NP-MRD: Showing NP-Card for 5-Methoxy-3-indoleacetic acid (NP0002855)

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Record Information

Version

2.0

Created at

2020-11-23 19:42:06 UTC

Updated at

2021-08-12 19:52:20 UTC

NP-MRD ID

NP0002855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Methoxy-3-indoleacetic acid

Provided By

BMRB

Description

5-Methoxyindoleacetate 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-Methoxyindoleacetate exists in all living organisms, ranging from bacteria to humans. In humans, 5-methoxyindoleacetate is involved in the tryptophan metabolism pathway. 5-Methoxyindoleacetate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 5-Methoxy-3-indoleacetic acid is found in Daphnia pulex. 5-Methoxy-3-indoleacetic acid was first documented in 1985 (PMID: 2580458). Based on a literature review very few articles have been published on 5-Methoxyindoleacetate (PMID: 2446428).

Structure

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


     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.3367    1.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420    1.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853    0.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232   -0.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664   -2.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718   -1.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223   -2.9071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363   -2.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8544   -0.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    0.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9069    1.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3674    1.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725    2.9133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3662   -0.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4631    3.1812    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103    0.1918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8314    1.5602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1179   -0.9023    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043   -3.3648    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6351   -4.3954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4939   -2.8216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    1.4098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747   -0.6426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4987    4.0074    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1473    2.0656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  2  0
 15  3  1  0
 14  6  1  0
  1 16  1  6
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  6
 10 24  1  0
 13 25  1  0
 15 26  1  0
M  END
> <DATABASE_ID>
NP0002855

> <DATABASE_NAME>
NP-MRD

> <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    NP0002855
HETATM    1  C1  UNL     1      -3.920   1.937  -0.128  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.529   1.786  -0.271  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.818   0.619  -0.163  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.469  -0.570   0.108  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.689  -1.708   0.202  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.324  -1.631   0.031  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.656  -2.571   0.082  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.836  -2.021  -0.139  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.699  -0.648  -0.355  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.784   0.320  -0.642  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.125   1.200   0.474  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.305   2.018   0.967  1.00  0.00           O  
HETATM   13  O3  UNL     1       4.391   1.149   1.027  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.334  -0.441  -0.241  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.444   0.688  -0.336  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.462   1.802  -1.107  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.349   1.197   0.570  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.173   2.932   0.320  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.551  -0.638   0.244  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.207  -2.629   0.409  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.462  -3.561   0.269  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.808  -2.526  -0.161  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.685  -0.291  -0.955  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.553   0.923  -1.567  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.230   1.044   0.508  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.068   1.618  -0.550  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

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 Mass

205.2099 Da

Monoisotopic Mass

205.07389 Da

IUPAC Name

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

Traditional Name

5-methoxyindole-3-acetic acid

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, ethanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, ethanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, ethanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0004096

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1016/0003-2697(85)90087-9. [PubMed:2580458 ]
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 ]

Showing NP-Card for 5-Methoxy-3-indoleacetic acid (NP0002855)

MOL for NP0002855 (5-Methoxy-3-indoleacetic acid)

3D MOL for NP0002855 (5-Methoxy-3-indoleacetic acid)

3D SDF for NP0002855 (5-Methoxy-3-indoleacetic acid)

3D-SDF for NP0002855 (5-Methoxy-3-indoleacetic acid)

PDB for NP0002855 (5-Methoxy-3-indoleacetic acid)

3D PDB for NP0002855 (5-Methoxy-3-indoleacetic acid)

SMILES for NP0002855 (5-Methoxy-3-indoleacetic acid)

INCHI for NP0002855 (5-Methoxy-3-indoleacetic acid)

Structure for NP0002855 (5-Methoxy-3-indoleacetic acid)

3D Structure for NP0002855 (5-Methoxy-3-indoleacetic acid)