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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:11:57 UTC

Update Date

2023-02-21 17:17:53 UTC

HMDB ID

HMDB0013030

Secondary Accession Numbers

HMDB13030

Metabolite Identification

Common Name

Noradrenochrome

Description

Noradrenochrome belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on Noradrenochrome.

Structure

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

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      27.612 -39.267   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      27.933 -37.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.340 -37.134   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      29.178 -35.603   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      27.672 -35.282   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.902 -33.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.362 -33.949   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.592 -32.615   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.592 -35.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      23.052 -35.282   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      25.362 -36.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.902 -36.616   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12    2    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6-dioxo-2,3,5,6-tetrahydro-3-Hydroxyindole	HMDB
5,6-dioxo-2,3,5,6-tetrahydro-3-Indolol	HMDB
AdChr	HMDB
Noradrenochrome O-quinone	HMDB
Noradrenochrome oxidised	HMDB
Cyclized norepinephrine ortho-quinone	MeSH

Chemical Formula

C₈H₇NO₃

Average Molecular Weight

165.1461

Monoisotopic Molecular Weight

165.042593095

IUPAC Name

3-hydroxy-3,5,6,7-tetrahydro-2H-indole-5,6-dione

Traditional Name

3-hydroxy-3,7-dihydro-2H-indole-5,6-dione

CAS Registry Number

490-89-1

SMILES

OC1CN=C2CC(=O)C(=O)C=C12

InChI Identifier

InChI=1S/C8H7NO3/c10-6-1-4-5(2-7(6)11)9-3-8(4)12/h1,8,12H,2-3H2

InChI Key

PTQNKGWWIYGAAE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Cyclohexenone
Pyrroline
Ketimine
Ketone
Secondary alcohol
Cyclic ketone
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Imine
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0013030)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.33 g/L	ALOGPS
logP	-0.57	ALOGPS
logP	0.26	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	4.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.73 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.54 m³·mol⁻¹	ChemAxon
Polarizability	15.37 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]+	137.03	31661259
DarkChem	[M-H]-	131.094	31661259
DeepCCS	[M-2H]-	167.257	30932474
DeepCCS	[M+Na]+	142.796	30932474
AllCCS	[M+H]+	134.6	32859911
AllCCS	[M+H-H2O]+	130.1	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.1	32859911
AllCCS	[M-H]-	132.1	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	133.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.7 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1889 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	67.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	873.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	313.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	260.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	316.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	160.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	660.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	129.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	862.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	512.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	271.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	141.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Noradrenochrome	OC1CN=C2CC(=O)C(=O)C=C12	2942.8	Standard polar	33892256
Noradrenochrome	OC1CN=C2CC(=O)C(=O)C=C12	1743.1	Standard non polar	33892256
Noradrenochrome	OC1CN=C2CC(=O)C(=O)C=C12	1572.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Noradrenochrome,1TMS,isomer #1	C[Si](C)(C)OC1CN=C2CC(=O)C(=O)C=C21	1841.3	Semi standard non polar	33892256
Noradrenochrome,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=NCC(O)C2=CC1=O	1913.4	Semi standard non polar	33892256
Noradrenochrome,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=NCC(O[Si](C)(C)C)C2=CC1=O	1966.6	Semi standard non polar	33892256
Noradrenochrome,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=NCC(O[Si](C)(C)C)C2=CC1=O	1723.3	Standard non polar	33892256
Noradrenochrome,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=NCC(O[Si](C)(C)C)C2=CC1=O	3042.6	Standard polar	33892256
Noradrenochrome,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CN=C2CC(=O)C(=O)C=C21	2072.3	Semi standard non polar	33892256
Noradrenochrome,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=NCC(O)C2=CC1=O	2156.8	Semi standard non polar	33892256
Noradrenochrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=NCC(O[Si](C)(C)C(C)(C)C)C2=CC1=O	2434.8	Semi standard non polar	33892256
Noradrenochrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=NCC(O[Si](C)(C)C(C)(C)C)C2=CC1=O	2135.7	Standard non polar	33892256
Noradrenochrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=NCC(O[Si](C)(C)C(C)(C)C)C2=CC1=O	3306.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fs-8900000000-b8bf972fa7b384c177cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9640000000-94e5729c119b4f33b4fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome 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 - Noradrenochrome 10V, Positive-QTOF	splash10-014i-0900000000-54a88fc5ae849b3139fc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 20V, Positive-QTOF	splash10-00kb-0900000000-02b253c9f61c98665071	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 40V, Positive-QTOF	splash10-0aou-9400000000-78972a8172f41ceb21b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 10V, Negative-QTOF	splash10-03di-0900000000-f11f49deb557d5d11503	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 20V, Negative-QTOF	splash10-03di-0900000000-ac348f2387aeffb9e929	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 40V, Negative-QTOF	splash10-0a59-4900000000-1ff5a9799f5463f14220	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 10V, Negative-QTOF	splash10-03di-0900000000-65490e650f013cfe115e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 20V, Negative-QTOF	splash10-03di-0900000000-b87e3a72f8a872d73e25	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 40V, Negative-QTOF	splash10-0ac3-2900000000-5912cbe5d2d9cc0a8324	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 10V, Positive-QTOF	splash10-014i-0900000000-9505c7726be7ea1b51d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 20V, Positive-QTOF	splash10-014i-0900000000-d1deaf55837d69fc7853	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome 40V, Positive-QTOF	splash10-052f-9500000000-d0f6a26748f4650d9c0d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB029256

KNApSAcK ID

Not Available

Chemspider ID

8351782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10176277

PDB ID

Not Available

ChEBI ID

173732

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

Not Available

Enzymes

Enzyme Details

1. Glutathione S-transferase theta-2

General function:: Posttranslational modification, protein turnover, chaperones
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a sulfatase activity.
Gene Name:: GSTT2
Uniprot ID:: P0CG29
Molecular weight:: Not Available

Showing metabocard for Noradrenochrome (HMDB0013030)

MOL for HMDB0013030 (Noradrenochrome)

3D MOL for HMDB0013030 (Noradrenochrome)

3D SDF for HMDB0013030 (Noradrenochrome)

3D-SDF for HMDB0013030 (Noradrenochrome)

PDB for HMDB0013030 (Noradrenochrome)

3D PDB for HMDB0013030 (Noradrenochrome)

SMILES for HMDB0013030 (Noradrenochrome)

INCHI for HMDB0013030 (Noradrenochrome)

Structure for HMDB0013030 (Noradrenochrome)

3D Structure for HMDB0013030 (Noradrenochrome)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes