NP-MRD: Showing NP-Card for 3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde (NP0297985)

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Record Information

Version

2.0

Created at

2022-09-10 08:49:55 UTC

Updated at

2022-09-10 08:49:55 UTC

NP-MRD ID

NP0297985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

Description

Brassicanal B belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Brassicanal B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Brassicanal B has been detected, but not quantified in, brassicas. 3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde is found in Brassica rapa and Pseudomonas cichorii. This could make brassicanal b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310322D          

 16 18  0  0  0  0            999 V2000
    2.9708    3.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962    1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    2.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4519    0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942    1.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068    2.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132   -0.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669    3.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    1.4253    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO2S/c1-12(15)7-16-11-9(6-14)8-4-2-3-5-10(8)13(11)12/h2-6,15H,7H2,1H3

> <INCHI_KEY>
ZIEFIDANMCIAOW-UHFFFAOYSA-N

> <FORMULA>
C12H11NO2S

> <MOLECULAR_WEIGHT>
233.286

> <EXACT_MASS>
233.051049291

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.967352391407335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3-methyl-2H,3H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.9496213166666663

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.675156430196289

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8156865774321433

> <JCHEM_POLAR_SURFACE_AREA>
42.230000000000004

> <JCHEM_REFRACTIVITY>
65.0337

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-methyl-2H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.545   6.139   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.260   3.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.813   4.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.207   2.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.313   5.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   0.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.229   4.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.707   2.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.444   1.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.260   4.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.216   2.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.493   5.015   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.720   4.085   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       5.065  -0.583   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.485   6.179   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0       3.676   2.661   0.000  0.00  0.00           S+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   14                                                       
CONECT    7   12   16                                                       
CONECT    8    4    9   10                                                  
CONECT    9    6    8   11                                                  
CONECT   10    5    8   13                                                  
CONECT   11    9   13   16                                                  
CONECT   12    1    7   13   15                                             
CONECT   13   10   11   12                                                  
CONECT   14    6                                                            
CONECT   15   12                                                            
CONECT   16    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydro-3-hydroxy-3-methylthiazolo[3,2-a]indole-9-carboxaldehyde, 9ci	HMDB

Chemical Formula

C₁₂H₁₁NO₂S

Average Mass

233.2860 Da

Monoisotopic Mass

233.05105 Da

IUPAC Name

3-hydroxy-3-methyl-2H,3H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

Traditional Name

3-hydroxy-3-methyl-2H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12

InChI Identifier

InChI=1S/C12H11NO2S/c1-12(15)7-16-11-9(6-14)8-4-2-3-5-10(8)13(11)12/h2-6,15H,7H2,1H3

InChI Key

ZIEFIDANMCIAOW-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
Brassica rapa	LOTUS Database	35616633
Pseudomonas cichorii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aryl thioether
Alkylarylthioether
Aryl-aldehyde
Substituted pyrrole
Vinylogous thioester
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous amide
Alkanolamine
Thioether
Azacycle
Aldehyde
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
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	1.74	ALOGPS
logP	1.95	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.03 m³·mol⁻¹	ChemAxon
Polarizability	23.97 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

HMDB0038592

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017982

KNApSAcK ID

Not Available

Chemspider ID

326803

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

368117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde (NP0297985)

MOL for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

3D MOL for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

3D SDF for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

3D-SDF for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

PDB for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

3D PDB for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

SMILES for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

INCHI for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

Structure for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)

3D Structure for NP0297985 (3-hydroxy-3-methyl-2h-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde)