NP-MRD: Showing NP-Card for 3-Indole carboxylic acid glucuronide (NP0339207)

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Record Information

Version

2.0

Created at

2024-09-11 20:24:49 UTC

Updated at

2024-09-11 20:24:49 UTC

NP-MRD ID

NP0339207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Indole carboxylic acid glucuronide

Description

3-Indole carboxylic acid glucuronide, also known as 3-indoleformate glucuronide, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. 3-Indole carboxylic acid glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Indole carboxylic acid glucuronide is a burnt and mothball tasting compound. Outside of the human body,.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016502D          

 24 26  0  0  1  0            999 V2000
    3.3523    1.9354    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
    2.6378    0.6979    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
    2.6378    2.3479    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
    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 N   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
    0.0768    3.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    3.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    4.3727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739    4.5442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190    5.3289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6710    5.9420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4780    5.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    4.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300    6.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    7.1682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370    6.2120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    6.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    5.5004    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  6  0  0  0
 15 23  1  1  0  0  0
 14 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0339207

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO8/c17-9-10(18)12(13(20)21)23-15(11(9)19)24-14(22)7-5-16-8-4-2-1-3-6(7)8/h1-5,9-12,15-19H,(H,20,21)/t9-,10-,11+,12?,15-/m0/s1

> <INCHI_KEY>
BDNWJTRKUBXAGH-DOVARBIBSA-N

> <FORMULA>
C15H15NO8

> <MOLECULAR_WEIGHT>
337.2815

> <EXACT_MASS>
337.079766461

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.03828364333073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.018202838333332964

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.856966534314665

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2930996338716634

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869065425044596

> <JCHEM_POLAR_SURFACE_AREA>
149.31

> <JCHEM_REFRACTIVITY>
76.6993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       6.258   3.613   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       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   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       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.143   5.873   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.680   6.698   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.204   8.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.698   8.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.222   9.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.253  11.092   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.759  10.771   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.235   9.307   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.789  11.916   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.314  13.381   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.296  11.596   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.777  12.556   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.284  10.267   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.332   7.338   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
3-Indole carboxylate glucuronide	Generator
Indole-3-carboxylate glucuronide	HMDB
1H-Indole-3-carboxylate glucuronide	HMDB
1H-Indole-3-carboxylic acid glucuronide	HMDB
3-Indole carboxylic acid glucuronoside	HMDB
3-Indolecarboxylate glucuronide	HMDB
3-Indolecarboxylic acid glucuronide	HMDB
3-Indoleformate glucuronide	HMDB
3-Indoleformic acid glucuronide	HMDB
3-Indolylcarboxylate glucuronide	HMDB
3-Indolylcarboxylic acid glucuronide	HMDB
Indole-3 carboxylate glucuronide	HMDB
Indole-3-carboxilic acid-O-glucuronide	HMDB
Indole-3-carboxylic acid glucuronide	HMDB
Indole-3-carboxylic acid glucuronoside	HMDB
Indole-3-carboxylicacid glucuronide	HMDB
(3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylate	Generator

Chemical Formula

C₁₅H₁₅NO₈

Average Mass

337.2815 Da

Monoisotopic Mass

337.07977 Da

IUPAC Name

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

Traditional Name

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C15H15NO8/c17-9-10(18)12(13(20)21)23-15(11(9)19)24-14(22)7-5-16-8-4-2-1-3-6(7)8/h1-5,9-12,15-19H,(H,20,21)/t9-,10-,11+,12?,15-/m0/s1

InChI Key

BDNWJTRKUBXAGH-DOVARBIBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Pentose phosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Long-chain fatty acid
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Hydroxy fatty acid
Monoalkyl phosphate
Thia fatty acid
Fatty acid
Imidolactam
Fatty amide
Alkyl phosphate
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Azole
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid
Carbothioic s-ester
Amino acid or derivatives
Thiocarboxylic acid ester
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxide
Organooxygen compound
Carbonyl group
Organonitrogen compound
Alcohol
Amine
Organopnictogen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxygen compound
Primary 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	-0.14	ALOGPS
logP	-0.018	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	32.04 Å³	ChemAxon
Number of Rings	3	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

HMDB0013189

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029324

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

53481645

PDB ID

Not Available

ChEBI ID

68486

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-Indole carboxylic acid glucuronide (NP0339207)

MOL for NP0339207 (3-Indole carboxylic acid glucuronide)

3D MOL for NP0339207 (3-Indole carboxylic acid glucuronide)

3D SDF for NP0339207 (3-Indole carboxylic acid glucuronide)

3D-SDF for NP0339207 (3-Indole carboxylic acid glucuronide)

PDB for NP0339207 (3-Indole carboxylic acid glucuronide)

3D PDB for NP0339207 (3-Indole carboxylic acid glucuronide)

SMILES for NP0339207 (3-Indole carboxylic acid glucuronide)

INCHI for NP0339207 (3-Indole carboxylic acid glucuronide)

Structure for NP0339207 (3-Indole carboxylic acid glucuronide)

3D Structure for NP0339207 (3-Indole carboxylic acid glucuronide)