name

(3R,7E,8R)-7-ethylidene-5-methyl-5,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-1(11),13,15,17-tetraen-10-one

CAS Registry Number

Not Available

SMILES

C\C=C1\CN(C)C[C@@H]2CC3=C(NC4=CC=CC=C34)C(=O)C[C@@H]12

InChI Identifier

InChI=1S/C19H22N2O/c1-3-12-10-21(2)11-13-8-16-14-6-4-5-7-17(14)20-19(16)18(22)9-15(12)13/h3-7,13,15,20H,8-11H2,1-2H3/b12-3-/t13-,15-/m0/s1

InChI Key

GCVROCDNUNQXAD-GDJCJWFOSA-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
Tabernaemontana coffeoides	LOTUS Database	35616633
Tabernaemontana coffeoides Boj.	Plant	KNApSAcK
Tabernaemontana dichotoma Roxb.ex Wall	Plant	KNApSAcK
Tabernaemontana inconspicua	LOTUS Database	35616633
Tabernaemontana pauciflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aryl ketone
Aryl alkyl ketone
Aralkylamine
Piperidine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aldehyde
Organic nitrogen compound
Organooxygen compound
Organonitrogen 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	2.95	ALOGPS
logP	2.68	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.1 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.68 m³·mol⁻¹	ChemAxon
Polarizability	34.28 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

4944734

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bakana P, Laekeman GM, Totte J, Herman AG, Vlietinck AJ: Stereochemical considerations in relation to the pharmacological activity of Pterotaberna alkaloids. J Nat Prod. 1985 Sep-Oct;48(5):766-71. doi: 10.1021/np50041a008. [PubMed:3866005 ]

Showing NP-Card for Isomethuenine (NP0068053)

MOL for NP0068053 (Isomethuenine)

3D MOL for NP0068053 (Isomethuenine)

3D SDF for NP0068053 (Isomethuenine)

3D-SDF for NP0068053 (Isomethuenine)

PDB for NP0068053 (Isomethuenine)

3D PDB for NP0068053 (Isomethuenine)

SMILES for NP0068053 (Isomethuenine)

INCHI for NP0068053 (Isomethuenine)

Structure for NP0068053 (Isomethuenine)

3D Structure for NP0068053 (Isomethuenine)