NP-MRD: Showing NP-Card for 20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol (NP0158126)

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Record Information

Version

2.0

Created at

2022-09-02 15:39:38 UTC

Updated at

2022-09-02 15:39:38 UTC

NP-MRD ID

NP0158126

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol

Description

Janussine A belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol is found in Strychnos johnsonii. Based on a literature review very few articles have been published on janussine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217392D          

 34 41  0  0  0  0            999 V2000
    1.3340    1.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    0.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396    0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920    1.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156    1.1007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680    1.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8916    1.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107    0.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271   -0.3262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0986   -0.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9115   -0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 20  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217392D          

 34 41  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0158126

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1N2C3C(CCNC3CC3CC4N(CCC5=C4NC4=CC=C(O)C=C54)C=C13)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C29H32N4O/c1-16-23-15-32-11-9-20-22-14-18(34)6-7-24(22)31-28(20)27(32)13-17(23)12-25-29-21(8-10-30-25)19-4-2-3-5-26(19)33(16)29/h2-7,14-17,21,25,27,29-31,34H,8-13H2,1H3

> <INCHI_KEY>
VNSRPOPXZODCJM-UHFFFAOYSA-N

> <FORMULA>
C29H32N4O

> <MOLECULAR_WEIGHT>
452.602

> <EXACT_MASS>
452.257611666

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.27686080413074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{8,13}.0^{22,27}.0^{28,32}]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.2956083812636128

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
17.41499284613993

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.411751981779393

> <JCHEM_PKA_STRONGEST_BASIC>
10.083992437488106

> <JCHEM_POLAR_SURFACE_AREA>
54.53000000000001

> <JCHEM_REFRACTIVITY>
136.39269999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{8,13}.0^{22,27}.0^{28,32}]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol

> <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       2.490   2.664   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.860   1.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.367   0.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.212   2.142   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.749   2.055   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.594   3.342   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.131   3.255   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.824   1.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.980   0.592   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.944  -0.609   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.384  -0.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.753  -0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.048   0.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.974   1.603   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.269   2.436   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.605   2.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.310   1.475   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.442   0.679   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.598  -0.608   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.061  -0.521   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.418  -1.921   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.923  -2.290   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.572  -3.874   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       1.116  -4.376   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.047  -3.366   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.246  -1.855   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.682  -0.625   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.216  -0.492   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.868   0.903   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.985   2.165   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.451   2.032   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.201   0.637   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       1.674   0.188   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       1.701  -1.352   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    8   11                                                  
CONECT   18    9    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32    2   34                                                  
CONECT   34   33   22   26                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂N₄O

Average Mass

452.6020 Da

Monoisotopic Mass

452.25761 Da

IUPAC Name

20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{8,13}.0^{22,27}.0^{28,32}]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol

Traditional Name

20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{8,13}.0^{22,27}.0^{28,32}]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol

CAS Registry Number

Not Available

SMILES

CC1N2C3C(CCNC3CC3CC4N(CCC5=C4NC4=CC=C(O)C=C54)C=C13)C1=CC=CC=C21

InChI Identifier

InChI=1S/C29H32N4O/c1-16-23-15-32-11-9-20-22-14-18(34)6-7-24(22)31-28(20)27(32)13-17(23)12-25-29-21(8-10-30-25)19-4-2-3-5-26(19)33(16)29/h2-7,14-17,21,25,27,29-31,34H,8-13H2,1H3

InChI Key

VNSRPOPXZODCJM-UHFFFAOYSA-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
Strychnos johnsonii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
3-alkylindole
Hydroxyindole
Indole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
Azepane
Tetrahydropyridine
Phenol
1-hydroxy-2-unsubstituted benzenoid
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Secondary aliphatic amine
Enamine
Allylamine
Azacycle
Secondary amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen 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	3.71	ALOGPS
logP	3.3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	10.08	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	54.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	136.39 m³·mol⁻¹	ChemAxon
Polarizability	52.28 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

23327490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol (NP0158126)

MOL for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

3D MOL for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

3D SDF for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

3D-SDF for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

PDB for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

3D PDB for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

SMILES for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

INCHI for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

Structure for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)

3D Structure for NP0158126 (20-methyl-7,17,21,31-tetraazaoctacyclo[19.10.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁸,¹³.0²²,²⁷.0²⁸,³²]dotriaconta-6(14),8,10,12,18,22,24,26-octaen-11-ol)