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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:11:56 UTC

Update Date

2021-09-14 15:48:20 UTC

HMDB ID

HMDB0013029

Secondary Accession Numbers

HMDB13029

Metabolite Identification

Common Name

Noradrenochrome o-semiquinone

Description

Noradrenochrome o-semiquinone is a intermediate metabolite in the reduction of noradrenochrome. Noradrenochrome is an aminochrome and is closely related to adrenochrome and dopaminochrome. This compound is present in human brain, induces a combination of neurotoxic and mind-mood altering effect, and is therapeutic for the treatment of schizophrenia.

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      19.893 -40.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      21.226 -40.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.560 -40.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.894 -40.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.359 -40.477   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      25.835 -41.941   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      26.263 -39.231   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      25.359 -37.985   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      23.894 -38.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.560 -37.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.226 -38.461   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      19.893 -37.691   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    2   10   12                                                  
CONECT   12   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
NAdcSq	HMDB

Chemical Formula

C₈H₈NO₃

Average Molecular Weight

166.154

Monoisotopic Molecular Weight

166.050418127

IUPAC Name

(3,6-dihydroxy-2,3-dihydro-1H-indol-5-yl)oxidanyl

Traditional Name

3,6-dihydroxy-2,3-dihydro-1H-indol-5-yloxidanyl

CAS Registry Number

Not Available

SMILES

[O]C1=C(O)C=C2NCC(O)C2=C1

InChI Identifier

InChI=1S/C8H8NO3/c10-6-1-4-5(2-7(6)11)9-3-8(4)12/h1-2,8-9,11-12H,3H2

InChI Key

OHRTXTGCGQYCMB-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
Secondary aliphatic/aromatic amine
Aralkylamine
Benzenoid
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0013029)

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	31.4 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-0.051	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	0.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	55.28 m³·mol⁻¹	ChemAxon
Polarizability	15.95 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.778	31661259
DarkChem	[M-H]-	134.559	31661259
DeepCCS	[M+H]+	138.122	30932474
DeepCCS	[M-H]-	135.333	30932474
DeepCCS	[M-2H]-	171.366	30932474
DeepCCS	[M+Na]+	146.799	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.2	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.4	32859911
AllCCS	[M+HCOO]-	134.2	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Noradrenochrome o-semiquinone,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1[O])C(O)CN2	1910.5	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,1TMS,isomer #2	C[Si](C)(C)OC1CNC2=CC(O)=C([O])C=C21	1918.8	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,1TMS,isomer #3	C[Si](C)(C)N1CC(O)C2=CC([O])=C(O)C=C21	1928.4	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C)CN2	1924.0	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,2TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1[O])C(O)CN2[Si](C)(C)C	1943.7	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,2TMS,isomer #3	C[Si](C)(C)OC1CN([Si](C)(C)C)C2=CC(O)=C([O])C=C21	1930.5	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C)CN2[Si](C)(C)C	1982.0	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C)CN2[Si](C)(C)C	1970.4	Standard non polar	33892256
Noradrenochrome o-semiquinone,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C)CN2[Si](C)(C)C	2027.9	Standard polar	33892256
Noradrenochrome o-semiquinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1[O])C(O)CN2	2171.2	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1CNC2=CC(O)=C([O])C=C21	2173.7	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC(O)C2=CC([O])=C(O)C=C21	2201.8	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C(C)(C)C)CN2	2392.3	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1[O])C(O)CN2[Si](C)(C)C(C)(C)C	2462.1	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CN([Si](C)(C)C(C)(C)C)C2=CC(O)=C([O])C=C21	2445.0	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2663.9	Semi standard non polar	33892256
Noradrenochrome o-semiquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2667.8	Standard non polar	33892256
Noradrenochrome o-semiquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1[O])C(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2432.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome o-semiquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-8c43500ea7ad035e84c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome o-semiquinone GC-MS (2 TMS) - 70eV, Positive	splash10-0036-6190000000-042fd065822cdad7a25f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome o-semiquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noradrenochrome o-semiquinone 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 o-semiquinone 10V, Positive-QTOF	splash10-0udj-0900000000-727e63c3a12e055c4092	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 20V, Positive-QTOF	splash10-0udi-0900000000-bf7a0c07bb3bdf7987c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 40V, Positive-QTOF	splash10-00di-2900000000-9f914609b7cd48732518	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 10V, Negative-QTOF	splash10-00kb-0900000000-aa31b1ebe2b3203de7d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 20V, Negative-QTOF	splash10-0002-0900000000-b33e077d45ffa1d292dc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 40V, Negative-QTOF	splash10-05fu-5900000000-853e6a60797daeb9630f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 10V, Positive-QTOF	splash10-0udi-0900000000-0f1669ff1a91e402f4b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 20V, Positive-QTOF	splash10-0udi-0900000000-fde0f163864b73b52009	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noradrenochrome o-semiquinone 40V, Positive-QTOF	splash10-0089-3900000000-b9a9d31f1075d263dc3f	2021-09-25	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

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

FDB029255

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for Noradrenochrome o-semiquinone (HMDB0013029)

MOL for HMDB0013029 (Noradrenochrome o-semiquinone)

3D MOL for HMDB0013029 (Noradrenochrome o-semiquinone)

3D SDF for HMDB0013029 (Noradrenochrome o-semiquinone)

3D-SDF for HMDB0013029 (Noradrenochrome o-semiquinone)

PDB for HMDB0013029 (Noradrenochrome o-semiquinone)

3D PDB for HMDB0013029 (Noradrenochrome o-semiquinone)

SMILES for HMDB0013029 (Noradrenochrome o-semiquinone)

INCHI for HMDB0013029 (Noradrenochrome o-semiquinone)

Structure for HMDB0013029 (Noradrenochrome o-semiquinone)

3D Structure for HMDB0013029 (Noradrenochrome o-semiquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra