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Showing NP-Card for Dioxindole-3-acetic acid (NP0049278)

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Record Information
Version1.0
Created at2022-03-17 21:09:54 UTC
Updated at2022-03-17 21:09:54 UTC
NP-MRD IDNP0049278
Secondary Accession NumbersNone
Natural Product Identification
Common NameDioxindole-3-acetic acid
DescriptionDioxindole-3-acetic acid 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. Dioxindole-3-acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dioxindole-3-acetic acid has been detected, but not quantified in, sunflowers. This could make dioxindole-3-acetic acid a potential biomarker for the consumption of these foods. Dioxindole-3-acetic acid can be found in sunflower, which makes dioxindole-3-acetic acid a potential biomarker for the consumption of this food product. Those are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Dioxindole-3-acetic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Dioxindole-3-acetic acid is found in Prunus cerasus. Dioxindole-3-acetic acid belongs to indolyl carboxylic acids and derivatives class of compounds.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049278 (Dioxindole-3-acetic acid)


  Mrv1652310101705532D          

 15 16  0  0  0  0            999 V2000
    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
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    0.4430    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.3820    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    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -0.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
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3D MOL for NP0049278 (Dioxindole-3-acetic acid)

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3D SDF for NP0049278 (Dioxindole-3-acetic acid)

  Mrv1652310101705532D          

 15 16  0  0  0  0            999 V2000
    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
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    0.4430    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.3820    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    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -0.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1(O)C(O)=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO4/c12-8(13)5-10(15)6-3-1-2-4-7(6)11-9(10)14/h1-4,15H,5H2,(H,11,14)(H,12,13)

> <INCHI_KEY>
MHLHEINWUCSPTL-UHFFFAOYSA-N

> <FORMULA>
C10H9NO4

> <MOLECULAR_WEIGHT>
207.1828

> <EXACT_MASS>
207.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.473739611094203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,3-dihydroxy-3H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
-0.08

> <JCHEM_LOGP>
0.8753023726666663

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.028933765103905

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.382551688279522

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2707067741009711

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
52.426899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2,3-dihydroxyindol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049278 (Dioxindole-3-acetic acid)
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PDB for NP0049278 (Dioxindole-3-acetic acid)
HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.792   0.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.792  -0.713   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -0.542  -1.483   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126  -1.483   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.752   0.190   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8   10                                                       
CONECT    6    3    7   10                                                  
CONECT    7    4    6   11                                                  
CONECT    8    5   12   13                                                  
CONECT    9   10   11   14                                                  
CONECT   10    5    6    9   15                                             
CONECT   11    7    9                                                       
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0049278 (Dioxindole-3-acetic acid)
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SMILES for NP0049278 (Dioxindole-3-acetic acid)
OC(=O)CC1(O)C(O)=NC2=CC=CC=C12
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INCHI for NP0049278 (Dioxindole-3-acetic acid)
InChI=1S/C10H9NO4/c12-8(13)5-10(15)6-3-1-2-4-7(6)11-9(10)14/h1-4,15H,5H2,(H,11,14)(H,12,13)
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Synonyms
ValueSource
Dioxindole-3-acetateGenerator
Chemical FormulaC10H9NO4
Average Mass207.1828 Da
Monoisotopic Mass207.05316 Da
IUPAC Name2-(2,3-dihydroxy-3H-indol-3-yl)acetic acid
Traditional Name(2,3-dihydroxyindol-3-yl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1(O)C(O)=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO4/c12-8(13)5-10(15)6-3-1-2-4-7(6)11-9(10)14/h1-4,15H,5H2,(H,11,14)(H,12,13)
InChI KeyMHLHEINWUCSPTL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Helianthus annuus L.FooDB
Prunus cerasusLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolyl carboxylic acids and derivatives  
Direct ParentIndolyl carboxylic acids and derivatives  
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
    • 

  • Indole
    • 

  • Dihydroindole
    • 

  • Benzenoid
    • 

  • Tertiary alcohol
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.08ALOGPS
logP0.88ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-0.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.43 m³·mol⁻¹ChemAxon
Polarizability19.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0176485  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018478  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10488522  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available