NP-MRD: Showing NP-Card for 1H-Indole-3-acetamide (NP0000051)

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Record Information

Version

1.0

Created at

2012-09-11 17:32:20 UTC

Updated at

2021-08-19 20:22:31 UTC

NP-MRD ID

NP0000051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1H-Indole-3-acetamide

Description

Indole-3-acetamide, also known as 2-(3-indolyl)acetamide or IAM, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-acetamide has been detected, but not quantified, in several different foods, such as Alaska wild rhubarbs, lingonberries, butternut squash, pineapples, and agaves. Indole-3-acetamide is also found in the common pea and has been isolated from the etiolated seedlings of the black gram (Phaseolus mungo).

Structure

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


  Mrv1652306242117433D          

 23 24  0  0  0  0            999 V2000
   -3.9515    0.2860    0.0231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638    0.3560    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    1.4022   -0.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -0.5932    0.9035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2634   -0.1634    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.3585    2.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285    0.6332    1.6958 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    0.2982    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093    0.3607   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192   -0.0588   -1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -0.5554   -2.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100   -0.6410   -1.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514   -0.2066   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4546   -0.4993   -0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6269    1.0321    0.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0252   -0.8901    1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7075   -1.5461    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.5456    3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    1.0383    2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8403    0.7542   -0.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044    0.0067   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338   -0.8912   -3.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4423   -1.0265   -1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  6 18  1  0  0  0  0
  7 19  1  0  0  0  0
  9 20  1  0  0  0  0
 10 21  1  0  0  0  0
 11 22  1  0  0  0  0
 12 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C(=O)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)

> <INCHI_KEY>
ZOAMBXDOGPRZLP-UHFFFAOYSA-N

> <FORMULA>
C10H10N2O

> <MOLECULAR_WEIGHT>
174.1992

> <EXACT_MASS>
174.079312952

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.225110654059137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1H-indol-3-yl)acetamide

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.9028134846666664

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.93598196036075

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.943467257936039

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7379629363377562

> <JCHEM_POLAR_SURFACE_AREA>
58.88

> <JCHEM_REFRACTIVITY>
50.27430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -3.951   0.286   0.023  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.564   0.356   0.222  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.998   1.402  -0.267  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.694  -0.593   0.904  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.263  -0.163   0.925  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.357   0.359   2.031  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.629   0.633   1.696  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.841   0.298   0.390  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.909   0.361  -0.455  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.819  -0.059  -1.754  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.621  -0.555  -2.217  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.510  -0.641  -1.405  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.651  -0.207  -0.109  0.00  0.00           C+0
HETATM   14  H   UNK     0      -4.455  -0.499  -0.483  0.00  0.00           H+0
HETATM   15  H   UNK     0      -4.627   1.032   0.369  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.025  -0.890   1.929  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.708  -1.546   0.312  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.044   0.546   3.030  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.354   1.038   2.315  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.840   0.754  -0.065  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.704   0.007  -2.408  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.534  -0.891  -3.240  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.442  -1.026  -1.743  0.00  0.00           H+0
CONECT    1    2   14   15                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16   17                                             
CONECT    5    4    6   13                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12    5    8                                                  
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    4                                                            
CONECT   17    4                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    9                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
1H-Indole-3-acetamide	ChEBI
3-Indoleacetamide	ChEBI
Indoleacetamide	ChEBI
(indol-3-yl)Acetamide	HMDB
1-Indole-3-acetamide	HMDB
2-(1H-indol-3-yl)Acetamide	HMDB
2-(3-Indolyl)acetamide	HMDB
3-Indolylacetamide	HMDB
IAM	HMDB
Indole-3-acetamide (6ci,8ci)	HMDB
Indole-3-acetamide (8ci)	HMDB
TSC	HMDB
TSR	HMDB
Auxin amide	HMDB
Indole-3-acetamide	HMDB, KEGG

Chemical Formula

C₁₀H₁₀N₂O

Average Mass

174.1992 Da

Monoisotopic Mass

174.07931 Da

IUPAC Name

2-(1H-indol-3-yl)acetamide

Traditional Name

indole-3-acetamide

CAS Registry Number

879-37-8

SMILES

[H]N([H])C(=O)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

InChI Identifier

InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)

InChI Key

ZOAMBXDOGPRZLP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Balansia epichloe	LOTUS Database	35616633
Citrus unshiu	KNApSAcK Database	22123792
Cucurbita maxima	LOTUS Database	35616633
Dysidea etheria	-	KNApSAcK
Euphorbia escula	KNApSAcK Database	22123792
Phaseolus mungo	KNApSAcK Database	22123792
Pisum sativum	KNApSAcK Database	22123792
Pseudomonas savastanoi	LOTUS Database	35616633
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Species Where Detected

Species Name	Source	Reference
Dryocosmus kuriphilus	KNApSAcK Database	22123792
Streptomyces atroolivaceus	KNApSAcK Database	22123792
Streptomyces mutabilis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:16031 )
acetamides (CHEBI:16031 )
a small molecule (CPD-237 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	150 - 151 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13440 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	15.94	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.88 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.27 m³·mol⁻¹	ChemAxon
Polarizability	18.23 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

HMDB0029739

DrugBank ID

DB08652

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Tsavkelova E, Oeser B, Oren-Young L, Israeli M, Sasson Y, Tudzynski B, Sharon A: Identification and functional characterization of indole-3-acetamide-mediated IAA biosynthesis in plant-associated Fusarium species. Fungal Genet Biol. 2012 Jan;49(1):48-57. doi: 10.1016/j.fgb.2011.10.005. Epub 2011 Nov 4. [PubMed:22079545 ]
Dimkpa CO, Zeng J, McLean JE, Britt DW, Zhan J, Anderson AJ: Production of indole-3-acetic acid via the indole-3-acetamide pathway in the plant-beneficial bacterium Pseudomonas chlororaphis O6 is inhibited by ZnO nanoparticles but enhanced by CuO nanoparticles. Appl Environ Microbiol. 2012 Mar;78(5):1404-10. doi: 10.1128/AEM.07424-11. Epub 2011 Dec 30. [PubMed:22210218 ]
Mano Y, Nemoto K: The pathway of auxin biosynthesis in plants. J Exp Bot. 2012 May;63(8):2853-72. doi: 10.1093/jxb/ers091. Epub 2012 Mar 23. [PubMed:22447967 ]
Kulkarni GB, Sanjeevkumar S, Kirankumar B, Santoshkumar M, Karegoudar TB: Indole-3-acetic acid biosynthesis in Fusarium delphinoides strain GPK, a causal agent of Wilt in Chickpea. Appl Biochem Biotechnol. 2013 Feb;169(4):1292-305. doi: 10.1007/s12010-012-0037-6. Epub 2013 Jan 11. [PubMed:23306880 ]
Gaweska HM, Taylor AB, Hart PJ, Fitzpatrick PF: Structure of the flavoprotein tryptophan 2-monooxygenase, a key enzyme in the formation of galls in plants. Biochemistry. 2013 Apr 16;52(15):2620-6. doi: 10.1021/bi4001563. Epub 2013 Apr 4. [PubMed:23521653 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for 1H-Indole-3-acetamide (NP0000051)

MOL for NP0000051 (1H-Indole-3-acetamide)

3D MOL for NP0000051 (1H-Indole-3-acetamide)

3D SDF for NP0000051 (1H-Indole-3-acetamide)

3D-SDF for NP0000051 (1H-Indole-3-acetamide)

PDB for NP0000051 (1H-Indole-3-acetamide)

3D PDB for NP0000051 (1H-Indole-3-acetamide)

SMILES for NP0000051 (1H-Indole-3-acetamide)

INCHI for NP0000051 (1H-Indole-3-acetamide)

Structure for NP0000051 (1H-Indole-3-acetamide)

3D Structure for NP0000051 (1H-Indole-3-acetamide)