NP-MRD: Showing NP-Card for Echinoramine I (NP0083519)

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Record Information

Version

2.0

Created at

2022-04-29 04:32:28 UTC

Updated at

2022-04-29 04:32:28 UTC

NP-MRD ID

NP0083519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Echinoramine I

Description

CTK8J5160 belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Echinoramine I is found in Echinops ritro. CTK8J5160 is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -0.0774   -2.0194   -2.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920   -0.8240   -2.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145   -0.1428   -1.0172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4287   -0.0699   -0.1911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1164    0.8991    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970    2.2959    0.7239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.4798    2.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661   -1.2110    0.4643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4822   -2.2342   -0.4553 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3834   -0.7638    1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4507   -1.3033    0.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428    0.2329    2.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783    1.2888   -1.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183    2.1431   -1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    1.8574   -0.3609 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8627    2.8353   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9147    0.5502    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775    0.2495    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523   -1.0253    1.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863   -1.9512    1.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0384   -1.6731    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.3814   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -1.9811   -3.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6601   -2.7694   -2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -2.5164   -2.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2070    0.4852   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296    2.8877    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7157    2.7846    0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -1.6063    1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8425   -3.0828    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2259   -1.8459   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188   -0.0026    2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767    1.5795   -2.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806    3.1486   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687    2.4892   -0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    3.7843   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8347    3.0024    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    1.0268    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8805   -1.2426    2.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1526   -2.9395    1.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -2.4346    0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  3  4  1  0
  4  8  1  0
  8  9  1  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
 22  3  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
  4 26  1  6
  8 29  1  1
  9 30  1  0
  9 31  1  0
 12 32  1  0
  6 27  1  0
  6 28  1  0
M  END


  Mrv1533004251509092D          

 22 23  0  0  0  0            999 V2000
    5.2953    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7650   -0.2368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -0.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    1.1705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616    1.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9866    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990    2.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3293    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0471    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2347    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -2.1560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091   -1.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236   -0.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -2.1560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815   -0.9185    0.0000 N   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  1  0  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(C=CN(C)C2=CC=CC=C12)C(C(N)C(O)=O)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H19N3O4/c1-18-8-7-15(22-2,9-5-3-4-6-10(9)18)11(13(17)19)12(16)14(20)21/h3-8,11-12H,16H2,1-2H3,(H2,17,19)(H,20,21)

> <INCHI_KEY>
SHANZLCFUGOMJA-UHFFFAOYSA-N

> <FORMULA>
C15H19N3O4

> <MOLECULAR_WEIGHT>
305.334

> <EXACT_MASS>
305.137556104

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.503520307503948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-carbamoyl-3-(4-methoxy-1-methyl-1,4-dihydroquinolin-4-yl)propanoic acid

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
-2.435899258836839

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.035047101910827

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1776519970378474

> <JCHEM_PKA_STRONGEST_BASIC>
8.379130851989661

> <JCHEM_POLAR_SURFACE_AREA>
118.88000000000001

> <JCHEM_REFRACTIVITY>
80.93539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-carbamoyl-3-(4-methoxy-1-methylquinolin-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       9.885   0.738   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.895  -0.442   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.378  -0.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.861  -0.442   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.872   0.738   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.398   2.185   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.408   3.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.915   2.452   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.442   3.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.958   4.167   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.948   2.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.421   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.905   1.273   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.378  -1.715   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.044  -2.485   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.044  -4.025   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.711  -1.715   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.377  -2.485   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.711  -0.175   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.712  -2.485   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.712  -4.025   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      10.045  -1.715   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13   14                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3    8                                                  
CONECT   14    3   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉N₃O₄

Average Mass

305.3340 Da

Monoisotopic Mass

305.13756 Da

IUPAC Name

2-amino-3-carbamoyl-3-(4-methoxy-1-methyl-1,4-dihydroquinolin-4-yl)propanoic acid

Traditional Name

2-amino-3-carbamoyl-3-(4-methoxy-1-methylquinolin-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

COC1(C=CN(C)C2=CC=CC=C12)C(C(N)C(O)=O)C(N)=O

InChI Identifier

InChI=1S/C15H19N3O4/c1-18-8-7-15(22-2,9-5-3-4-6-10(9)18)11(13(17)19)12(16)14(20)21/h3-8,11-12H,16H2,1-2H3,(H2,17,19)(H,20,21)

InChI Key

SHANZLCFUGOMJA-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
Echinops ritro	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Alpha-amino acid
Alpha-amino acid or derivatives
Dihydroquinoline
Tertiary aliphatic/aromatic amine
Aralkylamine
Fatty amide
Fatty acyl
Benzenoid
Amino acid or derivatives
Carboxamide group
Amino acid
Tertiary amine
Primary carboxylic acid amide
Allylamine
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Enamine
Ether
Azacycle
Monocarboxylic acid or derivatives
Organic oxide
Amine
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Primary aliphatic amine
Organic oxygen compound
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	-0.63	ALOGPS
logP	-2.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.18	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.88 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.94 m³·mol⁻¹	ChemAxon
Polarizability	30.5 Å³	ChemAxon
Number of Rings	2	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

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

71438787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Echinoramine I (NP0083519)

MOL for NP0083519 (Echinoramine I)

3D MOL for NP0083519 (Echinoramine I)

3D SDF for NP0083519 (Echinoramine I)

3D-SDF for NP0083519 (Echinoramine I)

PDB for NP0083519 (Echinoramine I)

3D PDB for NP0083519 (Echinoramine I)

SMILES for NP0083519 (Echinoramine I)

INCHI for NP0083519 (Echinoramine I)

Structure for NP0083519 (Echinoramine I)

3D Structure for NP0083519 (Echinoramine I)