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Showing NP-Card for Hydroxymethyl indol-3-yl ketone (NP0049180)

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Record Information
Version2.0
Created at2022-03-17 21:08:23 UTC
Updated at2022-03-17 21:08:23 UTC
NP-MRD IDNP0049180
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxymethyl indol-3-yl ketone
DescriptionHydroxymethyl indol-3-yl ketone, also known as 3-(hydroxyacetyl)indole or 2-hydroxy-1-(1H-indol-3-yl)-ethanone, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Hydroxymethyl indol-3-yl ketone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hydroxymethyl indol-3-yl ketone has been detected, but not quantified in, mushrooms. Hydroxymethyl indol-3-yl ketone is found in Lactarius deliciosus , Malassezia furfur, Prionitis lanceolata, Streptomyces sp., Streptomyces staurosporeus, Tedania ignis and Wallemia sebi. This could make hydroxymethyl indol-3-yl ketone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049180 (Hydroxymethyl indol-3-yl ketone)


  Mrv0541 05061310332D          

 13 14  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
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    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
    1.1387    0.8555    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
    0.8838    0.0709    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
   -0.1781   -0.8853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    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
  7  3  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
M  END
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3D MOL for NP0049180 (Hydroxymethyl indol-3-yl ketone)

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3D SDF for NP0049180 (Hydroxymethyl indol-3-yl ketone)

  Mrv0541 05061310332D          

 13 14  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
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    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
    1.1387    0.8555    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
    0.8838    0.0709    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
   -0.1781   -0.8853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    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
  7  3  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c12-6-10(13)8-5-11-9-4-2-1-3-7(8)9/h1-5,11-12H,6H2

> <INCHI_KEY>
IBLZDDPFMAFWKP-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.022118940493574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1-(1H-indol-3-yl)ethan-1-one

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
0.8124072816666665

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.887871689929828

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.970763314133286

> <JCHEM_PKA_STRONGEST_BASIC>
-3.348616101667295

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
49.2495

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1-(1H-indol-3-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049180 (Hydroxymethyl indol-3-yl ketone)
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PDB for NP0049180 (Hydroxymethyl indol-3-yl ketone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         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       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   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      -0.332  -1.653   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   11                                                       
CONECT    6   10   12                                                       
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    4    7   11                                                  
CONECT   10    6    8   13                                                  
CONECT   11    5    9                                                       
CONECT   12    6                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0049180 (Hydroxymethyl indol-3-yl ketone)
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SMILES for NP0049180 (Hydroxymethyl indol-3-yl ketone)
OCC(=O)C1=CNC2=CC=CC=C12
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INCHI for NP0049180 (Hydroxymethyl indol-3-yl ketone)
InChI=1S/C10H9NO2/c12-6-10(13)8-5-11-9-4-2-1-3-7(8)9/h1-5,11-12H,6H2
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View in JSmol
Synonyms
ValueSource
3-(Hydroxyacetyl)indoleHMDB
3-(Hydroxylacetyl)-indoleHMDB
2-Hydroxy-1-(1H-indol-3-yl)-ethanoneHMDB
2-Hydroxy-1-(1H-indol-3-yl)ethanoneHMDB
2-Hydroxy-1-(1H-indol-3-yl)ethanone, 9ciHMDB
3-GlyceroindoleHMDB
Hydroxymethyl indol-3-yl ketone, 8ciHMDB
INDOLE-3-ketolHMDB
Chemical FormulaC10H9NO2
Average Mass175.1840 Da
Monoisotopic Mass175.06333 Da
IUPAC Name2-hydroxy-1-(1H-indol-3-yl)ethan-1-one
Traditional Name2-hydroxy-1-(1H-indol-3-yl)ethanone
CAS Registry Number2400-51-3
SMILES
OCC(=O)C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO2/c12-6-10(13)8-5-11-9-4-2-1-3-7(8)9/h1-5,11-12H,6H2
InChI KeyIBLZDDPFMAFWKP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Lactarius deliciosusFungi
Malassezia furfurLOTUS Database
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Prionitis lanceolataLOTUS Database
Streptomyces sp.Bacteria
Streptomyces staurosporeusBacteria
Tedania ignisLOTUS Database
Wallemia sebiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct ParentIndoles  
Alternative Parents
Substituents
  • Indole
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Alpha-hydroxy ketone
    • 

  • Pyrrole
    • 

  • Vinylogous amide
    • 

  • Heteroaromatic compound
    • 

  • Ketone
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.23ALOGPS
logP0.81ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.97ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.25 m³·mol⁻¹ChemAxon
Polarizability18.02 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038628  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018022  
KNApSAcK IDNot Available
Chemspider ID173681  
KEGG Compound IDNot Available
BioCyc IDINDOLE-3-KETOL  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound200631  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available