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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

Detected and Quantified

Creation Date

2006-08-13 10:48:49 UTC

Update Date

2023-02-21 17:16:55 UTC

HMDB ID

HMDB0004096

Secondary Accession Numbers

HMDB04096

Metabolite Identification

Common Name

5-Methoxyindoleacetate

Description

5-Methoxyindoleacetate, also known as 5-methoxy-IAA or 5-MIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Methoxyindoleacetic acid is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946 ). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428 ).

Structure

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


  Mrv1652302102019392D          

 15 16  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3115 9997.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.617910000.1439    0.0000 O   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  2  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
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004096

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC=C2CC(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)

> <INCHI_KEY>
COCNDHOPIHDTHK-UHFFFAOYSA-N

> <FORMULA>
C11H11NO3

> <MOLECULAR_WEIGHT>
205.2099

> <EXACT_MASS>
205.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.72947019001754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-methoxy-1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.5520848326666667

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.518144509124706

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.296105404282163

> <JCHEM_PKA_STRONGEST_BASIC>
-4.830624015522234

> <JCHEM_POLAR_SURFACE_AREA>
62.32

> <JCHEM_REFRACTIVITY>
54.9153

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxyindole-3-acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8661.2888661.519   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8659.7818661.199   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8667.8208666.935   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11                                                            
CONECT   13    3   14                                                       
CONECT   14   13                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0004096
HETATM    1  C1  UNL     1      -3.658   1.842  -1.035  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.375   1.349  -1.281  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.646   0.609  -0.367  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.151   0.311   0.875  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.381  -0.434   1.754  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.116  -0.908   1.461  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.821  -1.635   2.108  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.892  -1.794   1.299  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.630  -1.154   0.113  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.492  -1.030  -1.110  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.065   0.323  -1.078  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.718   0.700  -0.082  1.00  0.00           O  
HETATM   13  O3  UNL     1       2.890   1.187  -2.133  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.353  -0.580   0.191  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.373   0.155  -0.711  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.237   1.097  -0.446  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.706   2.815  -0.517  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.199   1.983  -2.011  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.154   0.659   1.179  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.796  -0.665   2.723  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.736  -2.011   3.067  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.804  -2.326   1.522  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.244  -1.851  -1.149  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.841  -1.119  -2.028  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.264   2.103  -2.243  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.042   0.372  -1.671  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   19
CONECT    5    6    6   20
CONECT    6    7   14
CONECT    7    8   21
CONECT    8    9    9   22
CONECT    9   10   14
CONECT   10   11   23   24
CONECT   11   12   12   13
CONECT   13   25
CONECT   14   15   15
CONECT   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(5-Methoxy-1H-indol-3-yl)ethanoic acid	ChEBI
2-(5-Methoxyindole-3-yl)acetic acid	ChEBI
5-Methoxyindol-3-ylacetic acid	ChEBI
5-Methoxyindoleacetic acid	ChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanoate	Generator
2-(5-Methoxyindole-3-yl)acetate	Generator
5-Methoxyindol-3-ylacetate	Generator
5-Methoxyindole-3-acetate	HMDB
5-Methoxyindole-3-acetic acid	HMDB, MeSH
Methoxyindoleacetate	HMDB
Methoxyindoleacetic acid	HMDB
5-Methoxy-1H-indole-3-acetic acid	HMDB
(5-Methoxy-1H-indol-3-yl)acetic acid	HMDB
2-(5-Methoxy-1H-indol-3-yl)acetic acid	HMDB
2-(5-Methoxy-3-indolyl)acetic acid	HMDB
5-Methoxy-3-indoleacetic acid	HMDB
5-Methoxy-3-indolylacetic acid	HMDB
5-Methoxy-IAA	HMDB
5-Methyloxyindole-3-acetic acid	HMDB
5-MIAA	HMDB

Chemical Formula

C₁₁H₁₁NO₃

Average Molecular Weight

205.2099

Monoisotopic Molecular Weight

205.073893223

IUPAC Name

2-(5-methoxy-1H-indol-3-yl)acetic acid

Traditional Name

5-methoxyindole-3-acetic acid

CAS Registry Number

3471-31-6

SMILES

COC1=CC2=C(NC=C2CC(O)=O)C=C1

InChI Identifier

InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)

InChI Key

COCNDHOPIHDTHK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole-3-acetic acids (CHEBI:28281 )
a small molecule (CPD-12020 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0004096)

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0004096)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0004096)

Source

Endogenous

Endogenous (HMDB: HMDB0004096)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0004096)
Tryptophan Metabolism (HMDB: HMDB0004096)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	144.007	30932474
[M+H]+	Not Available	144.168	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000476

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.7 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.55	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.92 m³·mol⁻¹	ChemAxon
Polarizability	20.73 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]+	146.53	31661259
DarkChem	[M-H]-	145.618	31661259
DeepCCS	[M+H]+	145.261	30932474
DeepCCS	[M-H]-	142.903	30932474
DeepCCS	[M-2H]-	176.767	30932474
DeepCCS	[M+Na]+	151.562	30932474
AllCCS	[M+H]+	144.9	32859911
AllCCS	[M+H-H2O]+	140.7	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.9	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.0	32859911
AllCCS	[M+HCOO]-	146.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxyindoleacetate	COC1=CC2=C(NC=C2CC(O)=O)C=C1	3585.1	Standard polar	33892256
5-Methoxyindoleacetate	COC1=CC2=C(NC=C2CC(O)=O)C=C1	2019.0	Standard non polar	33892256
5-Methoxyindoleacetate	COC1=CC2=C(NC=C2CC(O)=O)C=C1	2152.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxyindoleacetate,1TMS,isomer #1	COC1=CC=C2[NH]C=C(CC(=O)O[Si](C)(C)C)C2=C1	2118.5	Semi standard non polar	33892256
5-Methoxyindoleacetate,1TMS,isomer #2	COC1=CC=C2C(=C1)C(CC(=O)O)=CN2[Si](C)(C)C	2227.9	Semi standard non polar	33892256
5-Methoxyindoleacetate,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2150.1	Semi standard non polar	33892256
5-Methoxyindoleacetate,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2155.3	Standard non polar	33892256
5-Methoxyindoleacetate,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2457.4	Standard polar	33892256
5-Methoxyindoleacetate,1TBDMS,isomer #1	COC1=CC=C2[NH]C=C(CC(=O)O[Si](C)(C)C(C)(C)C)C2=C1	2394.2	Semi standard non polar	33892256
5-Methoxyindoleacetate,1TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CC(=O)O)=CN2[Si](C)(C)C(C)(C)C	2453.3	Semi standard non polar	33892256
5-Methoxyindoleacetate,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2625.2	Semi standard non polar	33892256
5-Methoxyindoleacetate,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2585.0	Standard non polar	33892256
5-Methoxyindoleacetate,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2646.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (2 TMS)	splash10-001i-1492000000-4bb4e49122eeca577f6f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized)	splash10-001i-1492000000-4bb4e49122eeca577f6f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methoxyindoleacetate GC-EI-TOF (Non-derivatized)	splash10-001i-0491000000-3833b4bbd544be9889d4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvl-1910000000-c1f37125fc3b608af61f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5090000000-de75a303e99011a4be34	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxyindoleacetate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOF	splash10-0f6x-0950000000-b35cb5918f36be3e1ed9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOF	splash10-0udl-0900000000-4ecf8c9d3192ce786ee1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOF	splash10-0udi-0900000000-8aed7fec3a54d7bd49ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOF	splash10-0udl-2900000000-d7b7a09d3453a1048a14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOF	splash10-0006-5900000000-de21476dd6d423ce7637	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0190000000-30a337d0188ca2b01e98	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOF	splash10-03di-0900000000-e29f13bccd0ff61f4d73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOF	splash10-03di-0900000000-27318e117029d4756f51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOF	splash10-02u1-0900000000-fc96484038377a19704e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOF	splash10-014i-1900000000-b5ca37dc8dd19df79bca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOF	splash10-014i-7900000000-ceb8e6c122bb9a4d3fbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOF	splash10-0002-1910000000-8fd2478b70c897657b7f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOF	splash10-0002-1900000000-7fd87377f29173005ec3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOF	splash10-000i-9700000000-a4cf39ea98f467ad9511	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOF	splash10-000i-9200000000-db11b5a046b68c168da7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOF	splash10-05n1-9100000000-0ff3c25c94ca7b6e75da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-IT , positive-QTOF	splash10-03di-0900000000-0c8ed04608a5330c9d3a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate 60V, Positive-QTOF	splash10-014i-7900000000-95cba07fd384f9f59f79	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxyindoleacetate 40V, Positive-QTOF	splash10-014i-1900000000-23403ec6bee04579f899	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 10V, Positive-QTOF	splash10-000i-0920000000-a3ced0adb5929f6c9416	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 20V, Positive-QTOF	splash10-03dr-0900000000-24447a7e06d2aa011318	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 40V, Positive-QTOF	splash10-0hjj-1900000000-2026293826cbb03562de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 10V, Negative-QTOF	splash10-0w29-0790000000-8c87e508e08c958691a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 20V, Negative-QTOF	splash10-0w2i-0940000000-0373da6c43af5609fec7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 40V, Negative-QTOF	splash10-052o-1900000000-44a6d63553f83a5e7004	2017-09-01	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

Cytoplasm

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected and Quantified	1.09 +/- 2.13 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	details

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

FDB023312

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

VMH ID

5MOXACT

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Higa S, Markey SP: Identification and quantification of 5-methoxyindole-3-acetic acid in human urine. Anal Biochem. 1985 Jan;144(1):86-93. [PubMed:2580458 ]
Meatherall R, Sharma P: Foxy, a designer tryptamine hallucinogen. J Anal Toxicol. 2003 Jul-Aug;27(5):313-7. [PubMed:12908946 ]
Sergeeva TI, Raushenbakh TI, Shevchenko MO, Rybal'chenko VG: [Excretion of 5-hydroxyindole-3-acetic and 5-methoxyindole-3-acetic acids in cancer patients]. Vopr Onkol. 1987;33(10):20-5. [PubMed:2446428 ]

Enzymes

Enzyme Details

1. Acetylserotonin O-methyltransferase

General function:: Involved in O-methyltransferase activity
Specific function:: Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:: ASMT
Uniprot ID:: P46597
Molecular weight:: 41660.34

Reactions

S-Adenosylmethionine + 5-Hydroxyindoleacetic acid → S-Adenosylhomocysteine + 5-Methoxyindoleacetate	details

Showing metabocard for 5-Methoxyindoleacetate (HMDB0004096)

MOL for HMDB0004096 (5-Methoxyindoleacetate)

3D MOL for HMDB0004096 (5-Methoxyindoleacetate)

3D SDF for HMDB0004096 (5-Methoxyindoleacetate)

3D-SDF for HMDB0004096 (5-Methoxyindoleacetate)

PDB for HMDB0004096 (5-Methoxyindoleacetate)

3D PDB for HMDB0004096 (5-Methoxyindoleacetate)

SMILES for HMDB0004096 (5-Methoxyindoleacetate)

INCHI for HMDB0004096 (5-Methoxyindoleacetate)

Structure for HMDB0004096 (5-Methoxyindoleacetate)

3D Structure for HMDB0004096 (5-Methoxyindoleacetate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions