NP-MRD: Showing NP-Card for grisechelin I (NP0333001)

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Record Information

Version

2.0

Created at

2024-05-03 06:37:42 UTC

Updated at

2024-09-03 04:20:54 UTC

NP-MRD ID

NP0333001

Natural Product DOI

https://doi.org/10.57994/2290

Secondary Accession Numbers

None

Natural Product Identification

Common Name

grisechelin I

Description

Grisechelin I belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. grisechelin I was first documented in 2024 (PMID: 38301035). Based on a literature review very few articles have been published on grisechelin I.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01152309142D          

 25 28  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   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 C   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
    3.5724   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -2.4705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2288   -3.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163   -4.1102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683   -4.7232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1968   -5.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121   -5.7852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8099   -6.0823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094   -5.2424    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -4.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -3.5672    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -1.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537   -1.3144    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 17 21  1  1  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 14 24  2  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CSC(=N1)C1=CSC(=N1)C1=NC2=CC=CC=C2C=C1O)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N4O2S2/c17-14(22)10-6-23-15(19-10)11-7-24-16(20-11)13-12(21)5-8-3-1-2-4-9(8)18-13/h1-5,7,10,21H,6H2,(H2,17,22)/t10-/m0/s1

> <INCHI_KEY>
NKKFUAQFDQFFRY-JTQLQIEISA-N

> <FORMULA>
C16H12N4O2S2

> <MOLECULAR_WEIGHT>
356.42

> <EXACT_MASS>
356.04016799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
36.289542960594595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-2-[2-(3-hydroxyquinolin-2-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,3-thiazole-4-carboxamide

> <JCHEM_LOGP>
2.528829495333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.93763605049304

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.700497376943432

> <JCHEM_PKA_STRONGEST_BASIC>
1.2662233190000654

> <JCHEM_POLAR_SURFACE_AREA>
101.46000000000001

> <JCHEM_REFRACTIVITY>
102.68729999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-2-[2-(3-hydroxyquinolin-2-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,3-thiazole-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JAN-23         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.161  -4.612   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.667  -4.932   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.294  -6.339   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.524  -7.672   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.554  -8.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.234 -10.323   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.769 -10.799   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -3.378 -11.354   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -3.751  -9.786   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -3.961  -8.190   0.000  0.00  0.00           C+0
HETATM   23  S   UNK     0      -3.800  -6.659   0.000  0.00  0.00           S+0
HETATM   24  C   UNK     0      -2.437  -3.598   0.000  0.00  0.00           C+0
HETATM   25  S   UNK     0      -1.407  -2.454   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21   22                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   17   23                                                       
CONECT   23   22   15                                                       
CONECT   24   14   25                                                       
CONECT   25   24   12                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂N₄O₂S₂

Average Mass

356.4200 Da

Monoisotopic Mass

356.04017 Da

IUPAC Name

(4R)-2-[2-(3-hydroxyquinolin-2-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,3-thiazole-4-carboxamide

Traditional Name

(4R)-2-[2-(3-hydroxyquinolin-2-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,3-thiazole-4-carboxamide

CAS Registry Number

Not Available

SMILES

[H][C@]1(CSC(=N1)C1=CSC(=N1)C1=NC2=CC=CC=C2C=C1O)C(N)=O

InChI Identifier

InChI=1S/C16H12N4O2S2/c17-14(22)10-6-23-15(19-10)11-7-24-16(20-11)13-12(21)5-8-3-1-2-4-9(8)18-13/h1-5,7,10,21H,6H2,(H2,17,22)/t10-/m0/s1

InChI Key

NKKFUAQFDQFFRY-JTQLQIEISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhang@scsio.ac.cn	Not Available	Not Available	2024-05-03	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhang@scsio.ac.cn	Not Available	Not Available	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhang@scsio.ac.cn	Not Available	Not Available	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C2D6OS, experimental)	wzhang@scsio.ac.cn	Not Available	Not Available	2024-05-03	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 176 MHz, C2D6OS, experimental)	wzhang@scsio.ac.cn	Not Available	Not Available	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, C2D6OS, experimental)	wzhang@scsio.ac.cn	Not Available	Not Available	2024-05-03	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700.18490126, C2D6OS, simulated)	wzhang@scsio.ac.cn	South China Sea Institute of Oceanology, CAS	Wenjun Zhang	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
sp. SCSIO 40025		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as cysteine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Quinoline
Thiazolecarboxamide
Hydroxypyridine
Imidothiolactone
Benzenoid
Pyridine
Heteroaromatic compound
Meta-thiazoline
Thiazole
Secondary ketimine
Azole
Ketimine
Imidothioester
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Imidothioic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Imine
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	2.53	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	1.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.69 m³·mol⁻¹	ChemAxon
Polarizability	36.29 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu W, Zhai S, Zhang L, Chen Y, Liu Z, Ma W, Zhang T, Zhang W, Ma L, Zhang C, Zhang W: Expanding the Chemical Diversity of Grisechelins via Heterologous Expression. J Nat Prod. 2024 Feb 23;87(2):371-380. doi: 10.1021/acs.jnatprod.3c01132. Epub 2024 Feb 1. [PubMed:38301035 ]

Showing NP-Card for grisechelin I (NP0333001)

MOL for NP0333001 (grisechelin I)

3D MOL for NP0333001 (grisechelin I)

3D SDF for NP0333001 (grisechelin I)

3D-SDF for NP0333001 (grisechelin I)

PDB for NP0333001 (grisechelin I)

3D PDB for NP0333001 (grisechelin I)

SMILES for NP0333001 (grisechelin I)

INCHI for NP0333001 (grisechelin I)

Structure for NP0333001 (grisechelin I)

3D Structure for NP0333001 (grisechelin I)