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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:11:14 UTC

Update Date

2023-02-21 17:17:52 UTC

HMDB ID

HMDB0012992

Secondary Accession Numbers

HMDB12992

Metabolite Identification

Common Name

Leukoaminochrome

Description

Leukoaminochrome, also known as 5,6-indolinediol or indoline-5,6-diol, 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. Leukoaminochrome is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Leukoaminochrome.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dihydro-5,6-dihydroxyindole	ChEBI
2-Descarboxy-cyclo-dopa	ChEBI
5,6-Dihydroxy-2,3-dihydroindole	ChEBI
5,6-Dihydroxyindoline	ChEBI
5,6-Indolinediol	ChEBI
56DHInn	ChEBI
Indoline-5,6-diol	ChEBI
Leucoaminochrome	HMDB

Chemical Formula

C₈H₉NO₂

Average Molecular Weight

151.1626

Monoisotopic Molecular Weight

151.063328537

IUPAC Name

2,3-dihydro-1H-indole-5,6-diol

Traditional Name

2,3-dihydro-1H-indole-5,6-diol

CAS Registry Number

29539-03-5

SMILES

OC1=C(O)C=C2NCCC2=C1

InChI Identifier

InChI=1S/C8H9NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h3-4,9-11H,1-2H2

InChI Key

VGSVNUGKHOVSPK-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
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
Azacycle
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechols (CHEBI:74683 )
indoles (CHEBI:74683 )

Ontology

Not Available

Endogenous (HMDB: HMDB0012992)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17270 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.5 g/L	ALOGPS
logP	1.36	ALOGPS
logP	0.88	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	5.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.52 m³·mol⁻¹	ChemAxon
Polarizability	15.45 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
DarkChem	[M+H]+	130.929	31661259
DarkChem	[M-H]-	127.515	31661259
DeepCCS	[M+H]+	135.585	30932474
DeepCCS	[M-H]-	132.581	30932474
DeepCCS	[M-2H]-	169.295	30932474
DeepCCS	[M+Na]+	144.832	30932474
AllCCS	[M+H]+	131.7	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	130.1	32859911
AllCCS	[M+HCOO]-	131.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leukoaminochrome	OC1=C(O)C=C2NCCC2=C1	2971.9	Standard polar	33892256
Leukoaminochrome	OC1=C(O)C=C2NCCC2=C1	1681.9	Standard non polar	33892256
Leukoaminochrome	OC1=C(O)C=C2NCCC2=C1	1724.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leukoaminochrome,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O)NCC2	1741.0	Semi standard non polar	33892256
Leukoaminochrome,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN2	1755.4	Semi standard non polar	33892256
Leukoaminochrome,1TMS,isomer #3	C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C21	1883.9	Semi standard non polar	33892256
Leukoaminochrome,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)NCC2	1828.5	Semi standard non polar	33892256
Leukoaminochrome,2TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)CC2	1844.9	Semi standard non polar	33892256
Leukoaminochrome,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN2[Si](C)(C)C	1856.3	Semi standard non polar	33892256
Leukoaminochrome,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)CC2	1890.8	Semi standard non polar	33892256
Leukoaminochrome,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)CC2	1883.9	Standard non polar	33892256
Leukoaminochrome,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)CC2	1875.4	Standard polar	33892256
Leukoaminochrome,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)NCC2	1985.6	Semi standard non polar	33892256
Leukoaminochrome,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN2	2004.8	Semi standard non polar	33892256
Leukoaminochrome,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C21	2140.5	Semi standard non polar	33892256
Leukoaminochrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)NCC2	2274.2	Semi standard non polar	33892256
Leukoaminochrome,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)CC2	2333.6	Semi standard non polar	33892256
Leukoaminochrome,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN2[Si](C)(C)C(C)(C)C	2344.7	Semi standard non polar	33892256
Leukoaminochrome,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)CC2	2577.5	Semi standard non polar	33892256
Leukoaminochrome,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)CC2	2584.2	Standard non polar	33892256
Leukoaminochrome,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)CC2	2304.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leukoaminochrome GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zmi-1900000000-25d2fbb7f811650a35c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukoaminochrome GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3190000000-f73a6d6c9c928f94d40a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukoaminochrome 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 - Leukoaminochrome 10V, Positive-QTOF	splash10-0udi-0900000000-ea5804ebafd462b893d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Positive-QTOF	splash10-0udi-0900000000-8aa2be80a64f5c67626f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Positive-QTOF	splash10-0pdm-9500000000-d533de78e8b5c0754db6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Negative-QTOF	splash10-0udi-0900000000-ff9a5c5e15b09c7c5a61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Negative-QTOF	splash10-0udi-0900000000-e7919fac3cd446c9d90d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Negative-QTOF	splash10-000x-9800000000-34dc5d16e4f5b5140900	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Positive-QTOF	splash10-0udi-0900000000-00ad05f28905520632a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Positive-QTOF	splash10-0udi-0900000000-a2c8811c0ab106aea8d4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Positive-QTOF	splash10-0006-9400000000-3226ed5ce190d3423414	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Negative-QTOF	splash10-0udi-0900000000-c294e68376c4342ea785	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Negative-QTOF	splash10-0udi-1900000000-a93220e742bef664f056	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Negative-QTOF	splash10-0007-8900000000-3468369d6ceabb8d2c2c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB029236

KNApSAcK ID

Not Available

Chemspider ID

129893

KEGG Compound ID

C17756

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

147311

PDB ID

Not Available

ChEBI ID

74683

Food Biomarker Ontology

Not Available

VMH ID

CE5665

MarkerDB ID

Not Available

Good Scents ID

rw1727211

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Leukoaminochrome (HMDB0012992)

MOL for HMDB0012992 (Leukoaminochrome)

3D MOL for HMDB0012992 (Leukoaminochrome)

3D SDF for HMDB0012992 (Leukoaminochrome)

3D-SDF for HMDB0012992 (Leukoaminochrome)

PDB for HMDB0012992 (Leukoaminochrome)

3D PDB for HMDB0012992 (Leukoaminochrome)

SMILES for HMDB0012992 (Leukoaminochrome)

INCHI for HMDB0012992 (Leukoaminochrome)

Structure for HMDB0012992 (Leukoaminochrome)

3D Structure for HMDB0012992 (Leukoaminochrome)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra