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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:23:43 UTC

Update Date

2021-09-26 23:10:36 UTC

HMDB ID

HMDB0255614

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ninhydrin

Description

ninhydrin belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups. ninhydrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Ninhydrin is also used in amino acid analysis of proteins. This approach was successfully used to reveal that some ammonium oxidizing bacteria, also called nitrifying bacteria use urea as a carbon source in soil. Also, certain amino acid chains are degraded. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ninhydrin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ninhydrin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.121   2.087   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.121   3.599   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5    9   10                                                  
CONECT    8    6    9   11                                                  
CONECT    9    7    8   12   13                                             
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2,3-Indantrione monohydrate	ChEBI
1,2,3-Indantrione, 2-hydrate	ChEBI
2,2-Dihydroxy-1,3-indandione	ChEBI
2,2-Dihydroxyindane-1,3-dione	ChEBI
Triketohydrindene hydrate	ChEBI
1,2,3-Indantrione monohydric acid	Generator
1,2,3-Indantrione, 2-hydric acid	Generator
Triketohydrindene hydric acid	Generator
Indantrione monohydrate	MeSH
Monohydrate, indantrione	MeSH
Ninhydrin	MeSH

Chemical Formula

C₉H₆O₄

Average Molecular Weight

178.143

Monoisotopic Molecular Weight

178.026608673

IUPAC Name

2,2-dihydroxy-2,3-dihydro-1H-indene-1,3-dione

Traditional Name

ninhydrin

CAS Registry Number

Not Available

SMILES

OC1(O)C(=O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H

InChI Key

FEMOMIGRRWSMCU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Indanedione
Aryl alkyl ketone
Aryl ketone
Ketone
Carbonyl hydrate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ketone (CHEBI:86374 )
beta-diketone (CHEBI:86374 )
indanones (CHEBI:86374 )
ketone hydrate (CHEBI:86374 )
a small molecule (CPD-9188 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	0.84	ALOGPS
logP	0.45	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.44 m³·mol⁻¹	ChemAxon
Polarizability	16.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	134.986	30932474
DeepCCS	[M-H]-	131.527	30932474
DeepCCS	[M-2H]-	168.694	30932474
DeepCCS	[M+Na]+	144.233	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	132.9	32859911
AllCCS	[M+Na-2H]-	133.3	32859911
AllCCS	[M+HCOO]-	133.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ninhydrin	OC1(O)C(=O)C2=CC=CC=C2C1=O	2450.2	Standard polar	33892256
Ninhydrin	OC1(O)C(=O)C2=CC=CC=C2C1=O	1426.6	Standard non polar	33892256
Ninhydrin	OC1(O)C(=O)C2=CC=CC=C2C1=O	1517.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ninhydrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugi-0900000000-a0a48a02312cbe3d4bd9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ninhydrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ninhydrin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ninhydrin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ninhydrin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ninhydrin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	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 - Ninhydrin 10V, Positive-QTOF	splash10-004i-0900000000-602bff3cc7435a373fd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ninhydrin 20V, Positive-QTOF	splash10-004i-0900000000-2f1636985d27f0855522	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ninhydrin 40V, Positive-QTOF	splash10-0nmi-2900000000-283bd63718dae8faa5e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ninhydrin 10V, Negative-QTOF	splash10-004i-0900000000-8756592ab5426261cb8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ninhydrin 20V, Negative-QTOF	splash10-004i-0900000000-42ca8bb47a47e7c2a050	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ninhydrin 40V, Negative-QTOF	splash10-0ufr-1900000000-df9172fc149290517005	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-9188

BiGG ID

Not Available

Wikipedia Link

Ninhydrin

METLIN ID

Not Available

PubChem Compound

10236

PDB ID

Not Available

ChEBI ID

86374

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Ninhydrin (HMDB0255614)

MOL for HMDB0255614 (Ninhydrin)

3D MOL for HMDB0255614 (Ninhydrin)

3D SDF for HMDB0255614 (Ninhydrin)

3D-SDF for HMDB0255614 (Ninhydrin)

PDB for HMDB0255614 (Ninhydrin)

3D PDB for HMDB0255614 (Ninhydrin)

SMILES for HMDB0255614 (Ninhydrin)

INCHI for HMDB0255614 (Ninhydrin)

Structure for HMDB0255614 (Ninhydrin)

3D Structure for HMDB0255614 (Ninhydrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra