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Showing NP-Card for 2-Aminophenol (NP0002694)

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Record Information
Version1.0
Created at2020-11-23 19:38:08 UTC
Updated at2021-08-19 23:59:15 UTC
NP-MRD IDNP0002694
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Aminophenol
Provided ByBMRBBMRB logo
Description2-Aminophenol, also known as 2-aminobenzenol or 2-hydroxyaniline, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. 2-Aminophenol exists in all living organisms, ranging from bacteria to humans. 2-Aminophenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 1992 (PMID: 1395635). Based on a literature review a significant number of articles have been published on 2-Aminophenol (PMID: 17984079) (PMID: 11304127) (PMID: 24124510) (PMID: 24571346).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002694 (2-Aminophenol)


     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.1719   -0.7765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7883   -1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672    0.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998    1.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    1.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    0.2773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -2.2279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -2.8842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -2.0892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136    0.8135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4787    2.9212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604    1.7286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
M  END
Download

3D MOL for NP0002694 (2-Aminophenol)

NP0002694
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.9813    1.0868   -0.1948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734    0.5539   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435    1.3884    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826    0.8220    0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8769   -0.5440    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -1.3562    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -0.8169   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363   -1.6159   -0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119    0.5988    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1107    1.9887   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    2.4685    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    1.4723    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755   -0.9875    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -2.4383    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -2.6206   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
M  END
Download

3D SDF for NP0002694 (2-Aminophenol)


     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.1719   -0.7765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7883   -1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672    0.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998    1.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    1.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    0.2773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -2.2279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -2.8842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -2.0892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136    0.8135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4787    2.9212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604    1.7286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
M  END
> <DATABASE_ID>
NP0002694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2

> <INCHI_KEY>
CDAWCLOXVUBKRW-UHFFFAOYSA-N

> <FORMULA>
C6H7NO

> <MOLECULAR_WEIGHT>
109.1259

> <EXACT_MASS>
109.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.156512219698374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminophenol

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.8407545403333332

> <ALOGPS_LOGS>
0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.349432320471696

> <JCHEM_PKA_STRONGEST_BASIC>
4.517244574079329

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
32.7393

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminophenol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002694 (2-Aminophenol)

NP0002694
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.9813    1.0868   -0.1948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734    0.5539   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435    1.3884    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826    0.8220    0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8769   -0.5440    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -1.3562    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -0.8169   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363   -1.6159   -0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119    0.5988    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1107    1.9887   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    2.4685    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    1.4723    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755   -0.9875    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -2.4383    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -2.6206   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
M  END
Download

PDB for NP0002694 (2-Aminophenol)

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  O   UNK     0       3.907   0.531   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       6.574   2.071   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.574   0.531   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.241  -0.239   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.908  -0.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.241  -1.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908  -1.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -2.549   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    3                                                            
CONECT    3    2    4    5                                                  
CONECT    4    1    3    6                                                  
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0002694 (2-Aminophenol)

COMPND    NP0002694
HETATM    1  N1  UNL     1      -1.981   1.087  -0.195  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.673   0.554  -0.063  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.444   1.388   0.067  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.683   0.822   0.191  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.877  -0.544   0.193  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.761  -1.356   0.063  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.505  -0.817  -0.064  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.636  -1.616  -0.195  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.812   0.599   0.193  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.111   1.989  -0.692  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.273   2.468   0.064  1.00  0.00           H  
HETATM   12  H4  UNL     1       2.546   1.472   0.291  1.00  0.00           H  
HETATM   13  H5  UNL     1       2.876  -0.987   0.293  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.864  -2.438   0.059  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.604  -2.621  -0.205  1.00  0.00           H  
CONECT    1    2    9   10
CONECT    2    3    3    7
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8
CONECT    8   15
END
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SMILES for NP0002694 (2-Aminophenol)

NC1=CC=CC=C1O
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INCHI for NP0002694 (2-Aminophenol)

InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
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View in JSmol
Synonyms
ValueSource
2-AminobenzenolChEBI
2-HydroxyanilineChEBI
O-AminophenolChEBI
O-HydroxyanilineChEBI
ortho-AminophenolMeSH
2-Aminophenol, ion (1+)MeSH
2-Aminophenol, hydrochlorideMeSH
2-Aminophenol, monopotassium saltMeSH
2-Aminophenol, monosodium saltMeSH
Chemical FormulaC6H7NO
Average Mass109.1259 Da
Monoisotopic Mass109.05276 Da
IUPAC Name2-aminophenol
Traditional Name2-aminophenol
CAS Registry NumberNot Available
SMILES
NC1=CC=CC=C1O
InChI Identifier
InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
InChI KeyCDAWCLOXVUBKRW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Species Where Detected
Species NameSourceReference
Pseudomonas pseudoalcaligenesKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point174.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point234.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility20000 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP0.620The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.35ALOGPS
logP0.84ChemAxon
logS0.02ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)4.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability11.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0240309
DrugBank IDDB01726
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093591
KNApSAcK IDC00007533
Chemspider ID5596
KEGG Compound IDC01987
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Aminophenol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18112
Good Scents IDrw1171141
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Wulferink M, Gonzalez J, Goebel C, Gleichmann E: T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome. Chem Res Toxicol. 2001 Apr;14(4):389-97. doi: 10.1021/tx000214u. [PubMed:11304127 ]
  3. Basketter DA, Liden C: Further investigation of the prohapten concept: reactions to benzene derivatives in man. Contact Dermatitis. 1992 Aug;27(2):90-7. doi: 10.1111/j.1600-0536.1992.tb05216.x. [PubMed:1395635 ]
  4. Chirino B, Strahsburger E, Agullo L, Gonzalez M, Seeger M: Genomic and functional analyses of the 2-aminophenol catabolic pathway and partial conversion of its substrate into picolinic acid in Burkholderia xenovorans LB400. PLoS One. 2013 Oct 4;8(10):e75746. doi: 10.1371/journal.pone.0075746. eCollection 2013. [PubMed:24124510 ]
  5. Capello MC, Broquier M, Ishiuchi S, Sohn WY, Fujii M, Dedonder-Lardeux C, Jouvet C, Pino GA: Fast nonradiative decay in o-aminophenol. J Phys Chem A. 2014 Mar 20;118(11):2056-62. doi: 10.1021/jp411457v. Epub 2014 Mar 10. [PubMed:24571346 ]