NP-MRD: Showing NP-Card for 16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one (NP0186813)

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Record Information

Version

2.0

Created at

2022-09-04 02:47:08 UTC

Updated at

2022-09-04 02:47:08 UTC

NP-MRD ID

NP0186813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one

Description

SCHEMBL3094766 belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. 16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one is found in Sciadotenia toxifera and Telitoxicum peruvianum. SCHEMBL3094766 is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -4.1865   -1.7349   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -2.0137   -0.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9420   -0.9548   -0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    0.3296   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838    1.4144   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    2.6784   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312    3.7207   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0795    3.4900    0.1262 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.2339    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351    1.1572   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2586   -0.1706    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -1.2293   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2941   -2.5958   -0.1677 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075   -0.3997    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964   -1.6742    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814   -1.8465    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029   -0.7711    0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8957    0.5007    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5316    0.7070    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437    2.0767    0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873    3.0784    0.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5375   -1.2607    0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7117   -2.6881   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3342   -0.9967   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4812    0.5529   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    2.8758   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6531    4.7250   -0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822   -3.1136   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -3.1242    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6506   -2.5659    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -2.8684    0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4775   -0.9091    0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5271    1.3761    0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 10  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
  5  4  2  0
  4  3  1  0
 14 11  1  0
  9 10  1  0
 14 19  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 28  1  0
 13 29  1  0
  6 26  1  0
  7 27  1  0
 18 33  1  0
 17 32  1  0
 16 31  1  0
 15 30  1  0
  4 25  1  0
M  END


  Mrv1533004191516552D          

 21 24  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  2  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
  5 21  1  0  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(N)C2=C3C(C=CN=C3C(=O)C3=CC=CC=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12N2O2/c1-21-12-8-9-6-7-19-16-13(9)14(15(12)18)10-4-2-3-5-11(10)17(16)20/h2-8H,18H2,1H3

> <INCHI_KEY>
NVXRXLMYVLNDKS-UHFFFAOYSA-N

> <FORMULA>
C17H12N2O2

> <MOLECULAR_WEIGHT>
276.295

> <EXACT_MASS>
276.089877634

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.934958669078014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,9,11,13,15-octaen-8-one

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.277635835

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.896083610957124

> <JCHEM_PKA_STRONGEST_BASIC>
3.9766089601238295

> <JCHEM_POLAR_SURFACE_AREA>
65.21

> <JCHEM_REFRACTIVITY>
80.7966

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,9,11,13,15-octaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18    3   20                                                  
CONECT   20   19                                                            
CONECT   21   18    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₂N₂O₂

Average Mass

276.2950 Da

Monoisotopic Mass

276.08988 Da

IUPAC Name

16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,9,11,13,15-octaen-8-one

Traditional Name

16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,9,11,13,15-octaen-8-one

CAS Registry Number

Not Available

SMILES

COC1=C(N)C2=C3C(C=CN=C3C(=O)C3=CC=CC=C23)=C1

InChI Identifier

InChI=1S/C17H12N2O2/c1-21-12-8-9-6-7-19-16-13(9)14(15(12)18)10-4-2-3-5-11(10)17(16)20/h2-8H,18H2,1H3

InChI Key

NVXRXLMYVLNDKS-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
Sciadotenia toxifera	LOTUS Database	35616633
Telitoxicum peruvianum Moldenke	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Isoquinoline
Quinoline
Naphthalene
Methoxyaniline
Anisole
Aryl ketone
Phenol ether
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Ketone
Ether
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organonitrogen compound
Organooxygen 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	2.51	ALOGPS
logP	2.28	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.9	ChemAxon
pKa (Strongest Basic)	3.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.8 m³·mol⁻¹	ChemAxon
Polarizability	28.93 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

Not Available

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

11832657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one (NP0186813)

MOL for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

3D MOL for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

3D SDF for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

3D-SDF for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

PDB for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

3D PDB for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

SMILES for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

INCHI for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

Structure for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)

3D Structure for NP0186813 (16-amino-15-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one)