NP-MRD: Showing NP-Card for Spirobrassinin (NP0047609)

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Record Information

Version

2.0

Created at

2022-03-17 20:42:59 UTC

Updated at

2022-03-17 20:42:59 UTC

NP-MRD ID

NP0047609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spirobrassinin

Description

(S)-Spirobrassinin belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole (S)-Spirobrassinin is a strong basic compound (based on its pKa). Outside of the human body, (S)-Spirobrassinin has been detected, but not quantified in, a few different foods, such as cauliflowers, chinese cabbages, and radish. Spirobrassinin is found in Brassica carinata , Brassica napus L.ssp.rapifera , Brassica oleracea, Brassica oleracea var.botrytis , Pseudomonas cichorii and Raphanus sativus subsp. longipinnatu . This could make (S)-spirobrassinin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241208332D          

 16 18  0  0  0  0            999 V2000
   -1.7324   -1.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9072   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -2.1450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -1.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -2.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8252   -0.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644   -0.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768   -0.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198   -0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198    0.4948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295    1.4851    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    2.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    0.0000    0.0000 S   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
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  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
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC1=NCC2(S1)C(=O)NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N2OS2/c1-15-10-12-6-11(16-10)7-4-2-3-5-8(7)13-9(11)14/h2-5H,6H2,1H3,(H,13,14)

> <INCHI_KEY>
FUHQSEOSBHASCH-UHFFFAOYSA-N

> <FORMULA>
C11H10N2OS2

> <MOLECULAR_WEIGHT>
250.34

> <EXACT_MASS>
250.023454332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.265382716269187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5'-(methylsulfanyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1,4]thiazole]-2-one

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.756003960666667

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.53392071518364

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.645687658516614

> <JCHEM_PKA_STRONGEST_BASIC>
3.0353252510691675

> <JCHEM_POLAR_SURFACE_AREA>
41.46

> <JCHEM_REFRACTIVITY>
69.3867

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-(methylsulfanyl)-1H,3'H-spiro[indole-3,2'-[1,4]thiazole]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.234  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.693  -2.772   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.769  -4.004   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.615  -3.387   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.002  -4.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.234  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540  -0.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.307  -1.847   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.077  -1.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.464  -0.617   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.464   0.924   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.077   1.385   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0      -0.615   2.772   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0      -1.540   4.004   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0      -0.307   0.000   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
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    4    8   10                                                  
CONECT   10    2    9   11   16                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
5'-(Methylsulphanyl)-3'H-spiro[indole-3,2'-[1,4]thiazole]-2-ol	Generator

Chemical Formula

C₁₁H₁₀N₂OS₂

Average Mass

250.3400 Da

Monoisotopic Mass

250.02345 Da

IUPAC Name

5'-(methylsulfanyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1,4]thiazole]-2-one

Traditional Name

5'-(methylsulfanyl)-1H,3'H-spiro[indole-3,2'-[1,4]thiazole]-2-one

CAS Registry Number

113866-40-3

SMILES

CSC1=NCC2(S1)C(=O)NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C11H10N2OS2/c1-15-10-12-6-11(16-10)7-4-2-3-5-8(7)13-9(11)14/h2-5H,6H2,1H3,(H,13,14)

InChI Key

FUHQSEOSBHASCH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica carinata	Plant	KNApSAcK
Brassica napus L.ssp.rapifera	Plant	KNApSAcK
Brassica oleracea	LOTUS Database	35616633
Brassica oleracea var. botrytis	FooDB	KNAPSACK
Brassica oleracea var.botrytis	Plant	KNApSAcK
Brassica rapa	FooDB	KNAPSACK
Pseudomonas cichorii	LOTUS Database	35616633
Raphanus sativus	FooDB	KNAPSACK
Raphanus sativus subsp. longipinnatu	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Benzenoid
Meta-thiazoline
Carboxamide group
Lactam
Secondary carboxylic acid amide
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
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	2.05	ALOGPS
logP	2.76	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.65	ChemAxon
pKa (Strongest Basic)	3.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.39 m³·mol⁻¹	ChemAxon
Polarizability	25.27 Å³	ChemAxon
Number of Rings	3	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

HMDB0035974

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011345

KNApSAcK ID

Not Available

Chemspider ID

4930317

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6424827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Spirobrassinin (NP0047609)

MOL for NP0047609 (Spirobrassinin)

3D MOL for NP0047609 (Spirobrassinin)

3D SDF for NP0047609 (Spirobrassinin)

3D-SDF for NP0047609 (Spirobrassinin)

PDB for NP0047609 (Spirobrassinin)

3D PDB for NP0047609 (Spirobrassinin)

SMILES for NP0047609 (Spirobrassinin)

INCHI for NP0047609 (Spirobrassinin)

Structure for NP0047609 (Spirobrassinin)

3D Structure for NP0047609 (Spirobrassinin)