NP-MRD: Showing NP-Card for 1H-Indol-3-ylacetyl-myo-inositol (NP0046119)

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Record Information

Version

1.0

Created at

2022-03-17 19:48:46 UTC

Updated at

2022-03-17 19:48:47 UTC

NP-MRD ID

NP0046119

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1H-Indol-3-ylacetyl-myo-inositol

Description

1H-Indol-3-ylacetyl-myo-inositol 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. 1H-Indol-3-ylacetyl-myo-inositol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1H-Indol-3-ylacetyl-myo-inositol is found, on average, in the highest concentration within rices. 1H-Indol-3-ylacetyl-myo-inositol has also been detected, but not quantified in, cereals and cereal products and corns. This could make 1H-indol-3-ylacetyl-myo-inositol a potential biomarker for the consumption of these foods. A cyclitol ester that is 1D-myo-inositol bearing a indol-3-acetyl substituent at position 1.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309182008382D          

 24 26  0  0  1  0            999 V2000
    8.3258  -13.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0709  -14.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6229  -14.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4299  -14.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5452  -12.5499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1328  -13.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6848  -13.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4385  -13.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3522  -12.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1530  -13.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8659  -13.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8659  -12.7127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0103  -14.7819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4395  -13.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5849  -12.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0102  -11.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4395  -12.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0116  -13.9592    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7261  -13.5468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7261  -12.7216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0116  -12.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2970  -12.7216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2970  -13.5467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5848  -13.9578    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
 11 12  2  0  0  0  0
 10 11  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 13  1  1  0  0  0
 19 14  1  6  0  0  0
 20 17  1  1  0  0  0
 21 16  1  6  0  0  0
 22 15  1  6  0  0  0
 23 24  1  6  0  0  0
 11 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO7/c18-10(5-7-6-17-9-4-2-1-3-8(7)9)24-16-14(22)12(20)11(19)13(21)15(16)23/h1-4,6,11-17,19-23H,5H2/t11-,12-,13+,14-,15-,16-/m1/s1

> <INCHI_KEY>
XUACNUJFOIKYPQ-BKQXGZDCSA-N

> <FORMULA>
C16H19NO7

> <MOLECULAR_WEIGHT>
337.3246

> <EXACT_MASS>
337.116151967

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.16263332084478

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl 2-(1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-1.4077824289999994

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.98298219882113

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.34930086487974

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6457985567809814

> <JCHEM_POLAR_SURFACE_AREA>
143.24

> <JCHEM_REFRACTIVITY>
80.7349

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl 1H-indol-3-ylacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  C   UNK     0      15.541 -25.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.066 -26.545   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.096 -27.689   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.602 -27.369   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      17.818 -23.426   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      17.048 -24.760   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.078 -25.905   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.485 -25.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.324 -23.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.819 -26.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.150 -25.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      22.150 -23.730   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      26.153 -27.593   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      28.820 -26.055   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      23.492 -22.978   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      26.152 -21.440   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      28.820 -22.978   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      26.155 -26.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.489 -25.287   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.489 -23.747   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.155 -22.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.821 -23.747   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.821 -25.287   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      23.492 -26.055   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   12   10   24                                                  
CONECT   12   11                                                            
CONECT   13   18                                                            
CONECT   14   19                                                            
CONECT   15   22                                                            
CONECT   16   21                                                            
CONECT   17   20                                                            
CONECT   18   19   23   13                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21   17                                                  
CONECT   21   20   22   16                                                  
CONECT   22   21   23   15                                                  
CONECT   23   18   22   24                                                  
CONECT   24   23   11                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Indol-3-ylacetyl-1D-myo-inositol	ChEBI, HMDB
Indol-3-ylacetyl-myo-inositol	ChEBI, HMDB
Indole-3-acetyl-1D-myo-inositol	ChEBI, HMDB
Indole-3-acetyl-myo-inositol	ChEBI, HMDB
Indole-3-ylacetyl-myo-inositol	ChEBI, HMDB
1D-1-O-(indol-3-yl)acetyl-myo-inositol	HMDB
1H-Indol-3-ylacetyl-myo-inositol	HMDB

Chemical Formula

C₁₆H₁₉NO₇

Average Mass

337.3246 Da

Monoisotopic Mass

337.11615 Da

IUPAC Name

(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl 2-(1H-indol-3-yl)acetate

Traditional Name

(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl 1H-indol-3-ylacetate

CAS Registry Number

73925-84-5

SMILES

O[C@H]1[C@H](O)[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H19NO7/c18-10(5-7-6-17-9-4-2-1-3-8(7)9)24-16-14(22)12(20)11(19)13(21)15(16)23/h1-4,6,11-17,19-23H,5H2/t11-,12-,13+,14-,15-,16-/m1/s1

InChI Key

XUACNUJFOIKYPQ-BKQXGZDCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Cyclohexanol
Cyclitol or derivatives
Benzenoid
Substituted pyrrole
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:15711 )
indoleacetic acid ester conjugate (CHEBI:15711 )
cyclitol ester (CHEBI:15711 )

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	-0.17	ALOGPS
logP	-1.4	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.35	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	143.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.73 m³·mol⁻¹	ChemAxon
Polarizability	33.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon