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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:01:55 UTC

Update Date

2022-03-07 02:54:43 UTC

HMDB ID

HMDB0035974

Secondary Accession Numbers

HMDB35974

Metabolite Identification

Common Name

(S)-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 has been detected, but not quantified in, a few different foods, such as cauliflowers (Brassica oleracea var. botrytis), chinese cabbages (Brassica rapa), and radishes (Raphanus sativus). This could make (S)-spirobrassinin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (S)-Spirobrassinin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0035974

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0035974
HETATM    1  C1  UNL     1      -4.961   0.175  -0.315  1.00  0.00           C  
HETATM    2  S1  UNL     1      -3.889  -0.173   1.103  1.00  0.00           S  
HETATM    3  C2  UNL     1      -2.289  -0.651   0.499  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.919  -0.740  -0.688  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.634  -1.127  -1.009  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.317  -1.021   0.137  1.00  0.00           C  
HETATM    7  S2  UNL     1      -0.886  -1.093   1.509  1.00  0.00           S  
HETATM    8  C5  UNL     1       1.230  -2.152   0.132  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.910  -3.361   0.116  1.00  0.00           O  
HETATM   10  N2  UNL     1       2.550  -1.626   0.147  1.00  0.00           N  
HETATM   11  C6  UNL     1       2.452  -0.208   0.162  1.00  0.00           C  
HETATM   12  C7  UNL     1       3.434   0.790   0.180  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.123   2.130   0.192  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.789   2.477   0.185  1.00  0.00           C  
HETATM   15  C10 UNL     1       0.794   1.524   0.168  1.00  0.00           C  
HETATM   16  C11 UNL     1       1.129   0.182   0.156  1.00  0.00           C  
HETATM   17  H1  UNL     1      -6.035   0.055  -0.068  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.801   1.245  -0.639  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.656  -0.511  -1.131  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.248  -0.404  -1.789  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.538  -2.124  -1.499  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.465  -2.167   0.148  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.445   0.467   0.184  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.897   2.902   0.206  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.567   3.548   0.195  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.246   1.865   0.163  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4    7
CONECT    4    5
CONECT    5    6   20   21
CONECT    6    7    8   16
CONECT    8    9    9   10
CONECT   10   11   22
CONECT   11   12   12   16
CONECT   12   13   23
CONECT   13   14   14   24
CONECT   14   15   25
CONECT   15   16   16   26
END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₁H₁₀N₂OS₂

Average Molecular Weight

250.34

Monoisotopic Molecular Weight

250.023454332

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

Not Available

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035974)
Cytoplasm (HMDB: HMDB0035974)

Brassicas (FooDB: FOOD00857)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.62	31661259
DarkChem	[M-H]-	151.565	31661259
DeepCCS	[M+H]+	153.388	30932474
DeepCCS	[M-H]-	151.03	30932474
DeepCCS	[M-2H]-	183.916	30932474
DeepCCS	[M+Na]+	159.481	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	147.9	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	154.8	32859911
AllCCS	[M+HCOO]-	154.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Spirobrassinin	CSC1=NCC2(S1)C(=O)NC1=C2C=CC=C1	3581.8	Standard polar	33892256
(S)-Spirobrassinin	CSC1=NCC2(S1)C(=O)NC1=C2C=CC=C1	2263.0	Standard non polar	33892256
(S)-Spirobrassinin	CSC1=NCC2(S1)C(=O)NC1=C2C=CC=C1	2453.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Spirobrassinin,1TMS,isomer #1	CSC1=NCC2(S1)C(=O)N([Si](C)(C)C)C1=CC=CC=C12	2306.8	Semi standard non polar	33892256
(S)-Spirobrassinin,1TMS,isomer #1	CSC1=NCC2(S1)C(=O)N([Si](C)(C)C)C1=CC=CC=C12	2125.3	Standard non polar	33892256
(S)-Spirobrassinin,1TBDMS,isomer #1	CSC1=NCC2(S1)C(=O)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	2505.9	Semi standard non polar	33892256
(S)-Spirobrassinin,1TBDMS,isomer #1	CSC1=NCC2(S1)C(=O)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	2398.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Spirobrassinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00wd-5950000000-0b8b28ca5a0e76934e0e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Spirobrassinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 10V, Positive-QTOF	splash10-0udi-0090000000-d4504525b2b727e0313b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 20V, Positive-QTOF	splash10-0udi-0090000000-b4b1841b96a6a93db832	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 40V, Positive-QTOF	splash10-0pc4-8390000000-d1fdefa8ba4fbd6f5bf3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 10V, Negative-QTOF	splash10-0002-1090000000-280fd59a9a47e60da2d3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 20V, Negative-QTOF	splash10-0006-9010000000-338824f80fb01eb139a5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 40V, Negative-QTOF	splash10-0006-9000000000-9d5cd4d3db0eb6012c2e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 10V, Negative-QTOF	splash10-0002-0090000000-dcd408d8704a3e2b8066	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 20V, Negative-QTOF	splash10-0f6t-0090000000-27bd4a3ce0320a340ac5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 40V, Negative-QTOF	splash10-0006-9210000000-a4982cccbed7ba56d941	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 10V, Positive-QTOF	splash10-0udi-0090000000-1043d01fd652b4399f71	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 20V, Positive-QTOF	splash10-0udi-0090000000-2bfd726e7b86f2c9bb6a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Spirobrassinin 40V, Positive-QTOF	splash10-05fu-7950000000-b2f4cc1dbff820392508	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (S)-Spirobrassinin (HMDB0035974)

MOL for HMDB0035974 ((S)-Spirobrassinin)

3D MOL for HMDB0035974 ((S)-Spirobrassinin)

3D SDF for HMDB0035974 ((S)-Spirobrassinin)

3D-SDF for HMDB0035974 ((S)-Spirobrassinin)

PDB for HMDB0035974 ((S)-Spirobrassinin)

3D PDB for HMDB0035974 ((S)-Spirobrassinin)

SMILES for HMDB0035974 ((S)-Spirobrassinin)

INCHI for HMDB0035974 ((S)-Spirobrassinin)

Structure for HMDB0035974 ((S)-Spirobrassinin)

3D Structure for HMDB0035974 ((S)-Spirobrassinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra