NP-MRD: Showing NP-Card for n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid (NP0222402)

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Record Information

Version

2.0

Created at

2022-09-06 00:13:54 UTC

Updated at

2022-09-06 00:13:54 UTC

NP-MRD ID

NP0222402

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid

Description

N-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid 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. n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid is found in Streptomyces caelestis. N-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161509452D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161509452D          

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 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222402

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)C(NC(=O)C1CCCN1)C1OC(SCCOC(=O)C2=CC=CC=C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34N2O9S/c1-12(32-2)16(25-21(30)14-7-5-9-24-14)20-18(28)17(27)19(29)23(34-20)35-11-10-33-22(31)13-6-3-4-8-15(13)26/h3-4,6,8,12,14,16-20,23-24,26-29H,5,7,9-11H2,1-2H3,(H,25,30)

> <INCHI_KEY>
JGNMAXOBERVZHJ-UHFFFAOYSA-N

> <FORMULA>
C23H34N2O9S

> <MOLECULAR_WEIGHT>
514.59

> <EXACT_MASS>
514.198501857

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.233736687075805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3,4,5-trihydroxy-6-{2-methoxy-1-[(pyrrolidin-2-yl)formamido]propyl}oxan-2-yl)sulfanyl]ethyl 2-hydroxybenzoate

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-0.05136556395151237

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.252357071054176

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.062092693091527

> <JCHEM_PKA_STRONGEST_BASIC>
9.457111263238373

> <JCHEM_POLAR_SURFACE_AREA>
166.81

> <JCHEM_REFRACTIVITY>
126.74759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({3,4,5-trihydroxy-6-[2-methoxy-1-(pyrrolidin-2-ylformamido)propyl]oxan-2-yl}sulfanyl)ethyl 2-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.742  -7.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.772  -8.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.002  -9.552   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -5.496  -9.232   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0       4.001  -6.930   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
CONECT   14    5   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
CONECT   30   16   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   14   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
N-[2-Methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidate	Generator
N-[2-Methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulphanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidate	Generator
N-[2-Methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulphanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid	Generator

Chemical Formula

C₂₃H₃₄N₂O₉S

Average Mass

514.5900 Da

Monoisotopic Mass

514.19850 Da

IUPAC Name

2-[(3,4,5-trihydroxy-6-{2-methoxy-1-[(pyrrolidin-2-yl)formamido]propyl}oxan-2-yl)sulfanyl]ethyl 2-hydroxybenzoate

Traditional Name

2-({3,4,5-trihydroxy-6-[2-methoxy-1-(pyrrolidin-2-ylformamido)propyl]oxan-2-yl}sulfanyl)ethyl 2-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC(C)C(NC(=O)C1CCCN1)C1OC(SCCOC(=O)C2=CC=CC=C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C23H34N2O9S/c1-12(32-2)16(25-21(30)14-7-5-9-24-14)20-18(28)17(27)19(29)23(34-20)35-11-10-33-22(31)13-6-3-4-8-15(13)26/h3-4,6,8,12,14,16-20,23-24,26-29H,5,7,9-11H2,1-2H3,(H,25,30)

InChI Key

JGNMAXOBERVZHJ-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
Streptomyces caelestis	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 amide
O-hydroxybenzoic acid ester
Glycosyl compound
S-glycosyl compound
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Pyrrolidine-2-carboxamide
Pyrrolidine carboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Pyrrolidine
Monothioacetal
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Secondary alcohol
Oxacycle
Azacycle
Dialkyl ether
Secondary aliphatic amine
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Sulfenyl compound
Secondary amine
Polyol
Amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.18	ALOGPS
logP	-0.051	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.81 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.75 m³·mol⁻¹	ChemAxon
Polarizability	53.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

191032

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid (NP0222402)

MOL for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

3D MOL for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

3D SDF for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

3D-SDF for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

PDB for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

3D PDB for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

SMILES for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

INCHI for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

Structure for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)

3D Structure for NP0222402 (n-[2-methoxy-1-(3,4,5-trihydroxy-6-{[2-(2-hydroxybenzoyloxy)ethyl]sulfanyl}oxan-2-yl)propyl]pyrrolidine-2-carboximidic acid)