NP-MRD: Showing NP-Card for Quercetin 3-O-sophoroside (NP0050149)

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Record Information

Version

2.0

Created at

2022-03-17 21:24:04 UTC

Updated at

2022-03-17 21:24:04 UTC

NP-MRD ID

NP0050149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quercetin 3-O-sophoroside

Description

(2S)-2-carboxy-1-{2-[(2S)-2-carboxy-6-carboxylato-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium belongs to the class of organic compounds known as proline and derivatives. Quercetin 3-O-sophoroside is found in Beta vulgaris, Mirabilis jalapa , Opuntia ficus-indica , Portulaca grandiflora and Portulaca pilosa. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (2S)-2-carboxy-1-{2-[(2S)-2-carboxy-6-carboxylato-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304022019503D          

 22 23  0  0  0  0            999 V2000
    3.0516    2.2775    2.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6104    0.8766    2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926   -0.5150   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    2.0749    2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4168    0.7158    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7704   -1.9766   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7222    0.3589   -1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7176   -0.7122   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -2.1900   -2.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8989   -0.0989   -1.8625 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4431   -0.0320    1.8467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7443   -3.4435   -3.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4265    1.0746   -2.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -0.9373    2.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5602   -1.1230   -2.8164 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    0.8784    1.5616 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.3506   -2.9983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6957   -3.5922   -4.2547 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.5185    1.0685   -3.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8471    2.2342   -1.9380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.8133    3.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -0.7729    3.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  2  3  0  0  0
  4 16  1  0  0  0  0
  5 16  2  3  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  1  6  0  0  0
 10 15  1  0  0  0  0
 11 14  1  1  0  0  0
 11 16  1  0  0  0  0
 12 17  2  0  0  0  0
 12 18  1  0  0  0  0
 13 19  2  0  0  0  0
 13 20  1  0  0  0  0
 14 21  2  0  0  0  0
 14 22  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END
> <DATABASE_ID>
NP0050149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1CCC[N+]1=CC=C1C[C@H](NC(=C1)C([O-])=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O6/c17-12(18)9-6-8(7-10(15-9)13(19)20)3-5-16-4-1-2-11(16)14(21)22/h3,5-6,10-11H,1-2,4,7H2,(H3,17,18,19,20,21,22)/t10-,11-/m0/s1

> <INCHI_KEY>
RJIIQBYZGJSODH-QWRGUYRKSA-N

> <FORMULA>
C14H16N2O6

> <MOLECULAR_WEIGHT>
308.29

> <EXACT_MASS>
308.100836243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.734630622009963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-carboxy-1-{2-[(2S)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1lambda5-pyrrolidin-1-ylium

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-4.120196724471745

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6996592335930973

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1199313711687036

> <JCHEM_PKA_STRONGEST_BASIC>
0.08164305732449562

> <JCHEM_POLAR_SURFACE_AREA>
129.77

> <JCHEM_REFRACTIVITY>
98.0534

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-carboxy-1-{2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-1lambda5-pyrrolidin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0       3.052   2.277   2.279  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.610   0.877   2.195  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.293  -0.515  -0.003  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.583   2.075   2.352  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.417   0.716   0.753  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.977  -1.581  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.722   0.359  -1.027  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.718  -0.712  -0.860  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.672  -2.190  -2.545  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.899  -0.099  -1.863  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.443  -0.032   1.847  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.744  -3.443  -3.279  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.426   1.075  -2.577  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -0.937   2.984  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.560  -1.123  -2.816  0.00  0.00           N+0
HETATM   16  N   UNK     0       1.390   0.878   1.562  0.00  0.00           N+1
HETATM   17  O   UNK     0      -0.936  -4.351  -2.998  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.696  -3.592  -4.255  0.00  0.00           O-1
HETATM   19  O   UNK     0      -3.519   1.069  -3.832  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.847   2.234  -1.938  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.891  -1.813   3.406  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.894  -0.773   3.594  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1   11                                                       
CONECT    3    5    8                                                       
CONECT    4    1   16                                                       
CONECT    5    3   16                                                       
CONECT    6    8    9                                                       
CONECT    7    8   10                                                       
CONECT    8    3    6    7                                                  
CONECT    9    6   12   15                                                  
CONECT   10    7   13   15                                                  
CONECT   11    2   14   16                                                  
CONECT   12    9   17   18                                                  
CONECT   13   10   19   20                                                  
CONECT   14   11   21   22                                                  
CONECT   15    9   10                                                       
CONECT   16    4    5   11                                                  
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Indicaxanthin	MeSH

Chemical Formula

C₁₄H₁₆N₂O₆

Average Mass

308.2900 Da

Monoisotopic Mass

308.10084 Da

IUPAC Name

(2S)-2-carboxy-1-{2-[(2S)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1lambda5-pyrrolidin-1-ylium

Traditional Name

(2S)-2-carboxy-1-{2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-1lambda5-pyrrolidin-1-ylium

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H]1CCC[N+]1=CC=C1C[C@H](NC(=C1)C([O-])=O)C(O)=O

InChI Identifier

InChI=1S/C14H16N2O6/c17-12(18)9-6-8(7-10(15-9)13(19)20)3-5-16-4-1-2-11(16)14(21)22/h3,5-6,10-11H,1-2,4,7H2,(H3,17,18,19,20,21,22)/t10-,11-/m0/s1

InChI Key

RJIIQBYZGJSODH-QWRGUYRKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Beta vulgaris	LOTUS Database	35616633
Brassica oleracea var. italica	FooDB	PHYTOHUB
Mirabilis jalapa	Plant	KNApSAcK
Opuntia ficus-indica	Plant	KNApSAcK
Portulaca grandiflora	Plant	KNApSAcK
Portulaca pilosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Tetrahydropyridine
Hydropyridine
Pyrrolidine
Amino acid
Carboxylic acid salt
Shiff base
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Secondary aliphatic amine
Enamine
Secondary amine
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Organic zwitterion
Organic salt
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:5896 )
Betaxanthins (C08549 )

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	ALOGPS
logP	-4.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	0.082	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	129.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.05 m³·mol⁻¹	ChemAxon
Polarizability	29.73 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

C00001591

Chemspider ID

Not Available

KEGG Compound ID

C08549

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441617

PDB ID

Not Available

ChEBI ID

5896

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Quercetin 3-O-sophoroside (NP0050149)

MOL for NP0050149 (Quercetin 3-O-sophoroside)

3D MOL for NP0050149 (Quercetin 3-O-sophoroside)

3D SDF for NP0050149 (Quercetin 3-O-sophoroside)

3D-SDF for NP0050149 (Quercetin 3-O-sophoroside)

PDB for NP0050149 (Quercetin 3-O-sophoroside)

3D PDB for NP0050149 (Quercetin 3-O-sophoroside)

SMILES for NP0050149 (Quercetin 3-O-sophoroside)

INCHI for NP0050149 (Quercetin 3-O-sophoroside)

Structure for NP0050149 (Quercetin 3-O-sophoroside)

3D Structure for NP0050149 (Quercetin 3-O-sophoroside)