NP-MRD: Showing NP-Card for Acanthomine A (NP0081936)

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Record Information

Version

2.0

Created at

2022-04-29 02:59:56 UTC

Updated at

2022-04-29 02:59:56 UTC

NP-MRD ID

NP0081936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acanthomine A

Description

Accanthomine A belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Acanthomine A is found in Acanthostrongylophora ingens. Based on a literature review very few articles have been published on accanthomine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.1399    0.3968    3.6160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889    0.2956    2.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5213    0.2803    1.6584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    0.1842    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954    0.0996   -0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172    0.1164    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.0256   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -0.0653   -2.1353 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -0.1593   -3.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -0.1692   -2.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -0.0595   -1.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1705    0.0297   -0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373    0.1172    0.8825 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    0.0865    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414    0.1426    1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2825    0.0896    1.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614   -0.0200    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6913   -0.0764   -0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -0.0217   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522    0.2123    1.3672 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050    1.0895    4.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438   -0.2482    4.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6989    0.1748   -0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7275    0.0234   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318    0.6674   -3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232   -1.0961   -3.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721    0.5885   -3.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471   -1.2048   -2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    0.1955    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.2289    2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0240    0.1354    2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969   -0.0645   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.1618   -1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 20  2  0
 20  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  3  2  1  0
 12  7  1  0
 19 14  1  0
 19 11  1  0
  1 21  1  0
  1 22  1  0
  5 24  1  0
  4 23  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652304292204592D          

 20 23  0  0  0  0            999 V2000
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566   -1.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -2.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -2.7260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573   -2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -1.3283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -2.2844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    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  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  6 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
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  1 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0081936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=CC=N1)C1=NCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C15H13N5/c16-15-18-8-6-12(20-15)14-13-10(5-7-17-14)9-3-1-2-4-11(9)19-13/h1-4,6,8,19H,5,7H2,(H2,16,18,20)

> <INCHI_KEY>
NFXSUBLDOSKHAN-UHFFFAOYSA-N

> <FORMULA>
C15H13N5

> <MOLECULAR_WEIGHT>
263.304

> <EXACT_MASS>
263.117095439

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.452496568156327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{3H,4H,9H-pyrido[3,4-b]indol-1-yl}pyrimidin-2-amine

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.039788089

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.341945796822884

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.495936483767025

> <JCHEM_PKA_STRONGEST_BASIC>
4.7395575465283795

> <JCHEM_POLAR_SURFACE_AREA>
79.95

> <JCHEM_REFRACTIVITY>
78.79960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{3H,4H,9H-pyrido[3,4-b]indol-1-yl}pyrimidin-2-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.412  -3.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.936  -4.768   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.570  -5.089   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.600  -3.944   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.124  -2.479   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -3.107  -4.264   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
CONECT    1    2    5   20                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3                                                       
CONECT   10    6   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    1                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃N₅

Average Mass

263.3040 Da

Monoisotopic Mass

263.11710 Da

IUPAC Name

4-{3H,4H,9H-pyrido[3,4-b]indol-1-yl}pyrimidin-2-amine

Traditional Name

4-{3H,4H,9H-pyrido[3,4-b]indol-1-yl}pyrimidin-2-amine

CAS Registry Number

Not Available

SMILES

NC1=NC(=CC=N1)C1=NCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C15H13N5/c16-15-18-8-6-12(20-15)14-13-10(5-7-17-14)9-3-1-2-4-11(9)19-13/h1-4,6,8,19H,5,7H2,(H2,16,18,20)

InChI Key

NFXSUBLDOSKHAN-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, 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
Acanthostrongylophora ingens	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Pyridopyrimidine
3-alkylindole
Indole
Indole or derivatives
Aminopyrimidine
Benzenoid
Pyrimidine
Pyrrole
Heteroaromatic compound
Ketimine
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Imine
Organopnictogen compound
Organic nitrogen compound
Primary 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	2.03	ALOGPS
logP	2.04	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	4.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.95 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.8 m³·mol⁻¹	ChemAxon
Polarizability	28.45 Å³	ChemAxon
Number of Rings	4	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

C00048596

Chemspider ID

24741793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139076140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acanthomine A (NP0081936)

MOL for NP0081936 (Acanthomine A)

3D MOL for NP0081936 (Acanthomine A)

3D SDF for NP0081936 (Acanthomine A)

3D-SDF for NP0081936 (Acanthomine A)

PDB for NP0081936 (Acanthomine A)

3D PDB for NP0081936 (Acanthomine A)

SMILES for NP0081936 (Acanthomine A)

INCHI for NP0081936 (Acanthomine A)

Structure for NP0081936 (Acanthomine A)

3D Structure for NP0081936 (Acanthomine A)