NP-MRD: Showing NP-Card for 3'-hydroxy-1'h-[2,2'-biindol]-3-one (NP0233528)

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Record Information

Version

2.0

Created at

2022-09-06 15:09:52 UTC

Updated at

2022-09-06 15:09:52 UTC

NP-MRD ID

NP0233528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-hydroxy-1'h-[2,2'-biindol]-3-one

Description

INDIGO, also known as indigo carmine or indigotin, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 3'-hydroxy-1'h-[2,2'-biindol]-3-one is found in Couroupita guianensis and Isatis tinctoria. 3'-hydroxy-1'h-[2,2'-biindol]-3-one was first documented in 2022 (PMID: 36076043). Based on a literature review a small amount of articles have been published on INDIGO (PMID: 36077972) (PMID: 36077196) (PMID: 36065773) (PMID: 36060126).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
    0.9920   -2.4066   -0.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5068   -1.2589   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704   -0.0219    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6979    0.0847    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508   -0.9556    0.1257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8220   -0.4848    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -1.1117    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2392   -0.4297    0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1798    0.9346    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9417    1.5773    0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7823    0.8728    0.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    1.2232    0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    2.5165    0.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166    0.9399    0.2176 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9522    0.4650    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2004    1.0609    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576    0.3012   -0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -1.0520   -0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0325   -1.6797   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -0.9039   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249   -1.9646   -0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0866   -2.1832    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2138   -0.9306    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0898    1.5080    0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115    2.6513    0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533    2.6734    0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    2.1337    0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3027    0.8060   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547   -1.6219   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -2.7432   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4  3  1  0
  3 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
  2  1  2  0
 11 12  1  0
  2  3  1  0
 11  6  1  0
 20 15  1  0
 13 26  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END


  Mrv1652309062217092D          

 20 23  0  0  0  0            999 V2000
    1.9981   -4.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530   -3.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -2.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431   -2.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -3.2954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -3.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -3.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -3.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -1.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530   -1.9605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521   -1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4666   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4666   -3.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521   -3.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -3.0404    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(NC2=CC=CC=C12)C1=NC2=CC=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17,19H

> <INCHI_KEY>
QQILFGKZUJYXGS-UHFFFAOYSA-N

> <FORMULA>
C16H10N2O2

> <MOLECULAR_WEIGHT>
262.268

> <EXACT_MASS>
262.07422757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
28.01925065664836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3'-hydroxy-1'H,3H-[2,2'-biindole]-3-one

> <JCHEM_LOGP>
3.148437075666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.040734809220655

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.958035211977965

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3946375719832385

> <JCHEM_POLAR_SURFACE_AREA>
65.44999999999999

> <JCHEM_REFRACTIVITY>
77.70530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3'-hydroxy-1'H-[2,2'-biindole]-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       3.730  -7.616   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.206  -6.151   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.300  -4.905   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.760  -4.905   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.855  -6.151   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.609  -5.675   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.943  -6.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.277  -5.675   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.277  -4.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.943  -3.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.609  -4.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.855  -3.660   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.331  -2.195   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       4.206  -3.660   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.670  -4.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.004  -3.365   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.338  -4.135   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.338  -5.675   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.004  -6.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.670  -5.675   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15    2                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
FD And C blue no. 2	MeSH
Indigo carmine	MeSH
Indigo disulfonate	MeSH
Indigotindisulfonate	MeSH
Soluble indigo blue	MeSH
(delta-2,2'-Biindole)-3,3'-dione	MeSH
D And C blue no. 6	MeSH
Indigo blue, soluble	MeSH
Indigotindisulfonic acid	MeSH
Indigotin	MeSH
Indigo blue	MeSH
Indigotindisulfonate sodium	MeSH
2-(1,3-Dihydro-3-oxo-5-sulphO-2H-indol-2-ylidene)-3- oxoindoline-5-sulphonic acid	MeSH
Carmine, indigo	MeSH

Chemical Formula

C₁₆H₁₀N₂O₂

Average Mass

262.2680 Da

Monoisotopic Mass

262.07423 Da

IUPAC Name

3'-hydroxy-1'H,3H-[2,2'-biindole]-3-one

Traditional Name

3'-hydroxy-1'H-[2,2'-biindole]-3-one

CAS Registry Number

Not Available

SMILES

OC1=C(NC2=CC=CC=C12)C1=NC2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17,19H

InChI Key

QQILFGKZUJYXGS-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
Couroupita guianensis	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
Indole
Aryl ketone
Benzenoid
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Ketimine
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Imine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	3.15	ChemAxon
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.71 m³·mol⁻¹	ChemAxon
Polarizability	28.02 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

C00000126

Chemspider ID

23131661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indian Initiative in Gravitational-wave Observations

METLIN ID

Not Available

PubChem Compound

10215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang S, Tang X, Yu L, Hong S, Liu J, Xu B, Liu R, Guo Y, Xu L: Colorimetric assay of phosphate using a multicopper laccase-like nanozyme. Mikrochim Acta. 2022 Sep 8;189(10):378. doi: 10.1007/s00604-022-05476-2. [PubMed:36076043 ]
Candido MV, Syrja P, Kilpinen S, Meisner S, Hanifeh M, Spillmann T: Can Chromoendoscopy Improve the Early Diagnosis of Gastric Carcinoma in Dogs? Animals (Basel). 2022 Aug 31;12(17). pii: ani12172253. doi: 10.3390/ani12172253. [PubMed:36077972 ]
Ainiwaer A, Liang Y, Ye X, Gao R: Characterization of a Novel Fe(2+) Activated Non-Blue Laccase from Methylobacterium extorquens. Int J Mol Sci. 2022 Aug 29;23(17). pii: ijms23179804. doi: 10.3390/ijms23179804. [PubMed:36077196 ]
Cale R, Pereira AR, Ferreira F, Alegria S, Morgado G, Martins C, Ferreira M, Gomes A, Judas T, Gonzalez F, Lohmann C, Repolho D, Santos P, Pereira E, Loureiro MJ, Pereira H: Continuous Aspiration Mechanical Thrombectomy for the management of intermediate- and high-risk pulmonary embolism: Data from the first cohort in Portugal. Rev Port Cardiol. 2022 Jul;41(7):533-545. doi: 10.1016/j.repc.2021.04.009. Epub 2022 May 27. [PubMed:36065773 ]
Lu Q, Li J, Ding P, Mao T, Shi L, Sun Z, Tan X, Jiang H, Dong J, Li Y, Yang X, Shi R: Qingchang Wenzhong Decoction Alleviates DSS-Induced Inflammatory Bowel Disease by Inhibiting M1 Macrophage Polarization In Vitro and In Vivo. Biomed Res Int. 2022 Aug 25;2022:9427076. doi: 10.1155/2022/9427076. eCollection 2022. [PubMed:36060126 ]
LOTUS database [Link]

Showing NP-Card for 3'-hydroxy-1'h-[2,2'-biindol]-3-one (NP0233528)

MOL for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

3D MOL for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

3D SDF for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

3D-SDF for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

PDB for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

3D PDB for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

SMILES for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

INCHI for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

Structure for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)

3D Structure for NP0233528 (3'-hydroxy-1'h-[2,2'-biindol]-3-one)