NP-MRD: Showing NP-Card for acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate (NP0265055)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 08:54:05 UTC

Updated at

2022-09-08 08:54:05 UTC

NP-MRD ID

NP0265055

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate

Description

O-acetyl tryptophol belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate was first documented in 1985 (PMID: 16664264). Based on a literature review a small amount of articles have been published on O-acetyl tryptophol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    5.3373   -1.5791    1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814   -0.8886    0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956   -0.4543   -0.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2075   -0.6980    0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012   -0.0527   -0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1284    0.3733   -1.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411    0.1533   -0.8398 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6136    0.8263   -2.0134 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    0.8185    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911    0.9671    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5883    2.1262    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9024    1.8796    0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9180    2.7838   -0.1312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    0.5632    0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2472   -0.1819    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1423   -1.5407    0.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -2.0968    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203   -1.3754    0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8361   -0.0293    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9722   -2.3452    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790   -2.0913    1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462   -0.8545    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727   -0.8618   -0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456    1.7309   -2.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.7009   -2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9047    0.1689    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0281    1.8174    0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1505    3.0973   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    3.7796   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.3094    0.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568   -2.0955    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -3.1374    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7408   -1.8134    0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 10  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652309082210542D          

 19 20  0  0  0  0            999 V2000
    4.8525   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -2.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.8511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -2.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.0261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2256   -0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0326    0.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3681    0.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451   -0.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2521   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5070   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8930   -1.1867    0.0000 C   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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  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  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10 19  1  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265055

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(=O)C(N)CC1=CN(O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O4/c1-8(16)19-13(17)11(14)6-9-7-15(18)12-5-3-2-4-10(9)12/h2-5,7,11,18H,6,14H2,1H3

> <INCHI_KEY>
IEXCUYUXJYLXHI-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O4

> <MOLECULAR_WEIGHT>
262.265

> <EXACT_MASS>
262.095356939

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.45733539446782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
acetyl 2-amino-3-(1-hydroxy-1H-indol-3-yl)propanoate

> <JCHEM_LOGP>
0.414898297333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.111700814484347

> <JCHEM_PKA_STRONGEST_BASIC>
6.867475357556287

> <JCHEM_POLAR_SURFACE_AREA>
94.55

> <JCHEM_REFRACTIVITY>
68.8164

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.058  -1.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.392  -2.359   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.392  -3.899   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.725  -1.589   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.059  -2.359   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.059  -3.899   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.393  -1.589   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      14.393  -0.049   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.060  -1.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.221  -0.057   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      18.727   0.263   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      19.354   1.670   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      19.497  -1.071   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.004  -1.391   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.480  -2.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.449  -4.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.943  -3.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.467  -2.215   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   10   14                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄N₂O₄

Average Mass

262.2650 Da

Monoisotopic Mass

262.09536 Da

IUPAC Name

acetyl 2-amino-3-(1-hydroxy-1H-indol-3-yl)propanoate

Traditional Name

acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC(=O)C(N)CC1=CN(O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C13H14N2O4/c1-8(16)19-13(17)11(14)6-9-7-15(18)12-5-3-2-4-10(9)12/h2-5,7,11,18H,6,14H2,1H3

InChI Key

IEXCUYUXJYLXHI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Alpha-amino acid or derivatives
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Dicarboxylic acid or derivatives
Heteroaromatic compound
Pyrrole
Carboxylic acid anhydride
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
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	0.41	ChemAxon
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	6.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.55 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.82 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

129670515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lacan G, Magnus V, Simaga S, Iskric S, Hall PJ: Metabolism of tryptophol in higher and lower plants. Plant Physiol. 1985 Jul;78(3):447-54. doi: 10.1104/pp.78.3.447. [PubMed:16664264 ]
LOTUS database [Link]

Showing NP-Card for acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate (NP0265055)

MOL for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

3D MOL for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

3D SDF for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

3D-SDF for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

PDB for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

3D PDB for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

SMILES for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

INCHI for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

Structure for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)

3D Structure for NP0265055 (acetyl 2-amino-3-(1-hydroxyindol-3-yl)propanoate)