NP-MRD: Showing NP-Card for (+)-Sterculinine II (NP0068427)

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Record Information

Version

2.0

Created at

2022-04-28 13:36:21 UTC

Updated at

2022-04-28 13:36:21 UTC

NP-MRD ID

NP0068427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sterculinine II

Description

(2S)-2-{[hydroxy(2-hydroxyquinolin-4-yl)methylidene]amino}-4-methoxy-4-oxobutanoic acid belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (+)-Sterculinine II is found in Sterculia lychnophora. Based on a literature review very few articles have been published on (2S)-2-{[hydroxy(2-hydroxyquinolin-4-yl)methylidene]amino}-4-methoxy-4-oxobutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    4.3804    1.9265   -1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063    0.6238   -1.2173 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257    0.4068   -0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    1.3986    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0339   -0.9227    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -0.9773    1.3205 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6207   -0.6411    0.6743 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -1.5695    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396   -2.7188    1.1173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6907   -1.3042    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945   -2.2910   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3506   -2.0506   -1.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8105   -2.9385   -2.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9583   -0.8655   -1.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089    0.0955   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1685    1.2905   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343    2.2801    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814    2.0858    1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9126    0.8791    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3363   -0.1076    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826   -0.1334    2.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982    0.7631    2.8636 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512   -0.3228    3.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    1.8471   -2.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6114    2.6018   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448    2.2262   -2.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621   -1.2165    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8199   -1.6440   -0.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -2.0411    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830    0.3034    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -3.2438   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8391   -0.7145   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0743    1.4234   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2805    3.2115    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328    2.8455    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0407    0.7310    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -1.2368    3.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 23  1  0
 21 22  2  0
 20 10  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  1
  7 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
M  END


  Mrv1652304282215362D          

 23 24  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    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
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   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
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    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
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  1  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
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    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
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H](NC(=O)C1=CC(=O)NC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O6/c1-23-13(19)7-11(15(21)22)17-14(20)9-6-12(18)16-10-5-3-2-4-8(9)10/h2-6,11H,7H2,1H3,(H,16,18)(H,17,20)(H,21,22)/t11-/m0/s1

> <INCHI_KEY>
DTWJLKCBGPJKQZ-NSHDSACASA-N

> <FORMULA>
C15H14N2O6

> <MOLECULAR_WEIGHT>
318.285

> <EXACT_MASS>
318.085186179

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.3042750042317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-methoxy-4-oxo-2-[(2-oxo-1,2-dihydroquinolin-4-yl)formamido]butanoic acid

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
0.05579269433333384

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.102832745094638

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3961892845409696

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9121070585915775

> <JCHEM_POLAR_SURFACE_AREA>
121.80000000000003

> <JCHEM_REFRACTIVITY>
79.38029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-methoxy-4-oxo-2-[(2-oxo-1H-quinolin-4-yl)formamido]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.334  -3.850   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[hydroxy(2-hydroxyquinolin-4-yl)methylidene]amino}-4-methoxy-4-oxobutanoate	Generator

Chemical Formula

C₁₅H₁₄N₂O₆

Average Mass

318.2850 Da

Monoisotopic Mass

318.08519 Da

IUPAC Name

(2S)-4-methoxy-4-oxo-2-[(2-oxo-1,2-dihydroquinolin-4-yl)formamido]butanoic acid

Traditional Name

(2S)-4-methoxy-4-oxo-2-[(2-oxo-1H-quinolin-4-yl)formamido]butanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H](NC(=O)C1=CC(=O)NC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C15H14N2O6/c1-23-13(19)7-11(15(21)22)17-14(20)9-6-12(18)16-10-5-3-2-4-8(9)10/h2-6,11H,7H2,1H3,(H,16,18)(H,17,20)(H,21,22)/t11-/m0/s1

InChI Key

DTWJLKCBGPJKQZ-NSHDSACASA-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
Sterculia lychnophora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Quinolone
Hydroxyquinoline
Quinoline
Hydroxypyridine
Fatty acid methyl ester
Fatty acid ester
Fatty acyl
Benzenoid
Pyridine
Dicarboxylic acid or derivatives
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.59	ALOGPS
logP	0.056	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.8 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	30.3 Å³	ChemAxon
Number of Rings	2	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

162971478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Sterculinine II (NP0068427)

MOL for NP0068427 ((+)-Sterculinine II)

3D MOL for NP0068427 ((+)-Sterculinine II)

3D SDF for NP0068427 ((+)-Sterculinine II)

3D-SDF for NP0068427 ((+)-Sterculinine II)

PDB for NP0068427 ((+)-Sterculinine II)

3D PDB for NP0068427 ((+)-Sterculinine II)

SMILES for NP0068427 ((+)-Sterculinine II)

INCHI for NP0068427 ((+)-Sterculinine II)

Structure for NP0068427 ((+)-Sterculinine II)

3D Structure for NP0068427 ((+)-Sterculinine II)