NP-MRD: Showing NP-Card for 1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one (NP0213659)

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Record Information

Version

2.0

Created at

2022-09-05 12:42:42 UTC

Updated at

2022-09-05 12:42:43 UTC

NP-MRD ID

NP0213659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one

Description

2H-Indol-2-one, 4,6-dibromo-1,3-dihydro-3-hydroxy-3-(2-oxopropyl)- 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. 1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one is found in Amathia convoluta. 2H-Indol-2-one, 4,6-dibromo-1,3-dihydro-3-hydroxy-3-(2-oxopropyl)- is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514252D          

 17 18  0  0  0  0            999 V2000
   -0.2902   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -3.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  5 17  1  0  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC1(O)C(=O)NC2=CC(Br)=CC(Br)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H9Br2NO3/c1-5(15)4-11(17)9-7(13)2-6(12)3-8(9)14-10(11)16/h2-3,17H,4H2,1H3,(H,14,16)

> <INCHI_KEY>
UCZPZZBCCIUPSH-UHFFFAOYSA-N

> <FORMULA>
C11H9Br2NO3

> <MOLECULAR_WEIGHT>
363.005

> <EXACT_MASS>
360.894919

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
27.194865733775558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dibromo-3-hydroxy-3-(2-oxopropyl)-2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.014976475666667

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.339624710772235

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.339401765416952

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307448753752532

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
70.4685

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dibromo-3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.542  -5.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.792  -4.859   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.126  -5.629   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.792  -3.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.752  -3.956   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       7.591   0.237   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       4.924  -4.383   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Convolutamydine a	MeSH

Chemical Formula

C₁₁H₉Br₂NO₃

Average Mass

363.0050 Da

Monoisotopic Mass

360.89492 Da

IUPAC Name

4,6-dibromo-3-hydroxy-3-(2-oxopropyl)-2,3-dihydro-1H-indol-2-one

Traditional Name

4,6-dibromo-3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)CC1(O)C(=O)NC2=CC(Br)=CC(Br)=C12

InChI Identifier

InChI=1S/C11H9Br2NO3/c1-5(15)4-11(17)9-7(13)2-6(12)3-8(9)14-10(11)16/h2-3,17H,4H2,1H3,(H,14,16)

InChI Key

UCZPZZBCCIUPSH-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
Amathia convoluta	LOTUS Database	35616633

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
Aryl bromide
Aryl halide
Beta-hydroxy ketone
Benzenoid
Tertiary alcohol
Carboxamide group
Secondary carboxylic acid amide
Ketone
Lactam
Azacycle
Carboxylic acid derivative
Alcohol
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	2.06	ALOGPS
logP	2.01	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.47 m³·mol⁻¹	ChemAxon
Polarizability	27.19 Å³	ChemAxon
Number of Rings	2	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

10067245

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one (NP0213659)

MOL for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

3D MOL for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

3D SDF for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

3D-SDF for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

PDB for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

3D PDB for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

SMILES for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

INCHI for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

Structure for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)

3D Structure for NP0213659 (1-(4,6-dibromo-2,3-dihydroxyindol-3-yl)propan-2-one)