NP-MRD: Showing NP-Card for Methyl 4-chloro-1H-indole-3-acetate (NP0047497)

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Record Information

Version

1.0

Created at

2022-03-17 20:41:10 UTC

Updated at

2022-03-17 20:41:10 UTC

NP-MRD ID

NP0047497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl 4-chloro-1H-indole-3-acetate

Description

Methyl 4-chloro-1H-indole-3-acetate, also known as 4-chloro-indoleacetic acid methyl ester, 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. Methyl 4-chloro-1H-indole-3-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methyl 4-chloro-1H-indole-3-acetate has been detected, but not quantified in, several different foods, such as broad beans, common pea, grass pea, lentils, and pulses. Methyl 4-chloro-1H-indole-3-acetate is found in Lathyrus latifolius, Lathyrus maritimus, Lathyrus odoratus , Pinus sylvestris , Vicia amurensis and Vicia sativa . This could make methyl 4-chloro-1H-indole-3-acetate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306482D          

 15 16  0  0  0  0            999 V2000
   -0.9851    4.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    2.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1=CNC2=CC=CC(Cl)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H10ClNO2/c1-15-10(14)5-7-6-13-9-4-2-3-8(12)11(7)9/h2-4,6,13H,5H2,1H3

> <INCHI_KEY>
SYPGJEURLIGNPE-UHFFFAOYSA-N

> <FORMULA>
C11H10ClNO2

> <MOLECULAR_WEIGHT>
223.656

> <EXACT_MASS>
223.040006276

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.890012081002315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(4-chloro-1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.459694830666667

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.714733615171085

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0782080280154345

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
58.026

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(4-chloro-1H-indol-3-yl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.839   7.658   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.143   5.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       4.924   5.923   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -0.887   4.729   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.332   7.338   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    7   10                                                       
CONECT    6    7   13                                                       
CONECT    7    5    6   11                                                  
CONECT    8    3   11   12                                                  
CONECT    9    4   11   13                                                  
CONECT   10    5   14   15                                                  
CONECT   11    7    8    9                                                  
CONECT   12    8                                                            
CONECT   13    6    9                                                       
CONECT   14   10                                                            
CONECT   15    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-chloro-1H-indole-3-acetic acid	Generator
1H-Indole-3-acetic acid, 4-chloro-, methyl ester	HMDB
4-Chloro-indoleacetic acid methyl ester	HMDB
4-Chloroindole-3-acetic acid methyl ester	HMDB
4-Chloroindolyl-3-acetic acid methyl ester	HMDB
Methyl (4-chloro-1H-indol-3-yl)acetate	HMDB
Methyl 4-chloroindolyl-3-acetate	HMDB
Methyl 2-(4-chloro-1H-indol-3-yl)acetic acid	Generator

Chemical Formula

C₁₁H₁₀ClNO₂

Average Mass

223.6560 Da

Monoisotopic Mass

223.04001 Da

IUPAC Name

methyl 2-(4-chloro-1H-indol-3-yl)acetate

Traditional Name

methyl 2-(4-chloro-1H-indol-3-yl)acetate

CAS Registry Number

19077-78-2

SMILES

COC(=O)CC1=CNC2=CC=CC(Cl)=C12

InChI Identifier

InChI=1S/C11H10ClNO2/c1-15-10(14)5-7-6-13-9-4-2-3-8(12)11(7)9/h2-4,6,13H,5H2,1H3

InChI Key

SYPGJEURLIGNPE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lathyrus latifolius	Plant	KNApSAcK
Lathyrus maritimus	Plant	KNApSAcK
Lathyrus odoratus	Plant	KNApSAcK
Lathyrus sativus	FooDB	KNAPSACK
Lens culinaris	FooDB	KNAPSACK
Pinus sylvestris	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Vicia amurensis	Plant	KNApSAcK
Vicia faba	FooDB	KNAPSACK
Vicia sativa	Plant	KNApSAcK

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
Aryl chloride
Aryl halide
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

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	3.26	ALOGPS
logP	2.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.03 m³·mol⁻¹	ChemAxon
Polarizability	21.89 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

HMDB0032937

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010922

KNApSAcK ID

C00000103

Chemspider ID

141665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methyl 4-chloro-1H-indole-3-acetate (NP0047497)

MOL for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

3D MOL for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

3D SDF for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

3D-SDF for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

PDB for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

3D PDB for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

SMILES for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

INCHI for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

Structure for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)

3D Structure for NP0047497 (Methyl 4-chloro-1H-indole-3-acetate)